Water-soluble composition, preparation method and application thereof
阅读说明：本技术 水溶性组合物及其制备方法与应用 (Water-soluble composition, preparation method and application thereof ) 是由 张兵 张炽坚 伍宇飞 何廷刚 胡丽云 艾勇 张文环 屈恋 克里斯特勒热夫雷 弗兰克 于 2019-09-20 设计创作，主要内容包括：本发明涉及厚朴总酚衍生物领域,公开了一种水溶性组合物,该水溶性组合物由具有式(1)和式(2)结构的化合物组成。本发明制备的厚朴总酚衍生物具有良好水溶性,溶解后无色透明,对常见的革兰氏阴性菌、革兰氏阳性菌、真菌等具有显著的抑制效果,可作为绿色天然的防腐剂应用于食品、药品及化妆品等领域。<Image he="1000" wi="624" file="DDA0002209728330000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>(The invention relates to the field of magnolia officinalis total phenol derivatives, and discloses a water-soluble composition which is composed of compounds with structures of a formula (1) and a formula (2). The magnolia total phenol derivative prepared by the invention has good water solubility, is colorless and transparent after being dissolved, has obvious inhibition effect on common gram-negative bacteria, gram-positive bacteria, fungi and the like, and can be used as a green natural preservative to be applied to the fields of food, medicines, cosmetics and the like.)
1. A water-soluble composition consisting of a compound having the structure of formula (1) and a compound having the structure of formula (2):
wherein the content of the compound with the structure of the formula (1) in the water-soluble composition is 20-80 wt%;
in the formulae (1) and (2), R1、R2、R3And R4Each independently selected from hydrogen, halogen, substituted or unsubstituted C1-C10Alkyl, substituted or unsubstituted C1-C12Alkoxy, substituted or unsubstituted C6-C10Aryl of (a);
R1、R2、R3and R4Each of the substituents optionally present on (A) is independently selected from halogen, C1-C6Alkoxy and C6-C10Aryl of (a);
R1、R2、R3and R4Each independently is substituted or unsubstituted C1-C10Alkyl groups of (a);
R1、R2、R3and R4Each of the substituents optionally present on (A) is independently selected from hydroxy, carboxy, C1-C6Alkoxy of the general formula-O-R9-a group of OH structure;
wherein R is9Is C1-C6An alkylene group of (a);
R5、R6、R7and R8Each independently selected from hydrogen and C6-C10Aryl and C1-C6Alkyl group of (1).
2. The water-soluble composition of claim 1, which isIn the formulae (1) and (2), R1、R2、R3And R4Each independently selected from hydrogen, fluorine, chlorine, bromine, substituted or unsubstituted C1-C5Alkyl, substituted or unsubstituted C1-C6Alkoxy, substituted or unsubstituted C6-C8Aryl of (a);
R1、R2、R3and R4Each of the substituents optionally present on (A) is independently selected from fluorine, chlorine, bromine, C1-C3Alkoxy and C6-C8Aryl of (a);
R1、R2、R3and R4Each independently is substituted or unsubstituted C1-C5Alkyl groups of (a);
R1、R2、R3and R4Each of the substituents optionally present on (A) is independently selected from hydroxy, carboxy, C1-C3Alkoxy of the general formula-O-R9-a group of OH structure;
wherein R is9Is C1-C3An alkylene group of (a);
R5、R6、R7and R8Each independently selected from hydrogen and C6-C8Aryl and C1-C3Alkyl groups of (a);
preferably, in formula (1) and formula (2), R5、R6、R7And R8Are all hydrogen.
3. The water-soluble composition according to claim 1 or 2, wherein the compound having the structure of formula (1) is selected from at least one of the following compounds:
compound 1:
compound 2:
compound 3:
compound 4:
compound 5:
wherein the compound with the structure of the formula (2) is selected from at least one of the following compounds:
compound 6:
compound 7:
compound 8:
compound 9:
compound 10:
4. a method for preparing a water-soluble composition, which is characterized by comprising the steps of carrying out first contact on a compound with a structure shown in a formula (3) and/or a formula (4) and a compound with a structure shown in a formula (5) and/or a formula (6) under Mannich reaction conditions, and then carrying out second contact on a product obtained by the first contact and a composition consisting of the compound with a structure shown in a formula (7) and the compound with a structure shown in a formula (8) to obtain a Mannich reaction product;
wherein the content of the compound represented by the formula (7) and the content of the compound represented by the formula (8) in the composition are not zero;
R1、R2、R3and R4Each independently is substituted or unsubstituted C1-C10Alkyl groups of (a);
R1、R2、R3and R4Each of the substituents optionally present on (A) is independently selected from hydroxy, carboxy, C1-C6Alkoxy of the general formula-O-R9-a group of OH structure;
wherein R is9Is C1-C6An alkylene group of (a);
R5、R6、R7and R8Each independently selected from hydrogen and C6-C10Aryl and C1-C6Alkyl groups of (a);
in the formulae (7) and (8), R1、R2、R3And R4Each independently selected from hydrogen, halogen, substituted or unsubstituted C1-C10Alkyl, substituted or unsubstituted C1-C12Alkoxy, substituted or unsubstituted C6-C10Aryl of (a);
R1、R2、R3and R4Each of the substituents optionally present on (A) is independently selected from halogen, C1-C6Alkoxy and C6-C10Aryl group of (1).
5. The method according to claim 4, wherein the compound having the structure of formula (3) and/or formula (5) is selected from at least one of N-methyl-glycine, N-ethyl-glycine, N-methyl-aminoethoxyethanol, N-ethyl-aminoethoxyethanol, methylaminoacetaldehyde dimethyl acetal, methylaminoacetaldehyde diethyl acetal, ethylaminoacetaldehyde dimethyl acetal, diethanolamine, dimethylamine, diethylamine, di-N-propylamine;
the molar ratio of the total amount of the compound having the structure of formula (3) and/or formula (5), the total amount of the compound having the structure of formula (4) and/or formula (6) to the composition consisting of the compounds having the structures of formula (7) and formula (8) is 0.5 to 6: 0.5-6: 1, preferably 1 to 4: 1-4: 1.
6. the method according to claim 4, wherein the compound having the structure of formula (4) and/or formula (6) is at least one selected from formaldehyde, acetaldehyde, propionaldehyde, benzaldehyde, phenylacetaldehyde, o-methyl benzaldehyde, and preferably formaldehyde.
7. The method of claim 4, wherein the first and second contacting are both performed in the presence of water and/or an organic solvent, and in acidic conditions provided by at least one of hydrochloric acid, phosphoric acid, sulfuric acid, and acetic acid;
preferably, the organic solvent is selected from at least one of methanol, ethanol and acetic acid, preferably methanol and/or ethanol.
8. The method of claim 7, wherein the first contacting comprises adding the compound having the structure of formula (4) and/or formula (6) to the compound having the structure of formula (3) and/or formula (5) at 20-50 ℃, then adding the acidic substance or the solution of the acidic substance in the solvent at 1-10 ℃, and continuing the reaction for 0.5-2 h;
preferably, the second contacting mode comprises dissolving the compounds with the structures of the formula (7) and the formula (8) in the solvent in the presence of an acidic substance to form a solution, and then carrying out the second contacting with the product obtained by the first contacting.
9. Use of a water-soluble composition according to any one of claims 1 to 3 for bacteriostasis.
10. The use according to claim 9, wherein the bacteria are selected from at least one of escherichia coli, staphylococcus aureus, pseudomonas aeruginosa, candida albicans, aspergillus niger; preferably, the bacteria are present in the food, pharmaceutical or cosmetic product in an amount of 0.001-0.01 gram per gram of the food, pharmaceutical or cosmetic product.
Technical Field
The invention relates to the field of magnolia officinalis total phenol derivatives, in particular to a composition of magnolia officinalis total phenol derivatives and a preparation method and application thereof.
Background
The food, the medicine and the cosmetics are rich in a large amount of water and various nutritional ingredients, a good growth environment is provided for microorganisms, and the microorganisms are difficult to invade in the production and use processes of the cosmetics, so that the cosmetics are extremely easy to decay, the quality of the products is reduced, and the health of users is threatened. The addition of the preservative into the cosmetics is an important means for protecting the products from microbial contamination, prolonging the shelf life of the products and ensuring the safety of the products.
Currently, many kinds of preservatives are used in foods, medicines and cosmetics, most of them are chemical preservatives, and dozens of them are commonly used, including acidic preservatives (benzoic acid), ester-type preservatives (parabens) and the like. However, with the development of science and the increasing awareness of safety of consumers, it is gradually found that although chemical preservatives have a good antiseptic effect, some chemical preservatives can produce adverse effects on human bodies, cause skin allergy, decrease physical functions and pollute the environment. Therefore, natural preservatives are urgently needed by various industries, and a natural preservative with low toxicity, low irritation and high performance has great significance in the fields of food, medicines, cosmetics and the like.
Cortex magnoliae officinalis (Magnolia officinalis cortex) is dried bark, root bark and branch of Magnolia officinalis linasl srehd.et wils, belonging to important traditional Chinese medicinal materials and being listed as a high-quality product in the Shennong Ben Cao Jing. Cortex Magnolia officinalis is bitter and pungent, warm in nature, and has effects in promoting qi circulation, eliminating dampness, warming middle warmer, relieving pain, lowering adverse qi, and relieving asthma. The main chemical active ingredients of the magnolia officinalis are lignans, magnolol, honokiol and the like. The phenols in cortex Magnolia officinalis have antibacterial, antitumor, analgesic, and antiinflammatory effects. But because the water solubility is poor, the mangnolia officinalis total phenols are easy to oxidize and deteriorate, and the application of the mangnolia officinalis total phenols in foods, medicines and cosmetics is greatly hindered. Generally, the general surfactants and emulsifiers can be used for solubilizing the total magnolol, in this case, the dosage of the required surfactants and emulsifiers is very large, and even if the total magnolol is applied to an aqueous formula, the total magnolol can be separated out from the aqueous formula, so that the whole system becomes white and turbid, and the use is seriously influenced. In addition, a small amount of alkali can be added into the formula system to convert the total phenols of the magnolia officinalis into salts and increase the water solubility of the total phenols of the magnolia officinalis, and the total phenols of the magnolia officinalis formed by the method are extremely unstable and easily become golden yellow, so that the conductivity of the system is increased and the bacteriostatic ability is reduced. The above method has very high requirements on the pH of a product formula system and the dosage accuracy of a thickener and an emulsifier, so that the method is basically difficult to process and apply.
The traditional method for improving the solubility of the total phenols of magnolia officinalis introduces impurity compounds into a protogen system, and the thick total phenols of magnolia officinalis are unstable after being dissolved in an aqueous solution system, so that the system is easy to deteriorate, and the bacteriostatic ability is reduced. Therefore, the modification of the structure of the total phenols of the magnolia officinalis improves the solubility and the bacteriostatic ability of the total phenols of the magnolia officinalis in water, and is a problem to be solved urgently when the total phenols of the magnolia officinalis are used as natural preservatives to be applied to foods, medicines and cosmetics.
Disclosure of Invention
The invention aims to solve the problems of poor water solubility of the total phenols of magnolia officinalis and reduced bacteriostatic ability after the total phenols of magnolia officinalis are dissolved in an aqueous solution system, and provides a composition of the total phenols of magnolia officinalis and a preparation method and application thereof. The water-soluble magnolia total phenol derivative provided by the invention has excellent stability and bacteriostatic ability when being applied to a preservative.
In order to achieve the above object, in a first aspect, the present invention provides a water-soluble composition consisting of a compound having a structure of formula (1) and a compound having a structure of formula (2):
wherein the content of the compound with the structure of the formula (1) in the water-soluble composition is 20-80 wt%.
According to the invention, in the formulae (1) and (2), R1、R2、R3And R4Each independently selected from hydrogen, halogen, substituted or unsubstituted C1-C10Alkyl, substituted or unsubstituted C1-C12Alkoxy, substituted or unsubstituted C6-C10Aryl group of (1).
Preferably, R1、R2、R3And R4Each of the substituents optionally present on (A) is independently selected from halogen, C1-C6Alkoxy and C6-C10Aryl group of (1).
Preferably, R1、R2、R3And R4Each independently is substituted or unsubstituted C1-C10Alkyl group of (1).
Preferably, R1、R2、R3And R4Each of the substituents optionally present on (A) is independently selected from hydroxy, carboxy, C1-C6Alkoxy of the general formula-O-R9-a radical of the OH structure.
Wherein R is9Is C1-C6An alkylene group of (a).
Preferably, R5、R6、R7And R8Each independently selected from hydrogen and C6-C10Aryl and C1-C6Alkyl group of (1).
In a second aspect, the present invention provides a method for preparing a water-soluble composition, which comprises first contacting a compound having a structure of formula (3) and/or (4) with a compound having a structure of formula (5) and/or (6) under Mannich reaction conditions, and then second contacting the product of the first contacting with a composition consisting of a compound having a structure of formula (7) and a compound having a structure of formula (8) to obtain a Mannich reaction product.
Wherein the content of the compound with the structure of the formula (1) in the water-soluble composition is 20-80 wt%.
Preferably, in formula (3) and formula (5), R1、R2、R3And R4Each independently is substituted or unsubstituted C1-C10Alkyl group of (1).
Preferably, R1、R2、R3And R4Each of the substituents optionally present on (A) is independently selected from hydroxy, carboxy, C1-C6Alkoxy of the general formula-O-R9-a radical of the OH structure.
Wherein R is9Is C1-C6An alkylene group of (a).
Preferably, in formula (4) and formula (6), R5、R6、R7And R8Each independently selected from hydrogen and C6-C10Aryl and C1-C6Alkyl group of (1).
Preferably, in formula (7) and formula (8), R1、R2、R3And R4Each independently selected from hydrogen, halogen, substituted or unsubstituted C1-C10Alkyl, substituted or unsubstituted C1-C12Alkoxy, substituted or unsubstituted C6-C10Aryl group of (1).
Preferably, R1、R2、R3And R4Optionally toThe substituents present are each independently selected from halogen, C1-C6Alkoxy and C6-C10Aryl group of (1).
In a third aspect, the invention provides the use of the water-soluble composition in bacteriostasis.
The modified magnolia officinalis total phenol derivative which can be used for bacteriostasis is prepared by modifying the structure of the magnolia officinalis total phenol, has good water solubility, is colorless and transparent after being dissolved, has obvious inhibition effect on common gram-negative bacteria, gram-positive bacteria, fungi and the like, and can be used as a green and natural preservative to be applied to the fields of food, medicines, cosmetics and the like.
Additional features and advantages of the invention will be set forth in the detailed description which follows.
Detailed Description
The following is a detailed description of specific embodiments of the present invention. It should be understood that the detailed description and specific examples, while indicating the present invention, are given by way of illustration and explanation only, not limitation.
The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and such ranges or values should be understood to encompass values close to those ranges or values. For ranges of values, between the endpoints of each of the ranges and the individual points, and between the individual points may be combined with each other to give one or more new ranges of values, and these ranges of values should be considered as specifically disclosed herein.
Some of the terms referred to in this aspect are explained below:
“C1-C10the "alkyl group" of (a) represents an alkyl group having 1 to 10 carbon atoms in total, and includes a straight-chain alkyl group, a branched-chain alkyl group or a cyclic alkyl group, and specifically may be a straight-chain alkyl group, a branched-chain alkyl group or a cyclic alkyl group having 1, 2,3, 4, 5, 6, 7, 8, 9, 10 carbon atoms in total, and may be, for example, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, a n-pentyl group, an isopentyl group, a n-hexyl group, a,Methylcyclopropyl, ethylcyclopropyl, cyclopentyl, methylcyclopentyl, cyclohexyl, and the like.
“C1-C12The "alkoxy group" of (b) represents an alkoxy group having 1 to 12 carbon atoms in total, and includes a linear alkoxy group, a branched alkoxy group and a cycloalkoxy group, and specifically may be a linear alkoxy group, a branched alkoxy group or a cycloalkoxy group having 1, 2,3, 4, 5, 6, 7, 8, 9, 10, 11, 12 carbon atoms in total, and may be, for example, a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, an isobutoxy group, a t-butoxy group, a n-pentoxy group, an isopentoxy group, a n-hexoxy group, a n-heptoxy group, a n-octoxy group, a n-nonoxy group, a n-decoxy group, a cyclopropoxy group, a methyl cyclopropoxy.
“C6-C10The "aryl group" of (a) represents an aryl group having 6 to 10 carbon atoms in total, at least one H group being substituted by C on the benzene ring of the aryl group1-C4And alkyl group of (a) is substituted, for example, tolyl, ethylphenyl, n-propylphenyl, isopropylphenyl, n-butylphenyl, orthoxylyl, m-xylyl, p-xylyl, etc.
Other similar groups are defined herein with reference to the foregoing definitions, only with respect to the number of carbon atoms or the manner of isomerisation.
In a first aspect, the present invention provides a water-soluble composition consisting of a compound having the structure of formula (1) and a compound having the structure of formula (2):
wherein the content of the compound with the structure of the formula (1) in the water-soluble composition is 20-80 wt%.
Preferably, in formula (1) and formula (2), R1、R2、R3And R4Each independently selected from hydrogen, halogen, substituted or unsubstituted C1-C10Alkyl, substituted or unsubstituted C1-C12Alkoxy, substituted or unsubstituted C6-C10Aryl group of (1).
Preferably, R1、R2、R3And R4Each of the substituents optionally present on (A) is independently selected from halogen, C1-C6Alkoxy and C6-C10Aryl group of (1).
Preferably, R1、R2、R3And R4Each independently is substituted or unsubstituted C1-C10Alkyl group of (1).
Preferably, R1、R2、R3And R4Each of the substituents optionally present on (A) is independently selected from hydroxy, carboxy, C1-C6Alkoxy of the general formula-O-R9-a radical of the OH structure.
Wherein R is9Is C1-C6An alkylene group of (a).
Preferably, R5、R6、R7And R8Each independently selected from hydrogen and C6-C10Aryl and C1-C6Alkyl group of (1).
According to a preferred embodiment of the present invention, wherein, in the formulae (1) and (2), R1、R2、R3And R4Each independently selected from hydrogen, fluorine, chlorine, bromine, substituted or unsubstituted C1-C5Alkyl, substituted or unsubstituted C1-C6Alkoxy, substituted or unsubstituted C6-C8Aryl group of (1).
Preferably, R1、R2、R3And R4Each of the substituents optionally present on (A) is independently selected from fluorine, chlorine, bromine, C1-C3Alkoxy and C6-C8Aryl group of (1).
R1、R2、R3And R4Each independently is substituted or unsubstituted C1-C5Alkyl group of (1).
R1、R2、R3And R4Each of the substituents optionally present on (A) is independently selected from hydroxy, carboxy, C1-C3Alkoxy group of,The general formula is-O-R9-a radical of the OH structure.
Wherein R is9Is C1-C3An alkylene group of (a).
Preferably, R1、R2、R3And R4Each independently of the other being methyl,
R5、R6、R7And R8Each independently selected from hydrogen and C6-C8Aryl and C1-C3Alkyl groups of (a);
preferably, in formula (1) and formula (2), R5、R6、R7And R8Are all hydrogen.
According to a preferred embodiment of the present invention, in the water-soluble composition, the compound having the structure of formula (1) is selected from at least one of the following compounds:
compound 1:
compound 2:
compound 3:
compound 4:
compound 5:
wherein the compound with the structure of the formula (2) is selected from at least one of the following compounds:
compound 6:
compound 7:
compound 8:
compound 9:
compound 10:
the inventor of the invention finds that the composition of the magnolia total phenol derivative in the preferred embodiment has more excellent water solubility and bacteriostatic ability.
In a second aspect, the present invention provides a method for preparing a water-soluble composition, which comprises first contacting a compound having a structure of formula (3) and/or (4) with a compound having a structure of formula (5) and/or (6) under Mannich reaction conditions, and then second contacting the product of the first contacting with a composition consisting of a compound having a structure of formula (7) and a compound having a structure of formula (8) to obtain a Mannich reaction product.
Wherein the content of the compound with the structure of the formula (1) in the water-soluble composition is 20-80 wt%.
Preferably, in formula (3) and formula (5), R1、R2、R3And R4Each independently is substituted or unsubstituted C1-C10Alkyl group of (1).
R1、R2、R3And R4Each of the substituents optionally present on (A) is independently selected from hydroxy, carboxy, C1-C6Alkoxy of the general formula-O-R9-a radical of the OH structure.
Wherein R is9Is C1-C6An alkylene group of (a).
Preferably, in formula (4) and formula (6), R5、R6、R7And R8Each independently selected from hydrogen and C6-C10Aryl and C1-C6Alkyl group of (1).
Preferably, in formula (7) and formula (8), R1、R2、R3And R4Each independently selected from hydrogen, halogen, substituted or unsubstituted C1-C10Alkyl, substituted or unsubstituted C1-C12Alkoxy, substituted or unsubstituted C6-C10Aryl group of (1).
R1、R2、R3And R4Each of the substituents optionally present on (A) is independently selected from halogen, C1-C6Alkoxy and C6-C10Aryl group of (1).
According to the present invention, the compound having the structure of formula (3) and/or formula (5) is an amine compound, and the amine is not particularly limited in the present invention, and may be a linear alkylamine, a branched alkylamine, a cycloalkylamine, a hydroxyalkylamine, or various amino acids, and preferably a secondary amine thereof, and the secondary amine is not particularly limited in the present invention, and preferably is at least one of N-methyl-glycine, N-ethyl-glycine, N-methyl-aminoethoxyethanol, N-ethyl-aminoethoxyethanol, methylaminoacetaldehyde dimethyl acetal, methylaminoacetaldehyde diethyl acetal, ethylaminoacetaldehyde dimethyl acetal, diethanolamine, dimethylamine, diethylamine, and di-N-propylamine.
Preferably, the molar ratio of the total amount of the compound having the structure of formula (2) and/or formula (4), the total amount of the compound having the structure of formula (4) and/or formula (6), and the composition consisting of the compounds having the structures of formula (7) and formula (8) is 0.5 to 6: 0.5-6: 1, preferably 1 to 4: 1-4: 1.
preferably, the compound having the structure of formula (4) and/or formula (6) is an aldehyde compound, and the aldehyde compound is not particularly limited in the present invention, and for example, the aldehyde selected may be at least one of formaldehyde, acetaldehyde, propionaldehyde, and benzaldehyde, and is preferably formaldehyde.
According to a preferred embodiment of the present invention, the first and second contacting are carried out in the presence of an acidic substance and a solvent, wherein the solvent is water and/or an organic solvent. The acidic substance is not particularly limited, and may be at least one of hydrochloric acid, sulfuric acid, phosphoric acid, or acetic acid.
According to a preferred embodiment of the present invention, the first and second contacting are carried out in the presence of water and/or an organic solvent, which is not particularly limited in the present invention and may be conventionally selected in the art, preferably a polar organic solvent, further preferably a polar solvent containing a hydroxyl group or a carbonyl group, for example, the organic solvent is preferably selected from methanol, ethanol and acetic acid, preferably methanol and/or ethanol.
According to a preferred embodiment of the present invention, the method for preparing the composition of the magnolia total phenol derivative comprises the steps of mixing the compound having the structure of formula (3) and/or formula (5) with the compound having the structure of formula (4) and/or formula (6) under Mannich reaction conditions for first contact, and then carrying out second contact on the product obtained by the first contact and the composition of the compound having the structure of formula (7) and the compound having the structure of formula (8). In the first contact, the aldehyde compound is first contacted with the secondary amine compound at a temperature of 20 to 50 deg.C, preferably 30 to 40 deg.C, for 5 to 20min, preferably 10 to 15 min. The aldehyde compound may be in the form of a solution, and the solvent of the solution is water. Subsequently, the first contacted system is placed in a low-temperature water bath, the acidic substance or the solution of the acidic substance in the organic solvent is added into the system, the temperature is controlled to be 1-10 ℃, preferably 2-5 ℃, and the continuous contact time is 0.5-2h, preferably 0.6-1.5 h. In the present invention, the timing of adding the acidic substance is not particularly limited, and the acid may be added at the same time as the first contact, and preferably, the acid is added to the organic solvent first and then added together with the organic solvent. The inventors of the present invention have found that the above preferred mode is effective in reducing acid mist and avoiding the side reaction due to the exothermic heat of reaction, as compared with the mode in which the acid is directly added to the reactants. The low-temperature water bath is not particularly limited, and may be selected conventionally in the field, and is preferably an ice salt bath, and the salt in the ice salt bath is not particularly limited, and is preferably at least one of potassium chloride, sodium sulfate, and potassium sulfate. In the ice salt bath, the amount of the salt is 0.5 to 5 wt% based on the weight of water.
Preferably, the second contacting is carried out at a temperature of from 30 to 90 deg.C, preferably from 70 to 85 deg.C, for a period of from 1 to 3 hours, preferably from 1.5 to 2 hours.
According to the present invention, preferably, the method further comprises: the product of the second contact of step (ii) is evaporated and purified in sequence. The evaporation operation is not particularly limited in the invention and can be selected conventionally in the field, and the invention adopts a rotary evaporator to evaporate and remove most of the organic solvent; the purification operation is not particularly limited in the present invention, and may be a conventional operation in the field, preferably purification is performed by column chromatography, the purification packing is 100-200 mesh silica gel, the eluent is not particularly limited and may be a conventional choice in the field, preferably, the eluent is ethyl acetate/acetone, and the volume ratio of ethyl acetate and acetone is preferably 2-6:1, and particularly preferably 4: 1.
According to the invention, preferably, the compound with the structure of the formula (7) and the compound with the structure of the formula (8) are both from plant extracts, the plant in the invention is magnolia officinalis belonging to magnoliaceae, and the content of the composition of the compound with the structure of the formula (7) and the compound with the structure of the formula (8) in the extracts is more than or equal to 80%.
In a third aspect, the invention also provides an application of the water-soluble composition in bacteriostasis.
The magnolia total phenol derivative provided by the invention can be applied to food, medicine and cosmetics, can be used as a preservative or a preservative component, and has an inhibiting effect on common escherichia coli, staphylococcus aureus, pseudomonas aeruginosa, candida albicans, aspergillus niger and the like. The total phenol derivative of Magnolia officinalis is used in an amount of 0.001-0.01 g per gram of the food, medicine or cosmetic.
The present invention will be described in detail below by way of examples. In the following examples, the molecular structure of the prepared magnolia total phenol derivative is measured by a flight time mass spectrometer, a nuclear magnetic resonance spectrometer and a liquid chromatography mass spectrometer, wherein the flight mass spectrometer is of the type HR EI-TOFMS and is purchased from Kore company in UK; the model of the nmr spectrometer was semer femospin 80, purchased from semer femtole corporation; the model of the liquid chromatography-mass spectrometer is a TSQ Altis triple quadrupole mass spectrometer purchased from Saimer Fei company; the content of the plant-derived magnolia officinalis total phenols is 70%, 80% and 90%, and the magnolia officinalis total phenols are purchased from Hainan Jiamu Biotechnology limited; the N-methyl-glycine powder and N-methyl-aminoglyoxal dimethyl acetal are purchased from Shanghai Merlin biological reagents, Inc.; the nutrient broth is purchased from Beijing Meiruida science and technology Limited and mainly comprises peptone, beef extract, sodium chloride and water; the Sa's medium is purchased from Shandong West Asia chemical industry Co., Ltd, and contains peptone and agar as main ingredients; TTC is short for 2,3, 5-triphenyltetrazolium chloride, and the used TTC reagent is purchased from Shanghai leaf Biotech limited; nipagin methyl ester is analytically pure and purchased from Shanghai Michelin Biochemical technology, Inc.; phenoxyethanol was analytically pure and purchased from Shanghai Aladdin Biotechnology GmbH.
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