阅读说明：本技术 作为添味剂的不饱和内酯 (Unsaturated lactones as odorants ) 是由 贝恩德·霍尔斯彻 马克·曼斯菲尔德 托拜厄斯·瓦格纳 于 2012-09-14 设计创作，主要内容包括：本发明主要涉及式(Ia)化合物或式(Ib)化合物,涉及包含式(Ia)化合物或式(Ib)化合物的混合物或由式(Ia)化合物或式(Ib)化合物组成的混合物,并且还涉及包含一定量的根据本发明所述的式(Ia)化合物或(Ib)化合物或所述的混合物的加香产品。本发明还涉及本发明的化合物、根据本发明所述的混合物和/或本发明的产品用作添味剂和/或添味剂混合物和/或添味剂产品的用途。在进一步的方面,本发明涉及一种用于赋予气味的方法和一种用于生产本发明的化合物的方法。(The present invention relates mainly to compounds of formula (Ia) or compounds of formula (Ib), to mixtures comprising or consisting of compounds of formula (Ia) or compounds of formula (Ib), and also to perfumed products comprising an amount of a compound of formula (Ia) or a compound of formula (Ib) or said mixtures according to the invention. The invention also relates to the use of a compound according to the invention, a mixture according to the invention and/or a product according to the invention as an odorant and/or an odorant mixture and/or an odorant product. In further aspects, the invention relates to a method for imparting odor and a method for producing the compounds of the invention.)

1. A product consisting of or comprising

(a) One, two or more compounds of formula (Ia) or (Ib)

Wherein in each of formulae (Ia) and (Ib), X and the wavy line are, independently of one another, as follows

Said X is a methylene or ethylene group, and

the wavy line indicates that the configuration at the associated double bond is an E or Z configuration,

and is

Wherein in said formula (Ia), the configuration at the carbon atom having the number 14 is R or S,

and

(b) one, two or more compounds other than the compound of formula (Ia) or (Ib), the compound or compounds being selected from the group consisting of odorants,

provided that

The compound or one, two or more of these compounds is a musk odorant compound or musk odorant compounds,

or

The compound or one, two or more of the compounds is/are an odorant or odorants with a woody odor profile

Or

The compound or one, two or more of the compounds being an odorant or odorants with floral odor notes

Or

The compound or one, two or more of these compounds is an odorant or odorants with green, fruity odor notes.

2. The product according to claim 1, wherein the compound of formula (Ia) or (Ib) is selected from the group

3. A product according to claim 1, wherein ingredient (a) is at least one, two or more of said compounds of formula (Ia) wherein X has the same definition for said one, two or all of these compounds and is a methylene group,

and/or

The E isomer as well as the Z isomer of the compound of formula (Ia), wherein X has the same definition for both the E isomer and the Z isomer and is a methylene or ethylene group,

and/or

Two enantiomers of said pair of enantiomers of a compound of formula (Ia),

and/or

The E isomer and the Z isomer of the compound of formula (Ib), wherein X has the same definition for both the E isomer and the Z isomer and is a methylene or ethylene group

4. The product according to claim 1 wherein the musk odorant compound is a macrocyclic musk odorant compound.

5. The product of claim 1, wherein

The total amount of compounds of formula (Ia) and/or compounds of formula (Ib) is in the range of from 0.00001 to 99.9 wt. -%, based on the total amount of the product,

and/or

The weight ratio of the total amount of compound of formula (Ia) and/or compound of formula (Ib) to the total amount of other odorants which are not compounds of formula (Ia) and/or (Ib) based on the total amount of the product is in the range of 1: 1000 to 1: 0.5, or higher.

6. A product according to claim 5 wherein the total amount of compounds of formula (Ia) and/or (Ib) is in the range 0.001 to 70 wt%.

7. The product of claim 1, comprising

(c) One or more carriers for component (a) and/or component (b), and/or

(d) One, two or more compounds selected from the group consisting of water, ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1, 2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate and triacetin, and/or

(e) One, two or more components selected from the group consisting of

(e1) Surfactants and other base materials, adjuvants and ingredients for use in perfumed products

And

(e2) base substances, auxiliaries and ingredients for use in products for nutrition, oral care or pleasure.

8. The product according to claim 7, wherein the carrier or carriers of component (c) is or are selected from the group consisting of (A) porous inorganic materials and (B) organic materials, preferably one or more of which is or comprises a plastic or other organic polymer.

9. The product according to any one of claims 1 to 8, selected from: shampoos, perfume extracts, perfumes, eau de toilette, shaving lotions, colognes, pre-shave products, spray colognes, fragrance refreshing wipes, acidic cleaning products, alkaline cleaning products and neutral cleaning products, fabric refreshers, easy-to-iron products, liquid laundry detergents, powder laundry detergents, laundry pretreatment products, laundry fabric softeners, washing soaps, washing tablets, disinfectants, surface disinfectants, air fresheners, sprays, waxes and polishes, personal care products, hand creams and paints, foot creams and paints, depilatory creams and paints, after-shave creams and paints, tanning creams and paints, hair care products, deodorants and antiperspirants, decorative cosmetic products, candles, lamp oils, fragrances, insecticides, insect repellents and propellants.

10. A compound of formula (Ia) or (Ib)

Wherein in each of formulae (Ia) and (Ib), X and the wavy line are, independently of one another, as follows

Said X is a methylene or ethylene group, and

the wavy line indicates that the configuration at the associated double bond is an E or Z configuration,

and is

Wherein in said formula (Ia), the configuration at the carbon atom having the number 14 is R or S,

use of a product according to any one of claims 1 to 8

For replacing musk odorants, musk odorant mixtures or musk odorant products having poor adhesion and/or poor affinity and/or poor biodegradability

And/or

For enhancing and/or modifying the odor tonality,

-for providing skin and/or textile fibers and/or for providing skin and/or textile fibers with one or more odor profiles selected from musk, gloss, softness, woody, sexual, floral and delightful

-as an agent for increasing the substantivity and/or retention of an odorant mixture and/or as an immobilizing agent and/or agent for enhancing the odor of other odorants perceived by an aqueous solution comprising a surfactant.

11. Use according to claim 10, wherein the enhanced and/or modified odour notes are selected from one or more odour notes of the group consisting of musk, gloss, gentleness, woody, sexual, floral and delightful.

12. Use according to claim 11, wherein the odour notes are selected from musks.

13. A method for enhancing an odor having one, two or more or all of the following odor tonality: woody, floral, fresh, green, fruity, musk and spicy; the method comprises the following steps:

producing or providing one or more products not comprising a compound of formula (Ia) and a compound of formula (Ib) according to claim 1 or 2

Or

Providing human or animal skin or human or animal hair,

(ii) production or provision of

-a product according to any of claims 1 to 8,

(iii) (iii) mixing or contacting the article produced or provided in steps (i) and (ii),

wherein the amount of the product produced in step (ii) for use in step (iii) is sufficient to enhance one, two or more or all of the following odor notes: woody, floral, fresh, green, fruity, musk and spicy.

Technical Field

The present invention relates to a compound of formula (Ia) or a compound of formula (Ib), to a mixture comprising or consisting of a compound of formula (Ia) or a compound of formula (Ib), and also to a perfumed product comprising an amount, preferably a perceived effect, of a compound of formula (Ia) or a compound of formula (Ib) or said mixture according to the invention.

The invention also relates to the use of a compound according to the invention, a mixture according to the invention and/or a product according to the invention as an odorant and/or an odorant mixture and/or an odorant product.

In further aspects, the invention relates to a method for imparting odor and a method for producing the compounds of the invention.

Other aspects and particularly preferred aspects of the invention will become apparent from the following description and from the appended claims.

Background

Despite the diversity of existing odorants, there is a general need in the perfumery industry for odorants that impart new odor notes (note) on the one hand or known odor notes by new compounds on the other hand. In general, for example, there is a need for compounds that impart musk odor notes. Compounds (odorants) of particular interest are those which, in addition to imparting a musk odour note, can impart a further pleasant odour note in the product. It is particularly desirable that the different aspects of odor and odor tonality overlap, thus producing an overall composite perceived odor. More particularly, there is interest in odorants having a musk odor profile that is capable of forming a synergistic combination with floral fragrance odorants and that, when formed, produces a pleasant, complex perceived odor. Such compounds and their innovative or original odor profile and complex perceived odor extend the possibilities available to perfumers. Suitable odorants should be preferred, as well as musk odour notes should be preferred, with further odour notes and aspects, and thereby imparting novel flavour compositions with odour notes and complex properties.

In addition to the appropriate odor qualities of the compounds as odorants, further important implications relate to additional secondary qualities. These ancillary qualities include qualities such as stability, compatibility with other compounds in the perfume composition, productivity, solubility, biodegradability, and unobjectionable toxicology. Other qualities of interest relate to the adhesion, retention or substantivity of the odorant, in particular on the fibers and/or hair. This quality is particularly important for surfactant-containing products such as shampoos, laundry detergents and fabric softeners.

Adhesion is a term used for the inherent ability of a compound to adhere to a substrate. Affinity or retention is a term used to refer to the ability of a compound to appear in one phase (usually the aqueous phase) and reach the substrate or even remain on the substrate after, for example, a washing or rinsing process. This effect is particularly manifested on substrates such as skin, hair and textile fibers (e.g. wool, cotton, hemp, synthetic fibers). The terms "affinity" and "retention" are for example fully elucidated in EP 1201738A 1 (see paragraphs [0004] - [0005] therein). Generally, odorants with high affinity or retention are sought after.

Methods of identifying compounds with the above beneficial qualities are often laborious and not suitable for prediction, since

The mechanism of odor perception is not yet fully known,

the relationship between the specific perception of odour on the one hand (odour recognition) and the chemical structure of the relevant odorant on the other hand has not been fully studied, and

even small changes in the structural composition of known odorants will usually result in drastic changes in perceptual quality and are usually detrimental to the tolerance of the human body (i.e. they diminish tolerance).

Known compounds that impart musk odour notes have been described in our own earlier studies and results, in particular as follows:

EP 0908455B 1 relates to an odorant composition comprising 13-methyloxacyclopentadec-10-en-2-one. Our own studies have shown that these compounds generally impart powdery, musk, lactone-like, fruity odor notes.

EP 0424787B 1 relates to a mixture comprising at least 60 wt% (based on the weight of the mixture) of pentadecenyllactide (pentadecenolides) and further ingredients. Our investigations show that such mixtures generally impart an amber musk type note, fruity note, pear-like flavor note.

The main object of the present invention is to identify new odorant compounds which impart a musky odor note, preferably in combination with additional advantageous and original odor qualities. Moreover, these compounds will enable novel and original perfumed products to have specific odor profiles and aspects and/or to have specific odor complexes. It is a particular object of the present invention to identify odorants which impart musk odour notes and which have in a beneficial manner one, two or all of the preferred secondary qualities identified above and/or indicated below, and which are, in addition, suitable for use in combination with odorants which impart floral and/or green fruity notes (green fruity odour notes are erroneously perceived as both green and fruity odour notes) and/or woody odour notes. Preferred secondary properties are, in particular, (i) greater stability under defined conditions of use, (ii) higher productivity, (iii) improved adhesion, (iv) high affinity, (v) pronounced boosting or strong rejuvenation (bloming), (vi) better skin-and toxicology properties relative to comparable odorants, and (vii) high retention.

This object is achieved according to the invention by a compound of the formula (Ia) or a compound of the formula (Ib)

Wherein in each of formulae (Ia) and (Ib), X and the wavy line are, independently of one another, as follows

X is a methylene or ethylene group, and

the wavy line indicates that the configuration at the associated double bond is either the E or Z configuration,

and is

Wherein in said formula (Ia), the configuration at the carbon atom having the number 14 is R or S.

The compounds of formula (Ia) and (Ib) according to the invention are each defined as cyclic, unsaturated lactones.

In our own studies, it has been surprisingly found that the compounds of the invention impart one, two, more or all of the following odor notes: musk, glossy, soft, aucklandia root, sexy, flowery scent and delightful; in particular musk; and is particularly suitable in combination with odorants imparting floral and/or woody and/or green fruit aroma tonality. Together with the desired (and also the aforementioned) odour qualities, the compounds of formula (Ia) or (Ib) according to the invention also have in particular one, two or all, respectively, of the abovementioned auxiliary qualities, which are usually present in a manner superior to the auxiliary qualities of other compounds having very similar or identical odour qualities.

The results are surprising, the macrocyclic musk compounds are generally regarded as having been intensively studied and the unsaturated lactones of the formulae (Ia) and (Ib) according to the invention represent new, useful odorants having a musky odor profile. The compounds of formula (Ia) and of formula (Ib) according to the invention have quite distinct olfactory qualities which are distinctly different from and in some cases exceed those of known odorants. The fact that these compounds of the invention have the desired properties described above is unexpected and particularly surprising.

The odor properties of the compounds of the present invention are described in our own survey conducted by a trained panel of tests as musk, shiny, soft, woody, sexual, floral and/or cheerful. The compounds of the present invention are reminiscent of the odor profile of musk seed oil and impart a very natural perceived odor.

The compounds of formula (Ia) according to the invention have a chiral centre at carbon atom 14. These compounds are therefore either in the S or R configuration.

As described above, the wavy line indicates that the configuration at the associated double bond is an E configuration or a Z configuration. Thus, the compounds of formula (Ia), which may be in both the S and R configurations, and the compounds of formula (Ib) are in the E or Z configuration.

Preferred compounds of formula (Ia) and (Ib) according to the invention (as described above) are those selected from the following group:

according to one preferred use, compounds of formula (Ia) and compounds of formula (Ib) are preferred, wherein X is a methylene group (X ═ CH) for all compounds of formula (Ia) and for all compounds of formula (Ib)₂). According to a further preferred use, preferred compounds of formula (Ia) and compounds of formula (Ib) are: for all compounds of formula (Ia) and for all compounds of formula (Ib) wherein X is ethylene (X ═ C)₂H₄) Those compounds of (1).

Wherein X is a methylene group (X ═ CH)₂) The compounds of the formula (Ia) are particularly preferred since, in our own studies, they impart the desired odor profile in a particularly advantageous manner, in addition to the desired (above) secondary qualities.

Depending on the desired use, compounds of the formula (Ib) may also be preferred.

The invention also relates to mixtures comprising or consisting of two or more compounds of the invention (as described above). The statements made above apply correspondingly to the compounds of the formula (Ia) and/or compounds of the formula (Ib) which are preferably present.

The mixtures according to the invention (as described above) are in principle preferred, said mixtures

-comprising one said compound or compounds of formula (Ia) and one said compound or compounds of formula (Ib), wherein X has the same definition for all compounds of formula (Ia) and compounds of formula (Ib) and is a methylene or ethylene group

And/or

-comprises two or more of said compounds of formula (Ia) wherein X has the same definition for two or all of these compounds and is a methylene group

And/or

-comprises the E isomer as well as the Z isomer of the compound of formula (Ia), wherein X has the same definition for both the E isomer and the Z isomer and is a methylene or ethylene group

And/or

-comprises both enantiomers of said pair of enantiomers of the compound of formula (Ia) as defined above, preferably racemates of both enantiomers of said compound of formula (Ia) as defined above,

and/or

-comprises the E isomer as well as the Z isomer of the compound of formula (Ib), wherein X has the same definition for both the E isomer and the Z isomer and is a methylene or ethylene group.

In a preferred use, the mixture according to the invention (as described above) comprises one said compound of formula (Ia) or two or more said compounds of formula (Ia) and one said compound of formula (Ib) or two or more said compounds of formula (Ib), wherein X has the same definition for all compounds of formula (Ia) and compounds of formula (Ib) and is a methylene group. Such a mixture according to the invention preferably comprises all compounds of formula (Ia) wherein X is a methylene group and all compounds of formula (Ib) wherein X is a methylene group, i.e. such a preferred mixture according to the invention comprises:

a compound of the formula (Ia-1) and

a compound of the formula (Ia-2) and

a compound of the formula (Ia-5) and

a compound of the formula (Ia-6) and

a compound of the formula (Ib-1) and

a compound of the formula (Ib-2).

Preferred mixtures according to the invention (as described above) comprise: two or more of said compounds of formula (Ia) wherein X has the same definition for two or all of these compounds and is a methylene group; and/or the E isomer and the Z isomer of the compound of formula (Ia), wherein X has the same definition for both the E isomer and the Z isomer and is a methylene group.

In a particularly preferred embodiment, the mixture according to the invention (as described above, preferably as defined above as preferred) comprises the E isomer as well as the Z isomer of the compound of formula (Ia), wherein X has the same definition for both the E isomer and the Z isomer and is a methylene group.

The following mixtures are given by way of example as preferred combinations of compounds of formula (Ia) which are particularly suitable for the purposes of the present invention (as described herein) and are accordingly preferred:

a compound of formula (Ia-1) and a compound of formula (Ia-5), or

A compound of formula (Ia-1) and a compound of formula (Ia-6), or

A compound of formula (Ia-2) and a compound of formula (Ia-5), or

A compound of formula (Ia-2) and a compound of formula (Ia-6).

In a further, likewise preferred embodiment, the mixture according to the invention (as described above, preferably as defined above as preferred) comprises (i) two E isomers of the compound of formula (Ia) and/or (ii) two Z isomers of the compound of formula (Ia), wherein X has the same definition for both E isomers and both Z isomers and is a methylene group.

The following mixtures are further preferred combinations of compounds of formula (Ia) given by way of example, which are particularly suitable and correspondingly preferred for the purposes of the present invention (as described herein):

a compound of formula (Ia-1) and a compound of formula (Ia-2), or

A compound of formula (Ia-5) and a compound of formula (Ia-6), or

A compound of the formula (Ia-1), a compound of the formula (Ia-2), a compound of the formula (Ia-5) and a compound of the formula (Ia-6).

In a further, likewise preferred embodiment, the mixture according to the invention (as described above, preferably as defined above as preferred) comprises

(i) The E isomer of the compound of formula (Ia) and both Z isomers of the compound of formula (Ia), wherein X has the same definition for both the E isomer and the Z isomer and is a methylene group,

or

(ii) Two E isomers of the compound of formula (Ia) and one Z isomer of the compound of formula (Ia), wherein X has the same definition for both E isomers and one Z isomer and is a methylene group.

The following mixtures are further preferred combinations of compounds of formula (Ia) given by way of example, which are particularly suitable and correspondingly preferred for the purposes of the present invention (as described herein):

a compound of the formula (Ia-1), a compound of the formula (Ia-2) and a compound of the formula (Ia-5), or

A compound of the formula (Ia-1), a compound of the formula (Ia-2) and a compound of the formula (Ia-6), or

A compound of the formula (Ia-5), a compound of the formula (Ia-6) and a compound of the formula (Ia-1), or

A compound of formula (Ia-5), a compound of formula (Ia-6) and a compound of formula (Ia-2).

In a preferred embodiment that follows, the mixture according to the invention (as described above, preferably as defined above as preferred) comprises the racemate of the compound of formula (Ia).

Of course, in connection with the mixtures described above (and below), it is also the case that they may comprise or comprise not only the above-mentioned compounds of the invention, but also consist only of combinations of these compounds, more particularly those combinations as described above.

Depending on the desired use, the mixtures according to the invention (as described above, preferably as defined above as preferred) may also preferably comprise or consist of the compounds of the formula (Ib). Such mixtures may of course further comprise one or more compounds of formula (I1).

In another preferred use, the mixture according to the invention (as described above) comprises one said compound or two or more said compounds (Ia) and one said compound or two or more said compounds (Ib), wherein X has the same definition for all compounds of formula (Ia) and compounds of formula (Ib) and is an ethylene group. Such a mixture according to the invention preferably comprises all compounds of formula (Ia) wherein X is an ethylene group and all compounds of formula (Ib) wherein X is an ethylene group, i.e. such a preferred mixture according to the invention comprises:

a compound of the formula (Ia-3) and

a compound of the formula (Ia-4) and

a compound of the formula (Ia-7) and

a compound of the formula (Ia-8) and

a compound of the formula (Ib-3) and

compounds of formula (Ib-4).

A further aspect of the invention relates to a product consisting of or comprising

(a) One, two or more compounds of the invention, preferably at least

One, two or more of said compounds of formula (Ia), wherein X has the same definition for said one, two or all of these compounds and is a methylene group,

and/or

The E isomer as well as the Z isomer of the compound of formula (Ia), wherein X has the same definition for both the E isomer and the Z isomer and is a methylene or ethylene group,

and/or

Both enantiomers of said pair of enantiomers of the compound of formula (Ia) of the invention (as defined above, preferably as defined above as preferred), preferably the racemates of both enantiomers of said compound of formula (Ia) of the invention (as defined above, preferably as defined above as preferred),

and/or

The E isomer and the Z isomer of the compound of formula (Ib), wherein X has the same definition for both the E isomer and the Z isomer and is a methylene or ethylene group

And

one, two or more additional components.

In our own studies, it was found that such products of the invention which impart a musk odour note (see later parts of the text for details of the product) generally have a pleasant shine and/or a pleasant feel and/or reinforce an existing odour note.

A preferred product according to the invention comprises as ingredient (b) one, two or more compounds (as described above) which are not compounds according to the invention, the compound or compounds being selected from the group consisting of odorants, wherein

(I) The total amount of the compound of the invention (as described above, preferably as defined above) in the product is sufficient to impart one or more of the following odor notes, musk, shine, gentleness, woody, sexual, floral and delightful (eruutant),

and/or

(II) the total amount of compounds in the component (b) in the product is sufficient to impart one, two or more or all of the following odor notes: woody, floral, fresh (fresh), green (green), fruity, musk and spicy (spicy-balsamic) notes, preferably to impart one or all of the following tonality: the costustoot and the flower fragrance,

wherein the total amount of a compound of the invention (as described above, preferably as defined above as preferred) in said product is sufficient to potentiate and/or modify one or more of these tonality(s),

and/or

(III) the total amount of the compound of the invention (as described above, preferably as defined above as preferred) in the product is sufficient to give the product a fresh, clean, harmonious (harmony), lustrous and/or natural impression,

and/or

(IV) the total amount of the compound of the invention (as described above, preferably as defined above as preferred) in the product is sufficient to produce a perceived odour that is stronger, more harmonious, higher, lighter, softer, fuller and/or more natural than a comparative product which has the same ingredients as the product except that it does not contain the compound of the invention (as described above).

By combining the compounds of formula (Ia) and/or (Ib) according to the invention with one, two or more odorants of component (b), it is possible to compose new odorant compositions. In this way, particularly advantageous, new and original odor tonalities can be created and/or combined. Particularly preferred in this respect is the combination with a compound not according to the invention (as described below) and an odorant (more preferably a floral and/or green fruit aroma note) imparting a woody and/or floral and/or green fruit aroma note.

Odorants (component (b)) which are particularly suitable for combination with the compounds of the invention are identified, for example, in the following documents: s.arctander, Perfune and flavour Materials, Vol.I and II, Montclair, N.J.1969, self-published, or K.Bauer et al, Common Fragrance and flavour Materials,4th edition, Wiley-VCH, Weinheim 2001. The following compounds will be specifically mentioned:

odorants present in extracts from natural sources, such as essential oils, extractum, absolute oils, resins, balms, tinctures, such as for example ambergris tincture; amiruis oil; angelica seed oil; angelica root oil; a coarse oil; valerian oil; basil oil; cleaning tree moss with oil; laurel leaf oil; blumea oil; benzoin resin; bergamot oil; beeswax absolute; birch tar oil; bitter almond oil; savory oil; geranium oil; sandalwood oil of Brazil; juniper oil; calamus oil; camphor oil; cananga oil; cardamom oil; balsam of the balsam pear tree; cinnamon oil; cinnamon absolute oil; castor oil; cedar leaf oil; cedar wood oil; rosa oil; citronella oil; lemon oil; balsam of copaiba; balsam of copaiba; coriander oil; wood sesame oil; cumin oil; cypress oil; artemisia annua oil; dill grass oil; dill seed oil; eau de Brouts neat oil; cleaning oak moss oil; olive oil; tarragon oil; lemon eucalyptus oil; eucalyptus oil; anise oil; pine needle oil; white rosin oil; white rosin resin; geranium oil; grapefruit oil; guaiac oil; gule-rue-fat; oil of crura oil; purifying the helichrysum oil; helichrysum oil; ginger oil; iris root neat oil; iris root oil; jasmine absolute oil; calamus oil; blue chamomile oil; roman chamomile oil; carrot seed oil; balsam of the balsam pear tree; pine needle oil; spearmint oil; coriander oil; laodan fat oil; laodan fat absolute oil; laodan resin; mixed lavender absolute oil; lavandin oil; mixed lavender absolute oil; lavender absolute; lemon grass oil; lepidium meyenii Walp oil; lime distilled oil; pressing lime into oil; linalool oil; litsea cubeba oil; laurel leaf oil; nutmeg oil; marjoram oil; citrus oil; sweet osmanthus oil; mimosa absolute; musk oil; musk tincture; sage oil; nutmeg oil; purifying Myrrha with oil; myrrh oil; myrtle oil; clove leaf oil; clove flower oil; neroli oil; purifying Olibanum oil; mastic oil; callus oil; neroli absolute; orange oil; oregano oil; palmarosa oil; patchouli oil; perilla oil; mulu fragrant oil; coriander leaf oil; oleum Rapae; orange leaf oil; peppermint oil; pepper oil; sweet pepper oil; pine oil; peppermint oil; rose absolute oil; rosewood oil; rose essential oil; rosemary essential oil; chia oil; spanish sage oil; sandalwood oil; celery seed oil; lavender oil; anise oil; storax oil; marigold oil; fir needle oil; tea tree essential oil; turpentine oil; thyme oil; turpentine; fenugreek tonka absolute; tuberose absolute oil; vanilla essential oil; violet leaf absolute oil; verbena oil; vetiver oil; juniper berry oil; lees oil; wormwood oil; wintergreen oil; cananga oil; hyssop oil; paguma larvata absolute oil; cinnamon leaf oil; cinnamon bark oil, and odorants present in their fractions, especially odorants isolated therefrom;

-individual odorants selected from the group of hydrocarbons such as, for example, 3-carene, α -pinene, β -pinene, α -terpinene, gamma-terpinene, p-cymene, bisabolene, camphene, caryophyllene, cedrene, farnesene, limonene, longifolene, myrcene, ocimene, valencene, (E, Z) -1,3, 5-undecene, styrene, diphenylmethane;

aliphatic alcohols, such as for example: hexanol; octanol; 3-octanol; 2, 6-dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; (E) -2-hexenol; 1-octen-3-ol; a mixture of 3,4,5,6, 6-pentamethyl-3/4-hepten-2-ol and 3,5,6, 6-tetramethyl-4-methylenehept-2-ol; (E, Z) -2, 6-nonadienol; 3, 7-dimethyl-7-methoxyoct-2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol;

aliphatic aldehydes and acetals thereof, such as, for example: hexanal; heptanal; octanal; nonanal; decanal; undecalaldehyde; dodecanal; 2-methyl octanal; 2-methylnonanal; (E) -2-hexenal; (Z) -4-heptenal; 2, 6-dimethyl-5-heptenal; 10-undecenal; (E) -4-decenal; 2-dodecenal; 2,6, 10-trimethyl-9-undecenal; 2,6, 10-trimethyl-5, 9-undecanedienal; heptanal acetal; 1, 1-dimethoxy-2, 2, 5-trimethyl-4-hexene; citronellyloxyacetaldehyde; 1- (1-methoxypropoxy) - (E/Z) -3-hexene;

aliphatic ketones and oximes thereof, such as for example: 2-heptanone; 2-octanone; 3-octanone; 2-nonanone; 5-methyl-3-heptanone; 5-methyl-3-heptanone oxime; 2,4,4, 7-tetramethyl-6-octen-3-one; 6-methyl-5-hepten-2-one;

aliphatic sulfur-containing compounds, such as, for example, 3-methylthiohexanol; 3-methylthiohexyl acetate; 3-mercaptohexanol; 3-hexyl thioglycolate; 3-mercaptohexyl butyrate; 3-acetylthioacetic acid hexyl ester; 1-menthene-8-thiol;

aliphatic nitriles, such as, for example, 2-nonenenitrile; 2-undecenenitrile; 2-tridecenenitrile; 3, 12-tridecadienylnitrile (3, 12-tridecadienenitrile); 3, 7-dimethyl-2, 6-octadienenitrile; 3, 7-dimethyl-6-octenenitrile;

esters of aliphatic carboxylic acids, such as for example: (E) and (Z) -3-hexenyl formate; ethyl acetoacetate; isoamyl acetate; 3,5, 5-trimethylacetate; 3-methyl-2-butenyl acetate; (E) -2-hexenyl acetate; (E) -and (Z) -3-hexenyl acetate; octyl acetate; 3-octyl acetate; 1-octen-3-yl acetate; ethyl butyrate; butyl butyrate; isoamyl butyrate; hexyl butyrate; (E) -and (Z) -3-hexenyl isobutyrate; hexyl crotonate; ethyl isovalerate; 2-methyl pentanoic acid ethyl ester; ethyl caproate; allyl caproate; ethyl heptanoate; allyl heptanoate; ethyl octanoate; (E, Z) -2, 4-decadienoic acid ethyl ester; 2-octanoic acid methyl ester; 2-nonanoic acid methyl ester; 2-isoamyloxyacetic acid allyl ester; methyl 3, 7-dimethyl-2, 6-octadienoate; 4-methyl-2-pentylcrotonate;

acyclic terpene alcohols such as, for example: geraniol; nerol; lavender alcohol; nerolidol; farnesol; tetrahydrolinalool; tetrahydrogeraniol; 2, 6-dimethyl-7-octen-2-ol; 2, 6-dimethylocten-2-ol; 2-methyl-6-methylene-7-octen-2-ol; 2, 6-dimethyl-5, 7-octadien-2-ol; 2, 6-dimethyl-3, 5-octadien-2-ol; 3, 7-dimethyl-4, 6-octadien-3-ol; 3, 7-dimethyl-1, 5, 7-octatrien-3-ol; 2, 6-dimethyl 2,5, 7-octatrien-1-ol; and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, valerates, caproates, crotonates, tiglates (tiglates) and 3-methyl-2-butenoates;

acyclic terpene aldehydes and ketones, such as for example: citronellal; 7-methoxy-3, 7-dimethyloctanal; 2,6, 10-trimethyl-9-undecenal; geranylacetone; and also the dimethylacetals and diethylacetals of geranial, neral;

cyclic terpene alcohols such as, for example, menthol, isopulegol, α -terpinene, terpinen-4-ol, menthan-8-ol, menthan-1-ol, menthan-7-ol, borneol, isoborneol, linalool oxide, nopol, cedrol, ambroxol, vetiverol, guaiol, and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, valerates, caproates, crotonates, tiglates (tiglinates) and 3-methyl-2-butenoates;

cyclic terpenic aldehydes and ketones such as, for example, menthone, isomenthone, 8-mercaptomethane-3-one (8-mercaptatomenthan-3-one), carvone, camphor, fenchyl ketone, α -ionone, β -ionone, α -n-methylionone, β -n-methylionone, α -isopropylmethylionone, β -isopropylmethylionone, α -irone, β -damascenone, 1- (2,4, 4-trimethyl-2-cyclohexen-1-yl) -2-buten-1-one, 1,3,4,6,7,8a-hexahydro-1,1,5,5-tetramethyl-2H-2,4 a-methanonaphthalen-8 (5H) -one (1,3,4,6,7,8a-hexahydro-1, 5,5-tetramethyl-2H-2,4 a-methanone, 3,6, 7,8 a-methanone, 5, 5-methanone, 2H-2, 4-methanone, 3-methanone, 3, 26-methanone, 3,8 a-methyl-2-methanone, 26-methyl-2-methanone, 26, 2-methanone, 4-methyl-1, 2-methyl;

cyclic alcohols such as, for example: 4-tert-butylcyclohexanol; 3,3, 5-trimethylcyclohexanol; 3-isoborneol cyclohexanol; 2,6, 9-trimethyl-Z2, Z5, E9-cyclododecatrien-1-ol; 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol;

alicyclic alcohols, such as, for example, α,3, 3-trimethylcyclohexylmethanol, 1- (4-isopropylcyclohexyl) ethanol, 2-methyl-4- (2,2, 3-trimethyl-3-cyclopent-1-yl) butanol, 2-methyl-4- (2,2, 3-trimethyl-3-cyclopent-1-yl) -2-buten-1-ol, 3-methyl-5- (2,2, 3-trimethyl-3-cyclopent-1-yl) pent-2-ol, 3-methyl-5- (2,2, 3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol, 3, 3-dimethyl-5- (2,2, 3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol, 1- (2,2, 6-trimethylcyclohexyl) pent-3-ol, 1- (2,2, 6-trimethylcyclohexyl) hex-3-ol;

cyclic and alicyclic ethers such as, for example, eucalyptol, cedryl methyl ether, cyclododecyl ether, 1-dimethoxycyclododecane, (ethoxymethoxy) cyclododecane, α -cedrene epoxy, 3a,6,6,9 a-tetramethyldodecahydronaphtho [2,1-B ] furan, 3 a-ethyl-6, 6,9 a-trimethyldodecahydronaphtho [2,1-B ] furan, 1,5, 9-trimethyl-13-oxabicyclo- [10.1.0] tridec-4, 8-diene, rose oxide, 2- (2, 4-dimethyl-3-cyclohexen-1-yl) -5-methyl-5- (1-methylpropyl) -1, 3-dioxane;

cyclic and macrocyclic ketones, such as for example: 4-tert-butylcyclohexanone; 2,2, 5-trimethyl-5-pentylcyclopentanone; 2-heptyl cyclopentanone; 2-pentylcyclopentanone; 2-hydroxy-3-methyl-2-cyclopenten-1-one; 3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one; 3-methyl-2-pentyl-2-cyclopenten-1-one; 3-methyl-4-cyclopentadecanone; 3-methyl-5-cyclopentadecanone; 3-methylcyclopentadecanone; 4- (1-ethoxyvinyl) -3,3,5, 5-tetramethylcyclohexanone; 4-tert-amylcyclohexanone; 5-cyclohexadecen-1-one; 6, 7-dihydro-1, 1,2,3, 3-pentamethyl-4 (5H) -indanone; 8-cyclohexadecen-1-one; 9-cyclopentadecen-1-one; cyclopentadecanone; cyclohexadecanone;

cycloaliphatic aldehydes, such as for example: 2-methyl-4- (2,2, 6-trimethylcyclohexen-1-yl) -2-butenal; 4- (4-hydroxy-4-methylpentyl) -3-cyclohexenecarbaldehyde; 4- (4-methyl-3-penten-1-yl) -3-cyclohexenecarbaldehyde;

cycloaliphatic ketones, such as for example: 1- (3, 3-dimethylcyclohexyl) -4-penten-1-one; 2, 2-dimethyl-1- (2, 4-dimethyl-3-cyclohexen-1-yl) -1-propanone; 1- (5, 5-dimethyl-1-cyclohexen-1-yl) -4-penten-1-one; 2,3,8, 8-tetramethyl-1, 2,3,4,5,6,7, 8-octahydro-2-naphthylmethylketone; methyl 2,6, 10-trimethyl 2,5, 9-cyclododecatrienyl ketone; tert-butyl (2, 4-dimethyl-3-cyclohexen-1-yl) methanone;

esters of cyclic alcohols, such as for example: 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-amylcyclohexyl acetate; 4-tert-amylcyclohexyl acetate; 3,3, 5-trimethylcyclohexyl acetate; decahydro-2-naphthyl acetate; 2-cyclopentyl crotonate; 3-pentyltetrahydro-2H-pyran-4-ylacetic acid ester; decahydro-2, 5,5,8 a-tetramethyl-2-naphthalenyl acetate; 4, 7-methylene-3 a,4,5,6,7,7 a-hexahydro-5 or 6-indenyl acetate; 4, 7-methylene-3 a,4,5,6,7,7 a-hexahydro-5 or 6-indenylpropanoate; 4, 7-methylene-3 a,4,5,6,7,7 a-hexahydro-5 or 6-indenyl isobutyrate; 4, 7-methyleneoctahydro-5-or 6-indenyl acetate;

esters of cycloaliphatic alcohols, such as, for example, 1-cyclohexylethyl crotonate;

esters of cycloaliphatic carboxylic acids, such as for example: allyl tricyclohexylpropionate; allyl cyclohexyloxy acetate; cis-and trans-methyl dihydrojasmonate; cis-and trans-jasmonic acid methyl ester; 2-hexyl-3-oxocyclopentanecarboxylic acid methyl ester; 2-ethyl-6, 6-dimethyl-2-cyclohexenecarboxylic acid ethyl ester; 2,3,6, 6-tetramethyl-2-cyclohexenecarboxylic acid ethyl ester; 2-methyl-1, 3-dioxolane-2-acetic acid ethyl ester;

araliphatic alcohols, such as for example: benzyl alcohol; 1-phenethyl alcohol; 3-phenylpropanol; 2-phenylpropanol; 2-phenoxyethanol; 2, 2-dimethyl-3-phenylpropanol; 2, 2-dimethyl-3- (3-methylphenyl) propanol; 1, 1-dimethyl-2-phenylethyl alcohol; 1, 1-dimethyl-3-phenylpropanol; 1-ethyl-1-methyl-3-phenylpropanol; 2-methyl-5-phenylpentanol; 3-methyl-5-phenylpentanol; 3-phenyl-2-propen-1-ol; 4-methoxybenzyl alcohol; 1- (4-isopropylphenyl) ethanol;

esters of araliphatic alcohols and of aliphatic carboxylic acids, such as, for example, benzyl acetate, benzyl propionate, phenyl isobutyrate, phenyl isovalerate, phenethyl 2-acetate, phenethyl 2-propionate, phenethyl 2-isobutyrate, phenethyl 2-isovalerate, phenethyl 1-acetate, α -trichloromethylbenzyl acetate, α -dimethylphenylethyl acetate, α -dimethylphenylethyl butyrate, cinnamyl acetate, 2-phenoxyethyl isobutyrate, 4-methoxybenzyl acetate;

araliphatic ethers such as, for example: 2-phenethylmethyl ether; 2-phenethylisoamyl ether; 2-phenethyl-1-ethoxyethyl ether; phenylacetaldehyde dimethyl acetal; phenylacetaldehyde diethyl acetal; hydratropic aldehyde (hydratropic aldehyde) dimethyl acetal; phenylacetaldehyde glycerol acetal; 2,4, 6-trimethyl-4-phenyl-1, 3-dioxane; 4,4a,5,9 b-tetrahydroindeno [1,2-d ] -m-dioxin; 4,4a,5,9 b-tetrahydro-2, 4-dimethylindene [1,2-d ] -m-dioxin;

aromatic and araliphatic aldehydes, such as, for example, benzaldehyde, phenylacetaldehyde, 3-phenylpropylaldehyde, hydratropic aldehyde, 4-methylbenzaldehyde, 3- (4-ethylphenyl) -2, 2-dimethylpropionaldehyde, 2-methyl-3- (4-isopropylphenyl) -propionaldehyde, 2-methyl-3- (4-isobutylphenyl) propionaldehyde, 3- (4-tert-butylphenyl) propionaldehyde, cinnamaldehyde, α -butylcinnamaldehyde, α -hexylcinnamaldehyde, 3-methyl-5-phenylpentanal, 4-methoxybenzaldehyde, 4-hydroxy-3-ethoxybenzaldehyde, 3, 4-methylenedioxybenzaldehyde, 3, 4-dimethoxybenzaldehyde, 2-methyl-3- (4-methoxyphenyl) propionaldehyde, 2-methyl-3- (4-methylenedioxyphenyl) propionaldehyde;

aromatic and araliphatic ketones, such as for example: acetophenone; 4-methylacetophenone; 4-methoxyacetophenone; 4-tert-butyl-2, 6-dimethylacetophenone; 4-phenyl-2-butanone; 4- (4-hydroxyphenyl) -2-butanone; 1- (2-naphthyl) ethanone; 2-benzofuranylethanone; (3-methyl-2-benzofuranyl) ethanone; a benzophenone; 1,1,2,3,3, 6-hexamethyl-5-indanylmethyl ketone; 6-tert-butyl-1, 1-dimethyl-4-indanylmethyl ketone; 1- [2, 3-dihydro-1, 1,2, 6-tetramethyl-3- (1-methylethyl) -1H-5-indenyl ] ethanone; 5',6',7',8' -tetrahydro-3 ',5',5',6',8',8' -hexamethyl-2-naphthalenone;

aromatic and araliphatic carboxylic acids and esters thereof, such as for example: benzoic acid; phenylacetic acid; methyl benzoate; ethyl benzoate; hexyl benzoate; benzyl benzoate; methyl phenylacetate; ethyl phenylacetate; geranyl phenyl acetate; phenyl ethyl phenylacetate; methyl cinnamate; ethyl cinnamate; cinnamic acid benzyl ester; cinnamic acid phenethyl ester; cinnamic acid cinnamyl ester; allyl phenoxyacetate; methyl salicylate; hexyl salicylate; cyclohexyl salicylate; cis-3-hexenylsalicylate; benzyl salicylate; phenethyl salicylate; methyl 2, 4-dihydroxy-3, 6-dimethylbenzoate; 3-phenylglycidic acid ethyl ester; 3-methyl-3-phenylglycidic acid ethyl ester;

nitrogen-containing aromatic compounds, such as for example: 2,4, 6-trinitro-1, 3-dimethyl-5-tert-butylbenzene; 3, 5-dinitro-2, 6-dimethyl-4-tert-butyl acetophenone; cinnamonitrile; 3-methyl-5-phenyl-2-pentenenitrile; 3-methyl-5-phenylpentanenitrile; methyl anthranilate; methyl-N-anthranilate; schiff base of methyl aminobenzoate and 7-hydroxy-3, 7-dimethyloctanal, 2-methyl-3- (4-tert-butylphenyl) propanal or 2, 4-dimethyl-3-cyclohexenecarbaldehyde; 6-isopropylquinoline; 6-isobutylquinoline; 6-sec-butylquinoline; 2- (3-phenylpropyl) pyridine; indole; skatole; 2-methoxy-3-isopropylpyrazine; 2-isobutyl-3-methoxypyrazine;

phenols, phenyl ethers and phenyl esters, such as for example estragole, anethole, eugenyl methyl ether, isoeugenol, isoeugenyl methyl ether, thymol, carvacrol, diphenyl ether, β -naphthyl methyl ether, β -naphthylethyl ether, β -naphthylisobutyl ether, 1, 4-dimethoxybenzene, eugenol acetate, 2-methoxy-4-methylphenol, 2-ethoxy-5- (1-propenyl) phenol, p-tolylphenylacetic acid;

-heterocyclic compounds such as, for example: 2, 5-dimethyl-4-hydroxy-2H-furan-3-one; 2-ethyl-4-hydroxy-5-methyl-2H-furan-3-one; 3-hydroxy-2-methyl-4H-pyran-4-one; 2-ethyl-3-hydroxy-4H-pyran-4-one;

lactones such as, for example: 1, 4-octalactone; 3-methyl-1, 4-octalactone; 1, 4-nonalactone; 1, 4-decalactone; 8-decene-1, 4-lactone; 1, 4-undecalactone; 1, 4-dodecalactone; 1, 5-decalactone; 1, 5-dodecalactone; 4-methyl-1, 4-decalactone; 2, 3-dihydrocoumarin; octahydro coumarin.

Preferred products of the invention (as described above) include combinations of the following two classes of materials: (i) the compounds of the present invention (as described above, preferably as defined above as preferred) and (ii) one, two or more compounds selected from the group consisting of odorants (ingredient (b)) that impart odor notes to woody odor.

The woody odorants particularly suitable for the combination are as follows: sandranol (2-ethyl-4- (2,2, 3-trimethylcyclopent-3-yl) but-2-en-1-ol), Yadmer K (1',1',5',5' -tetramethyl-hexahydrospiro [1, 3-dioxolane-2, 8- '(5' H) -2H-2,4 a-methanonaphthalene) ], Timberol (1- (2,2, 6-trimethylcyclohexyl) hex-3-ol), Iso E Super (2,3,8, 8-tetramethyl-1, 2,3,4,5,6, 8-octahydro-2-naphthylmethyl ketone), isobornyl acetate (2-exo-bornyl acetate), ylanate (2-tert-butylcyclohexyl acetate).

In our own studies, these products comprising (i) a compound of the invention (as described above, preferably as defined above as preferred) and (ii) a combination of one, two or more compounds selected from the group consisting of odorants imparting woody odor notes (ingredient (b)) are often evaluated as having a brighter, more natural, fresher, glossier and cleaner perceived odor than a comparative product, which is identical to the product except that it does not comprise a compound of the invention (as described above).

Other preferred products of the invention (as described above) include combinations of the following two classes of materials: (i) the compounds of the present invention (as described above, preferably as defined above as preferred) and (ii) one, two or more compounds selected from the group consisting of odorants (ingredient (b)) that impart floral odor notes.

Floral odorants particularly suitable in combination are lily of the valley aldehyde (2-methyl-3- (4-tert-butylphenyl) propanal), methyl dihydrojasmonate (methyl (3-oxo-2-pentylcyclopentyl) acetate), massachene alcohol ((4-isopropylcyclohexyl) methanol), linalool (3, 7-dimethyl-1, 6-octadien-3-ol), dihydromyrcenol (2, 6-dimethyl-7-octen-2-ol), citronellol (3, 7-dimethyl-6-octen-1-ol), phenylisohexanol (3-methyl-5-phenylpentanol), 2-phenylethyl alcohol, hydroxycitronelol (3, 7-dimethyl-7-hydroxyoctan-1-al), α -ionone (4- (2,6, 6-trimethylcyclohex-2-enyl) but-3-en-2-one).

In our own studies, these products comprising (i) a compound of the invention (as described above, preferably as defined above as preferred) and (ii) a combination of one, two or more compounds selected from the group consisting of odorants imparting floral odour notes (ingredient (b)) are often evaluated as having a perceived odour that is fresher, more intense, more harmoniously and more lustrous than a comparative product, which is identical to said product except that it does not comprise a compound of the invention (as described above). Furthermore, the floral aspect was generally evaluated as being more rounded.

Other preferred products of the invention (as described above) include combinations of the following two classes of materials: (i) the compound of the present invention (as described above, preferably as defined above as preferred) and (ii) one, two or more compounds selected from the group consisting of odorants (component (b)) that impart a green fruit aroma odor note.

Particularly suitable green fruit aroma and flavor profiles for the combination are vertral (octahydro-1H-4, 7-methylidene-5-carbaldehyde), cis-3-hexen-1-ol, β -damascenone (1- (2,6, 6-trimethylcyclohex-2-enyl) buten-1-one), vertocitral (2, 4-dimethylcyclohex-3-ene-1-carbaldehyde), cyclogalbanate (allyl (cyclohexyloxy) acetate), hexyl acetate.

In our own studies, these products comprising (i) a compound of the invention (as described above, preferably as defined above as preferred) and (ii) a combination of one, two or more compounds selected from the group consisting of odorants imparting a green fruit note odour note (ingredient (b)) were frequently evaluated as having a perceived odour that was more rounded and softer than a comparative product, which was identical to said product except that it did not comprise a compound of the invention (as described above). Furthermore, the combination with an odorant (ingredient (b)) imparting a green fruit aroma tonality generally gives these products a certain gloss and an impression of (more) natural lightness.

Similarly preferred products of the invention (as described above) include combinations of the following two classes of materials: (i) the compounds of the present invention (as mentioned above, preferably as defined above as preferred) and (ii) one, two or more compounds selected from the group consisting of odorants (component (b)) which impart a pungent odor note.

The spicy odorants which are particularly suitable in combination are as follows: eugenol (2-methoxy-4-allylphenol), coumarin (2H-1-benzopyran-2-one), anisaldehyde (4-methoxybenzaldehyde), amyl cinnamic aldehyde (2-pentyl-3-phenyl-2-propenal), isoamyl salicylate (3-methylbutyl salicylate), and cinnamyl alcohol (3-phenyl-2-propen-1-ol).

In our own studies, these products comprising (i) a compound of the invention (as described above, preferably as defined above as preferred) and (ii) a combination of one, two or more compounds selected from the group consisting of odorants imparting pungent odor notes (component (b)) are often evaluated as having a fresher, more harmonious, glossier and more natural perceived odor than a comparative product, which is identical to said product except that it does not comprise a compound of the invention (as described above).

A combination of a compound of the invention (as described above, preferably as defined above as preferred) and one, two or more compounds of the group consisting of an odorant (ingredient (b)) (as described above, preferably as defined above as preferred) is present in a product according to the invention (as described above, preferably as defined above as preferred), which is typically used in a perceptually effective amount.

In a preferred product according to the invention

The total amount of the compounds of the invention is in the range of 0.00001 to 99.9 wt. -%, preferably in the range of 0.001 to 70 wt. -%, more preferably in the range of 0.01 to 50 wt. -%, and/or based on the total amount of the product

The weight ratio of the total amount of the compound of the invention to the total amount of other odorants which are not compounds of the invention, based on the total amount of the product, is in the range of 1: 1000 to 1: 0.5, or higher.

In our own studies, it was found that: in the products of the invention comprising the compounds of the invention in the amounts described above, preferably as defined above as preferred, it is very common that the intensity of the odor tone is enhanced and/or that the overall aspect of the odor tone is assessed as more rounded and/or more harmonious and/or more natural and/or more shiny than in a comparative product which is identical in composition to said product except that it does not comprise the compounds of the invention (as described above). Particularly preferred products of this aspect of the invention are those which combine the abovementioned advantageous effects which are observed even in very small amounts with the compounds of the invention (or the mixtures according to the invention) added.

In particular, if the compounds of the invention are used to enhance and/or tailor the existing odor profile of a product, imparted by one, two or more compounds selected from the group consisting of odorants (ingredient (b)), and/or to render the profile more harmonious and/or to give it more shine, and/or to emphasize one specific odor profile of the odor profiles, then preferred products of the invention comprise a minor amount of the compounds of the invention or the mixtures according to the invention added, preferably in a total amount of from 0.01 to 5 wt.%, more preferably in a range of from 0.1 to 2 wt.%, based on the total amount of the product. In this context, particularly preferred products of the invention (as described above) are those comprising a combination of the following two classes of substances: (i) the compounds of the invention (as mentioned above, preferably as defined above as preferred) and (ii) one, two or more compounds selected from the group consisting of odorants (ingredient (b)) imparting woody, floral, green and/or spicy odor notes, preferably woody and/or floral odor notes.

If the compounds of the invention are present in the products according to the invention in the total amounts specified above, preferably in the preferred total amounts (i.e. preferably the amounts added are correspondingly small), then in some cases, depending on the other ingredients in the product in question (with regard to further ingredients, see later section below), no intrinsic odor tonality is imparted (with regard to intrinsic odor tonality, see earlier section above) and preferably no intrinsic musk odor tonality is imparted.

Thus, a preferred product according to the invention comprises as ingredient (b) one, two or more compounds not belonging to the compounds of the invention, the compound or compounds being selected from the group consisting of odorants,

provided that

The compound or one, two or more of these compounds is a musk odorant compound or musk odorant compounds, preferably a macrocyclic musk odorant compound or macrocyclic musk odorant compounds

Or

The compound or one, two or more of the compounds is/are an odorant or odorants with a woody odor profile

Or

The compound or one, two or more of the compounds being an odorant or odorants with floral odor notes

Or

The compound or one, two or more of the compounds is an odorant or odorants with a green fruit odor note.

The aforementioned musk odorant compounds not belonging to the present invention comprise all compounds that impart a musk odour note and are not compounds of formula (Ia) or (Ib). Preferably, macrocyclic musk odorant compounds not according to the invention are present, more preferably macrocyclic musk odorant compounds not according to the invention and selected from the group consisting of nifanolide (nirvanolides), cyclopentadecanolide (habanolides) and oxacyclohexadecan-2-one (globoids). Particularly preferably, they are macrocyclic musk odorant compounds, not according to the invention and selected from the group consisting of (Z) -13-methyloxacyclopentadec-10-en-2-one, (E, Z) -1-oxacyclohexadec-12/13-en-2-one and (E, Z) -1-oxacyclohexadec-12/13-en-2-one.

For compounds with odorants having woody, floral or green fruit aroma tonality, see the earlier section above.

In our own studies it has been found that in many cases, it is particularly clear that the compounds of the invention comprise as component (b) one, two or more compounds not belonging to the compounds of the invention, the compound or compounds being selected from the group consisting of odorants,

provided that

The compound or one, two or more of these compounds is a musk odorant compound or musk odorant compounds, preferably a macrocyclic musk odorant compound or macrocyclic musk odorant compounds,

the compounds of the present invention show the above-mentioned advantageous effects to a particularly significant extent. In our own studies, this preferred product of the invention is generally evaluated as: is more harmonious and/or more natural and/or stronger and/or brighter and/or more rounded and/or milder than a comparative product which is identical in composition to said product except that it does not comprise a compound according to the invention (as described above).

Preferred products comprise a combination of a compound of the invention (as described above, preferably as defined above as preferred) and one, two or more compounds not belonging to a compound of the invention, the compound or compounds being selected from the group consisting of odorants,

provided that

The compound or one, two or more of these compounds is a musk odorant compound or musk odorant compounds, preferably a macrocyclic musk odorant compound or macrocyclic musk odorant compounds

Or

The compound or one, two or more of the compounds is/are an odorant or odorants with a woody odor profile

Or

The compound or one, two or more of the compounds being an odorant or odorants with floral odor notes

Or

The compound or one, two or more of these compounds is an odorant or odorants with a green fruity odor note,

in our own studies, the preferred products generally differ in that: one, two or all of the above-mentioned ancillary qualities are exhibited in a beneficial manner compared to a comparative product which is identical in composition to the preferred product except that it does not contain a compound of the invention (as described above). These qualities include, inter alia, improved affinity, retention and adhesion.

The products according to the invention, as mentioned above, preferably as defined above, are preferably not only comprised of the compounds of the invention, but also further components. This further component may not only be an odorant of ingredient (b), as described above, but also other/further substances or ingredients.

Preferred products of the invention (as described above, preferably as defined above as preferred) (further) comprise

(c) One or more carriers for component (a) and/or component (b).

In the sense of the present invention, the compound of component (a) is a compound of the present invention, while the compound of component (b) is one, two or more compounds not belonging to the compound of the present invention, the compound or compounds being selected from the group consisting of odorants (other odorants) (in this respect, compare the discussion above).

Preferred products of the invention are such products (as described above, preferably as defined above as preferred)

Wherein the support or supports of the component (c) are selected from the group consisting of (A) porous inorganic materials and (B) organic materials, one or more of which are preferably or comprise plastics or other organic polymers.

The porous inorganic material (A) is, for example, light density sulfate, silica gel, zeolite, gypsum, clay particles, aerated concrete.

The organic material (B) is, for example, wood, cellulose-based substances, sugars, dextrins (e.g. maltodextrin) or plastics, such as PVC, polyvinyl acetate or polyurethanes.

In a preferred product of the invention, the compound of the invention (as defined above, preferably as defined above being preferred) may be adsorbed on a support (as defined above). In our own extensive studies it was found that in many cases a more controlled odor-modified release effect is produced by adsorption of the compounds of the invention on one, two or all of the above carriers than in a comparative product which has the same composition as the preferred product except for the carrier which does not contain ingredient (c).

A further preferred product of the invention comprises

(d) One, two or more compounds selected from the group consisting of water, ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1, 2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate and triacetin.

The compounds of component (d) generally act as solvents and/or diluents in the products according to the invention (as mentioned above, preferably as defined above as preferred).

A particularly preferred solvent and/or agent for dilution is water.

Preferred products according to the invention comprise water in a total amount of up to 99.999999 wt%, preferably 5 to 80 wt%, based on the total weight of the product.

Other preferred products according to the invention (as described above, preferably as defined above as preferred) comprise

(e) One, two or more components selected from the group consisting of

(e1) Surfactants and other base materials, adjuvants and ingredients for use in perfumed products

And

(e2) base substances, auxiliaries and ingredients for use in products for nutrition, oral care or pleasure.

The surfactant (e1) distributed to ingredient (e) is an anionic and/or nonionic and/or amphoteric and/or cationic surfactant.

Examples of suitable anionic surfactants are alkyl sulfates, alkyl ether sulfates, alkyl sulfonates, alkylaryl sulfonates, alkyl succinates, alkyl sulfosuccinates, N-alkanoyl sarcosinates, acyl taurates, acyl isethionates, alkyl phosphates, alkyl ether carboxylates, α -olefin sulfonates, more particularly alkali and alkaline earth metal salts, such as sodium, potassium, magnesium, calcium, and ammonium and triethanolamine salts, the alkyl ether sulfates, alkyl ether phosphates and alkyl ether carboxylates may have between 1 and 10 ethylene oxide or propylene oxide units, preferably between 1 and 3 ethylene oxide units in the molecule.

Examples include sodium lauryl sulfate, ammonium lauryl sulfate, sodium lauryl ether sulfate, ammonium lauryl ether sulfate, sodium lauryl sarcosinate, sodium oleylsuccinate, sodium lauryl sulfosuccinate, sodium dodecylbenzene sulfonate, triethanolamine dodecylbenzene sulfonate.

Examples of suitable nonionic surfactants are the reaction products of aliphatic alcohols or alkylphenols having 6 to 20C atoms in the alkyl chain, which may be linear or branched with ethylene oxide and/or propylene oxide. The amount of alkylene oxide is about 6 to 60 moles per mole of alcohol. Further suitable are alkylamine oxides, monoalkylalkanolamides or dialkylalkanolamides, fatty acid esters of polyethylene glycols, ethoxylated fatty acid amides, alkylpolyglycosides or sorbitan ether esters.

Examples of suitable amphoteric surfactants are alkyl betaines, alkylamidopropyl betaines, alkyl sulphobetaines, alkyl glycinates, alkyl carboxyglycinates, alkyl amphoacetates or alkyl amphopropionates, alkyl amphodiacetates or alkyl amphodipropionates.

For example, coco dimethyl sulfopropyl betaine, lauryl betaine, cocamidopropyl betaine or sodium cocoamphopropionate may be used.

Suitable cationic surfactants are quaternary ammonium compounds, an example being cetyltrimethylammonium chloride.

Particularly preferred products according to the invention comprise one, two or more surfactants. More specifically, such products preferably comprise one of the following combinations of separately identified ingredients:

(i) component (a) and one, two or more surfactants, preferably in further combination with water,

(ii) components (a), (b) and one, two or more surfactants, preferably in further combination with water,

(iii) components (a), (b), (d) and one, two or more surfactants.

In the case where the base substances, adjuvants and ingredients are distributed to ingredient (e) and intended for use in a product for nutrition, oral care or pleasure (e2), the substances in question are preferably a mixture of: fresh or processed, vegetable or animal base material or raw material (such as raw, fried, dried, fermented, smoked and/or boiled meat, bone, cartilage, fish, vegetables, fruits, herbs, nuts, vegetable or fruit juices or pastes or mixtures thereof), digestible or non-digestible carbohydrates (such as sucrose, maltose, fructose, glucose, dextrin, amylose, amylopectin, inulin, xylan, cellulose, tagatose), sugar alcohols (such as sorbitol, erythritol), natural or hydrogenated fats (such as beef tallow, lard, palm oil fat, coconut fat, hydrogenated vegetable fat), oils (such as sunflower oil, peanut oil, corn germ oil, olive oil, fish oil, soybean oil, sesame oil), fatty acids or their salts (such as potassium stearate), proteinogenic or non-proteinogenic amino acids and related compounds (such as, gamma-aminobutyric acid, taurine), peptides (such as glutathione), natural or processed proteins (such as gelatin), enzymes (such as peptidases), nucleic acids, nucleotides, flavoring agents for unpleasant taste sensations, further taste modifiers for other generally unpleasant taste sensations, other taste modifiers (such as inositol phosphates, nucleotides, such as guanosine monophosphate, adenosine monophosphate or other compounds, such as sodium glutamate or 2-phenoxypropionic acid), emulsifying agents (such as lecithin, diacylglycerol, acacia), stabilizing agents (such as carrageenan, alginate), preservatives (such as benzoic acid, sorbic acid), antioxidants (such as tocopherol, ascorbic acid), chelating agents (such as citric acid), organic or inorganic acidifying agents (such as malic acid, acetic acid, citric acid, tartaric acid, phosphoric acid), bitter substances (such as quinine, caffeine, limonin, amygdalin, humulone (humolone), lupulone (lupulone), catechins, tannins), mineral salts (such as sodium chloride, potassium chloride, magnesium chloride, sodium phosphate), substances that prevent enzymatic browning (such as sulfites, ascorbic acid), essential oils, plant extracts, natural or synthetic dyes or colouring pigments (such as carotenoids, flavonoids, anthocyanidins, chlorophylls and derivatives thereof), fragrances, tris (trigemilly) active substances or plant extracts comprising such tris active substances, synthetic, natural or equivalent natural fragrances or odorants, and flavouring agents.

The total amount of the above-mentioned bases, auxiliaries and ingredients used in the products for nutrition, oral care or pleasure (e2) in preferred products according to the invention amounts to 5 to 99.999999 wt.%, preferably 10 to 80 wt.% or 10 to 50 wt.% of the total amount of the product.

The above-described preferred products according to the invention (as mentioned above, preferably as defined above as preferred) may be a wide range of products. Thus, preferred products according to the invention are: perfume extracts, perfumes, shaving lotions, colognes, pre-shave products, spray colognes and perfumed refreshing wipes, and also perfumed acidic, alkaline and neutral cleaning products, such as floor cleaners, window glass cleaners, dishwashing products, bath and hygiene cleaners, scrub creams, solid and liquid toilet cleaners, carpet cleaners in powder and foam form, fabric fresheners, easy-iron products, liquid laundry detergents, powder laundry detergents, laundry pretreatment compositions, such as bleaches, soaking products and detergents, laundry fabric softeners, washing soaps, washing tablets, disinfectants, surface sanitizers, and air fresheners in liquid form, in gel form or applied to solid carriers, aerosols, waxes and polishes, such as furniture polishes, floor waxes, shoe polishes, and personal care products, such as solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving foams, bath oils, oil-in-water, water-in-oil and water-in-oil cosmetic emulsions, such as, for example, skin creams and skin paints, face creams and skin paints, sun creams and sun paints, after-sun creams and after-sun paints, hand creams and hand paints, foot creams and foot paints, depilatory creams and depilatory paints, after-shave creams and after-shave paints, tanning creams and tanning paints, hair care products, such as, for example, hair sprays, hair gels, hair sprays, hair rinses, permanent and semi-permanent hair colorants, hair styling products, such as cold wave permanent wave and hair straightening products, hair setting and styling creams, deodorants and antiperspirants, such as underarm sprays, roll-on deodorants (roll-ons), deodorant sticks (deoscillation creams), deodorant creams (deoscillation creams), cosmetic products, such as, for example, eye shadows, nail varnishes, make-up products, lipsticks, mascaras, and also candles, light oils, incense sticks, insecticides, insect repellants and propellants.

Particularly preferred products according to the invention (as mentioned above, preferably as defined above as preferred) are selected from: shampoos, perfume extracts, perfumes, eau de toilette, shaving lotions, colognes, pre-shave products, spray colognes, perfumed refreshing wipes, acidic cleaning products, alkaline and neutral cleaning products, fabric refreshers, easy-to-iron products, liquid laundry detergents, powder laundry detergents, laundry pre-treatment products, laundry fabric softeners, washing soaps, washing tablets, disinfectants, surface disinfectants, air fresheners, sprays, waxes and polishes, personal care products, hand creams and paints, foot creams and paints, depilatory creams and paints, after-shave creams and paints, sunblack creams and paints, hair care products, deodorants and antiperspirants, decorative cosmetic products, candles, lamp oils, fragrances, insecticides, insect repellents and propellants.

In particular, in combination with the preferred products according to the invention described above, particularly pronounced beneficial secondary qualities have been observed (see above). Thus, the above remarks apply to the compounds according to the invention (as described above, preferably as defined above as preferred), to the mixtures according to the invention (as described above, preferably as defined above as preferred) and to the products according to the invention (as described above, preferably as defined above as preferred).

In a preferred embodiment, the product according to the invention is in microencapsulated, spray-dried form as inclusion complex or extruded product. Such embodiments are preferably suitable for further processing of other perfumed products or for addition to such products.

The above-mentioned microencapsulated form of the product according to the invention can be achieved, for example, by a process known as coacervation (coaservation) using encapsulating materials made of, for example, polyurethanes or soft gelatin. Spray-dried products can be prepared, for example, by: spray-drying emulsions or dispersions (in each case comprising the compounds of the invention), in which case modified starches, proteins, dextrins and vegetable gums can be used as carrier materials. The inclusion complex may be prepared, for example, by introducing a dispersion, preferably comprising a cyclodextrin or urea derivative and a compound of the invention, into a suitable solvent, for example, water. Extruded products may be obtained by melting the compounds of the invention together with a suitable waxy substance and/or by extrusion (optionally in a suitable solvent, preferably isopropanol) with subsequent solidification. In our own studies it has been found that the spray-dried product according to the invention in the form of a product for further processing is particularly suitable for use in the production of other products according to the invention. Spray-dried products of this type comprise preferably from 50 to 95% by weight of a carrier material, more particularly maltodextrin and/or starch, from 5% to 40% of an auxiliary agent, preferably a natural or synthetic polysaccharide and/or vegetable gum, preferably modified starch or gum arabic.

In our own studies it has been found that the properties of the product according to the invention improved in this way can often be further optimized (e.g. with respect to a more specific flavour release) by using appropriate packs of material. Suitable materials that may be used preferably comprise waxy plastics such as, for example, polyvinyl alcohol.

In a particular alternative embodiment, the compounds, mixtures and/or products according to the invention are for example starting from phosphatidylcholine, first incorporated into an emulsion, into liposomes, into microspheres, into nanospheres or else into capsules, granules or extrudates consisting of a matrix suitable for food and pleasure products, for example consisting of starch, starch derivatives (for example modified starch), cellulose or cellulose derivatives (for example hydroxypropylcellulose), other polysaccharides (for example dextrins, alginates, curdlan, carrageenan, chitin, chitosan, pullulan), natural fats, natural waxes, (such as beeswax, carnauba wax) or of proteins such as gelatin, or of other natural products (for example shellac). Depending on the matrix, the products herein may be obtained by spray drying, spray granulation, melt granulation, coacervation, coagulation, extrusion, melt extrusion, emulsion processes, coating or other suitable encapsulation processes and optionally suitable combinations of the foregoing. Particularly preferred matrix materials in respect of the above-mentioned matrices are those which delay the release of the compounds, mixtures or products according to the invention, thus producing a long-lasting effect. Particularly preferred in this connection are fats, waxes, polysaccharides or protein matrices.

In another specific embodiment, the compounds, mixtures and/or products according to the invention are first complexed with one, two or more complexing agents, for example with a cyclodextrin or a cyclodextrin derivative (preferably α -cyclodextrin or β -cyclodextrin), and are used in this complexed form or are further processed.

In a preferred embodiment, the present invention relates to products for oral care, preferably oral care products and/or dental care products, such as toothpastes, tooth gels, tooth powders, mouthwashes and other oral care products.

Dental care products (products for oral care) comprising a compound, mixture or product according to the invention generally comprise, for example: abrasive systems (abrasives or polishes), such as silica, calcium carbonate, calcium phosphate, aluminum oxide and/or hydroxyapatite, for example, surface-active substances, such as sodium lauryl sulfate, sodium lauryl sarcosinate and/or cocamidopropyl betaine, for example, humectants, such as glycerol and/or sorbitol, for example, thickeners, such as carboxymethylcellulose, polyethylene glycol, carrageenan and/or

For example, sweetening agents, such as saccharin, e.g. taste-modifying agents for unpleasant tastes, taste-modifying agents for other, generally unpleasant tastes, taste-regulating substances (e.g. inositol phosphates, nucleotides, such as guanosine monophosphate, adenosine monophosphate or other compounds, such as sodium glutamate or 2-phenoxypropionic acid), active ingredients having a cooling effectSuch as, for example, menthol derivatives (e.g., L-menthol, L-menthyl lactate, L-menthyl carbonate, menthone ketals, menthane carboxamides), 2,2, 2-trialkyl amides (e.g., N-methyl-2, 2-diisopropylpropionamide), 1- (2-hydroxyphenyl) -4- (3-nitrophenyl) -1,2,3, 6-tetrahydropyrimidin-2-one (icilin) and icilin derivatives, stabilizers and active ingredients, such as sodium fluoride, sodium monofluorophosphate, tin difluoride, quaternary ammonium fluorides, zinc citrate, zinc sulfate, tin pyrophosphate, tin dichloride, mixtures of different pyrophosphates, triclosan, cetylpyridinium chloride, aluminum lactate, potassium citrate, potassium nitrate, potassium chloride, strontium chloride, hydrogen peroxide, flavoring agents and/or sodium bicarbonate or flavoring agents.

Another aspect of the invention relates to the use of a compound according to the invention (as described above, preferably as defined above as preferred), the use of a mixture according to the invention (as described above, preferably as defined above as preferred) and the use of a product according to the invention (as described above, preferably as defined above as preferred)

-as odorant or as odorant mixture or as odorant product, preferably with one or more odor notes selected from musk, gloss, gentleness, woody, sexual, floral and delightful, more preferably with musky odor notes

And/or

For replacing musk odorants, musk odorant mixtures or musk odorant products having poor adhesion and/or poor affinity and/or poor biodegradability

And/or

For enhancing and/or modifying the odor profile, preferably one or more odor profiles selected from musk, glossy, soft, woody, sexy, floral and delightful, more preferably with a musk odor profile

And/or

-for providing skin and/or textile fibers having one or more odor profiles selected from musk, shine, softness, woody, sexual, floral and delightful, more preferably having a musk odor profile

And/or

-as an agent for increasing the substantivity and/or retention of an odorant mixture and/or as an immobilizing agent and/or agent for enhancing the odor of other odorants perceived by an aqueous solution comprising a surfactant.

In our own studies, it has been found that the use according to the invention of the compounds according to the invention, of the mixtures according to the invention and of the products according to the invention, each as described above, preferably as defined above, being preferred, leads in many cases to a very beneficial effect on the (above) secondary properties. The remarks above apply accordingly. Their use has been found to result in the beneficial modulation of one, two, three or more or all of the following odor profiles: musk, glossy, soft, aucklandia root, sexy, floral and delightful, musk is preferred.

The above remarks about the compounds according to the invention, the mixtures according to the invention and the products according to the invention, each as described above, preferably as defined above as preferred, also apply to the uses according to the invention.

In our own studies it has often been found that the compounds according to the invention and/or the mixtures according to the invention are particularly suitable as so-called potentiators. These synergists are preferably used in the form of the mixtures according to the invention (the remarks made above regarding the compounds according to the invention, the mixtures according to the invention and the products according to the invention apply).

The term "textile fibers" encompasses all fibers useful for processing textiles. They share the characteristic of also comprising a long length compared to their cross section and also of sufficient strength and flexibility. The term "textile fibre" especially relates to natural fibres (such as, for example, hair) and artificial fibres.

For the terms affinity, adhesion and retention see the comments above in the previous section. Wherein the above-mentioned use according to the invention involves replacing a musk odorant, a musk odorant mixture or a musk odorant product, respectively non-inventive compounds, mixtures or products, having a lower adhesion and/or a lower affinity and/or a lower biodegradability, but which all impart a musk odor note. For non-inventive compounds present in the non-inventive mixture and/or product, see the earlier section above.

The use according to the invention (as described above) generally results in beneficial fixative properties-that is, the compounds of the invention are generally used as fixatives. As a fixative, the compounds of the present invention (as described above, preferably as defined above as preferred) either increase the adhesion strength of other odorants by reducing the pressure of the vapor or enhancing its odor (e.g., lowering the threshold). The invention therefore also relates to the use of the compounds and/or mixtures and products according to the invention as fixatives.

A further aspect of the invention relates to a method for imparting an odour with one, two or more or all of the following odour notes: musk, glossy, soft, aucklandia root, sexy, flowery scent and delightful; or for enhancing an odor having one, two or more or all of the following odor tonality: woody, floral, fresh, green, fruity, musk and spicy; the method comprises the following steps:

producing or providing one or more products not including a compound of the invention

Or

Providing human or animal skin or human or animal hair,

(ii) production or provision of

The compounds of the invention (as described above, preferably as defined above as preferred),

or

The mixture according to the invention (as described above, preferably as defined above as preferred),

or

A product according to the invention (as described above, preferably as defined above as preferred),

(iii) mixing or contacting the articles produced or provided in steps (i) and (ii), i.e. the product produced or provided in step (i) and/or the skin of a human or animal and/or the hair of a human or animal and the product according to the invention or the mixture according to the invention or the compound according to the invention produced or provided in step (ii),

wherein the amount of the article used in step (iii) produced in step (ii) is sufficient to impart one, two or more or all of the following odor notes: musk, glossy, soft, aucklandia root, sexy, flowery scent and delightful; and/or sufficient to enhance one, two or more or all of the following odor notes: woody, floral, fresh, green, fruity, musk and spicy.

A further aspect of the invention relates to a process for the production of a compound of formula (Ia) or a compound of formula (Ib), the process comprising the steps of:

-producing or providing a compound of formula (IV),

wherein X is methylene or ethylene

-reacting the compound of formula (IV) in one or more steps to obtain the compound of formula (Ia) and/or the compound of formula (Ib).

The preparation of the compounds of the invention can be carried out by reactions and methods known per se.

For example, cyclododecanone can be reacted with propenyl acetate to give the compound of formula (II) and subsequently, the inventive compound of formula (Ia) or (Ib) (X ═ methylene) (see formula I and examples in the later section below).

The formula scheme I is as follows:

in a process based on the teaching of DE3137939A1, cyclododecanone can be converted into compounds of the formula (III). Starting from the compound of formula (III), this compound can be reacted in a further reaction step to give the inventive compound of formula (Ia) or compound of formula (Ib), wherein X ═ methylene (see formula II and examples in the later section below).

The formula scheme II comprises the following steps:

in an alternative reaction step, starting from a compound of formula (III), the compound may also be reacted to form the inventive compound of formula (Ia) or compound of formula (Ib), wherein X ═ methylene (see formula III):

the formula scheme is three:

the person skilled in the art is aware of suitable techniques and methods for enabling the inventive compounds of formula (Ia) or compounds of formula (Ib) to be separated from one another if they are present in the reaction mixture after synthesis (possibly also at different concentrations). Such suitable methods and techniques include conventional separation methods, preferably HPLC and/or PCG methods using suitable process conditions.

A further aspect of the invention relates to the use of compounds of formula (IV)

Wherein X is a methylene or ethylene group

Said compound of formula (IV) is useful as an intermediate in the preparation of the inventive compound of formula (Ia) or of the inventive compound of formula (Ib).

The following examples provide illustrative illustrations of the present invention without limiting the subject matter of the invention to these examples. All data, particularly the percent (%) data, are by weight unless otherwise indicated.