阅读说明：本技术 用于烟草加香的释放型木糖酯香料合成方法 (Synthesis method of release type xylose ester perfume for perfuming tobacco ) 是由 张凤侠 彭军仓 师金鸽 杨芳 何媛 张萌萌 吕娟 康世平 王瑶 赵敏 孙赵麟 于 2019-11-12 设计创作，主要内容包括：提供一种用于烟草加香的释放型木糖酯香料合成方法,以葡萄糖为原料,采用羧酸与醇酯化做酯的原理,通过得到的可以与多种醇类化合物酯化反应的共用母体羧酸(参见产物6)：(3aR,5S,6S,6aR)-6-(苄氧基)-2,2-二甲基四氢呋喃[2,3-d][1,3]二氧戊环-5-羧酸；从而与多种醇类化合合成更优质更广泛的木糖酯(参见产物8)：(1R,2S,5R)-2-异丙基-5-甲基环己基-(3aR,5S,6R,6aR)-6-(羟基)-2,2-二甲基四氢呋喃[2,3-d][1,3]二氧戊环-5-羧酸酯,用于烟草的释放型香料加香生产,进而提高卷烟烟气香气质和香气量,可满足国产释放型烟用香料的自生产添加需求,赋予卷烟烟气异戊酸、乙基月桂烯、4-甲基苯酚等的香气特征,使卷烟烟气更加柔和细腻,谐调性增加,余味变得纯净。(Provides a synthesis method of a release type xylose ester spice for flavoring tobacco, which takes glucose as a raw material, adopts the principle of esterification of carboxylic acid and alcohol to prepare ester, and obtains a common parent carboxylic acid capable of being esterified with various alcohol compounds (see a product 6): (3aR,5S, 6aR) -6- (benzyloxy) -2, 2-dimethyltetrahydrofuran [2,3-d ] [1,3] dioxolane-5-carboxylic acid; thus, the synthesis of the xylose ester with better quality and wider scope by combining with various alcohols (see a product 8): the (1R,2S,5R) -2-isopropyl-5-methylcyclohexyl- (3aR,5S,6R,6aR) -6- (hydroxy) -2, 2-dimethyltetrahydrofuran [2,3-d ] [1,3] dioxolane-5-carboxylic ester is used for the perfuming production of release type perfumes of tobaccos, so that the fragrance quality and the fragrance quantity of cigarette smoke are improved, the self-production addition requirements of the release type perfume for tobaccos in China can be met, the fragrance characteristics of isovaleric acid, ethyl myrcene, 4-methylphenol and the like in the cigarette smoke are endowed, the cigarette smoke is softer and finer, the harmonicity is increased, and the aftertaste is purified.)

1. The synthesis method of the release type xylose ester spice for flavoring the tobacco is characterized by comprising the following steps of: the method comprises the following steps:

step 1: 15-20 g (D +) g of glucose, 150-200 mL of anhydrous acetone and 1.25-1.82 g of anhydrous copper sulfate (CuSO)₄) 0.75-2.25 g of concentrated sulfuric acid (H)₂SO₄) Is arranged atStirring for 48h in a 500mL single-neck flask at room temperature, concentrating in vacuum, and adding 80-120 mL of saturated sodium bicarbonate (NaHCO) into the obtained crude oil₃) Washing, extraction 2 times with 50-95 mL ethyl acetate (EtOAc), combining the organic phases and adding anhydrous sodium sulfate (Na)₂SO₄) Drying and finally vacuum concentrating to obtain 18.95-28 g of white solid product 2: (3aR,5S,6S,6aR) -5- ((S) -2, 2-dimethyl-1, 3-dioxolan-4-yl) -2, 2-dimethyltetrahydrofuran [2,3-d ]][1,3]Dioxolan-6-ol; and the yield of product 2 is 95.3%;

step 2: putting 3.5-7.2 g of the product 2 and 40-70 mL of anhydrous N, N-Dimethylformamide (DMF) into a 200-300 mL four-neck flask, uniformly stirring, and introducing nitrogen for protection; cooling to 0 ℃ in an ice bath, adding 0.85-1 g (24mmol) of 60% sodium hydride (NaH) into the solution in batches, and continuing stirring for 15-20 minutes at the temperature of 0 ℃ while generating bubbles; then slowly dropwise adding 2.8-4.05 g (20mmol) of benzyl bromide (BnBr) into the reaction bottle, and continuously stirring for 2 hours at the room temperature of 20-25 ℃ until the reaction is finished: the reaction solution after the completion of the reaction was extracted with ethyl acetate several times, and then anhydrous sodium sulfate (Na) was added₂SO₄) Drying and elution with 1:4 ethyl acetate (EtOAc) and Petroleum Ether (PE) afforded 5.25-8.2 g of product 3: (3aR,5R,6S,6aR) -6- (benzyloxy) -5- ((S) -2, 2-dimethyl-1, 3-dioxolan-4-yl) -2, 2-dimethyltetrahydrofuran [2,3-d ]][1,3]A dioxolane;

and step 3: placing 5.25-8.2 g of the product 3 and 95% of 50-90 mL of acetic acid (AcOH) aqueous solution in a 250mL single-neck flask, and stirring at room temperature for 24 hours; after vacuum concentration, washing extraction and drying, 3.1-7.2 g of a product 4 is obtained: (S) -1- ((3aR,5R,6S,6aR) -6- (benzyloxy) -2, 2-dimethyltetrahydrofuran [2,3-d ] [1,3] dioxolan-5-yl) ethane-1, 2-diol;

and 4, step 4: dissolving 3.1-7.2 g of product 4 in 100mL of Dichloromethane (DCM), and then dissolving 5.32-8.2 g (25mmoL) of sodium periodate (NaIO)₄) Adding the mixture into the solution in batches, stirring the mixture at room temperature for 1 hour, filtering reaction liquid, collecting filtrate, and concentrating the filtrate in vacuum until the filtrate is dried to obtain 2.78-4.5 g of a product 5: (3aR,5S,6S,6aR) -6- (benzyloxy) -2, 2-dimethyltetrahydrofuran [2,3-d][1,3]Dioxolane-5-aldehyde; and the yield of product 5 is 98%;

and 5: 2.78-4.5 g of the product 5, 5.6-9.2g (100mmol) of potassium hydroxide (KOH) and 20-40 mL of water are placed in a 100mL three-neck flask, fully stirred at the room temperature of 20-25 ℃, and added with 3.36-5.56 g (20mmol) of silver nitrate (AgNO)₃) Continuously stirring for 2 hours at room temperature; the reaction solution was filtered through a Buchner funnel with celite and the filtrate was collected, the pH of the filtrate was adjusted to 3 with 6N hydrochloric acid, extracted 3 times with 50-65 mL ethyl acetate (EtOAc), the organic phase was collected and washed with 10-20 g anhydrous sodium sulfate (Na)₂SO₄) Drying and vacuum concentrating to dryness to obtain 2.1-4.2 g of a white solid product 6: (3aR,5S,6S,6aR) -6- (benzyloxy) -2, 2-dimethyltetrahydrofuran [2,3-d][1,3]Dioxolane-5-carboxylic acid; the product 6 can be esterified with various alcohols, which is a common parent carboxylic acid, and the yield of the product 6 is 71 percent;

step 6: weighing 0.294-0.4 g of the product 6, 0.156-0.192 g (1mmol) of menthol, 0.0246-0.032 g (0.2mmol) of DMAP, 0.228-0.288 g (1.2mmol) of EDC, 0.202-0.282 g (2mmol) of Triethylamine (TEA) and 4-6 mL of Dichloromethane (DCM) into an 8-10 mL reaction bottle, and stirring at room temperature for 4 hours; washing the reaction solution with 10-20 mL of water, extracting with 5-10 mL of dichloromethane, drying the organic phase with anhydrous sodium sulfate, concentrating to dryness in vacuum, performing silica gel column chromatography, eluting with ethyl acetate and petroleum ether until ethyl acetate EtOAc (petroleum ether PE) ═ 1:1, and obtaining 0.19-0.36 g of a colorless viscous oil product 7: (1R,2S,5R) -2-isopropyl-5-methylcyclohexyl- (3aR,5S,6R,6aR) -6- (benzyloxy) -2, 2-dimethyltetrahydrofuran [2,3-d ] [1,3] dioxolane-5-carboxylate; and yield of product 7 was 44%;

and 7: placing 0.19-0.36 g of the product 7 and 5-15mL of methanol (MeOH) and 0.02-0.038 g of 10% palladium-carbon (Pd/C) in a 25mL hydrogenation bottle, replacing the system with hydrogen for 3 times, stirring at room temperature under 20atm of hydrogen pressure for 6 hours, filtering the reaction solution, collecting the filtrate, performing vacuum concentration on the filtrate by using a flash silica gel column chromatography, and eluting with dichloromethane and methanol according to DCM (MeOH) ═ 20:1 to finally obtain 0.095-0.18 g of a white solid product 8: (1R,2S,5R) -2-isopropyl-5-methylcyclohexyl- (3aR,5S,6R,6aR) -6- (hydroxy) -2, 2-dimethyltetrahydrofuran [2,3-d ] [1,3] dioxolane-5-carboxylate; and the yield of product 8 was 63%.

2. The method for synthesizing a release type xylonate spice for flavoring tobacco according to claim 1, wherein the method comprises the following steps: in the step 2, the reaction solution after the reaction further comprises the following processing steps: the first step is as follows: after the reaction, the reaction solution was carefully poured into 100mL of ice water, and extracted 3 times with 100mL of ethyl acetate (EtOAc); the second step is that: the extracted organic phases were combined and washed with 8-15 g of anhydrous sodium sulfate (Na)₂SO₄) Drying; the third step: concentrating the dried organic phase to dryness in vacuum, and performing silica gel column chromatography; elution with ethyl acetate (EtOAc) and Petroleum Ether (PE) at 1:4 gave product 3 as a colorless clear oil: (3aR,5R,6S,6aR) -6- (benzyloxy) -5- ((S) -2, 2-dimethyl-1, 3-dioxolan-4-yl) -2, 2-dimethyltetrahydrofuran [2,3-d ]][1,3]A dioxolane; and the yield of product 3 was 98.8%.

3. The synthesis method of a release-type xylonate perfume for perfuming tobacco according to claim 1 or 3, characterized in that: in the step 2, when the reaction solution after the completion of the reaction is checked for ethyl acetate (EtOAc)/Petroleum Ether (PE), i.e., EtOAc/PE, by thin layer chromatography, it is indicated that the reaction is completed when the ratio of EtOAc/PE is 1: 4.

4. The method for synthesizing a release type xylonate spice for flavoring tobacco according to claim 1, wherein the method comprises the following steps: in the step 3, the product after stirring for 24 hours at room temperature further comprises the following processing steps: the first step is as follows: vacuum concentration of acetic acid; the second step is that: 200mL of ethyl acetate were added, and 100mL of saturated sodium bicarbonate (NaHCO) were used₃) Washing the aqueous solution, extracting, separating and collecting an organic phase; the third step: the organic phase was washed once with 100ml of saturated aqueous sodium chloride solution and with anhydrous sodium sulfate (Na)₂SO₄) Drying and vacuum concentration to dryness gave product 4 in a colorless viscous oily state: (S) -1- ((3aR,5R,6S,6aR) -6- (benzyloxy) -2, 2-dimethyltetrahydrofuran [2,3-d][1,3]Dioxolan-5-yl) ethane-1, 2-diol; and the yield of product 4 was 100%.

5. The method of claim 1The synthesis method of the release type xylose ester spice for flavoring the tobacco is characterized by comprising the following steps of: the chemical molecular structural formula of the product 6 is

6. The method for synthesizing a release type xylonate spice for flavoring tobacco according to claim 1, wherein the method comprises the following steps: the chemical molecular structural formula of the product 8 is shown in the specification

Technical Field

The invention belongs to the technical field of chemical saccharide derivative preparation, and particularly relates to a synthesis method of a release type xylose ester perfume for perfuming tobacco.

Background

At present, in the tobacco flavoring technology: in the design of the novel release type tobacco flavor which replaces low-grade fatty acid, high-grade fatty acid, alcohols, phenols and the like and is easy to volatilize and lose in the tobacco flavoring and storing process, the release type tobacco flavor developed by taking the xylose as the target flavor is characterized in that: the release type tobacco flavor has a very small taste at normal temperature and normal pressure, and has smaller volatility in the adding period compared with the conventional sugar ester tobacco flavor, and the retention rate of the flavor after the tobacco leaves are flavored is higher; after the cigarette is burnt and smoked, the flavor can be more uniformly released after the cigarette is thermally cracked; meanwhile, the cigarette filter tip can effectively reduce the irritant miscellaneous gas during cigarette smoking, improve the quality of aroma, further improve the comprehensive advantages of various aspects such as aroma, taste and the like, and is gradually paid attention. In the prior art, xylitol and carboxylic acid are mostly adopted for synthesizing the xylose ester spice as ester, and the defects are that: in the synthetic route, the more extensive compounds of the xylose ester perfume cannot be obtained due to the limitation of the types of carboxylic acids. Besides, in addition to the synthetic products disclosed in the journal of tobacco science and technology, which is published in 2010 at 6/20 th, with the title of 1, 2-O-isopropylidene-3, 5-O-di (phenylethoxycarbonyl succinyl) xylofuranose and the application thereof in cigarettes, the development of a synthetic method of xylose ester with other characteristic aroma different from the synthetic route and process is urgently needed, and the following technical scheme is proposed.

Disclosure of Invention

The technical problems solved by the invention are as follows: the synthesis method of the release type xylose ester spice for flavoring the tobacco adopts the principle that carboxylic acid and alcohol are esterified to prepare the xylose ester through the obtained common parent carboxylic acid which can be esterified with various alcohol compounds, endows the cigarette smoke with the aroma characteristics of isovaleric acid, ethyl myrcene, 4-methylphenol and the like, and is used for flavoring production of the release type spice for the tobacco, so that the aroma quality and the aroma quantity of the cigarette smoke are improved, and the production requirement of the preparation of the release type spice for the cigarette is met.

The technical scheme adopted by the invention is as follows: the synthesis method of the release type xylose ester spice for flavoring the tobacco is characterized by comprising the following steps of: the method comprises the following steps:

step 1: 15-20 g (D +) g of glucose, 150-180-200 mL of anhydrous acetone, 1.25-1.82 g of anhydrous copper sulfate (CuSO)₄) 0.75-2.25 g of concentrated sulfuric acid (H)₂SO₄) Placing the mixture into a 500mL single-neck flask, stirring the mixture for 48 hours at an internal temperature, concentrating the mixture in vacuum, and using 80-120 mL of saturated sodium bicarbonate (NaHCO) to obtain crude oil₃) Washing, extraction 2 times with 50-95 mL ethyl acetate (EtOAc), combining the organic phases and adding anhydrous sodium sulfate (Na)₂SO₄) Drying and finally vacuum concentrating to obtain 18.95-28 g of white solid product 2: (3aR,5S,6S,6aR) -5- ((S) -2, 2-dimethyl-1, 3-dioxolan-4-yl) -2, 2-dimethyltetrahydrofuran [2,3-d ]][1,3]Dioxolan-6-ol; and the yield of product 2 is 95.3%; of product 2Structural characterization: HR-MS M/z 260.2, [ M + H]⁺。

Step 2: putting 3.5-7.2 g of the product 2 and 40-70 mL of anhydrous N, N-Dimethylformamide (DMF) into a 200-300 mL four-neck flask, uniformly stirring, and introducing nitrogen for protection; cooling to 0 ℃ in an ice bath, adding 0.85-1 g (24mmol) of 60% sodium hydride (NaH) into the solution in batches, and continuing stirring for 15-20 minutes at the temperature of 0 ℃ while generating bubbles; then slowly dropwise adding 2.8-4.05 g (20mmol) of benzyl bromide (BnBr) into the reaction bottle, and continuously stirring for 2 hours at the room temperature of 20-25 ℃ until the reaction is finished: the reaction solution after the completion of the reaction was extracted with ethyl acetate several times, and then anhydrous sodium sulfate (Na) was added₂SO₄) Drying and elution with 1:4 ethyl acetate (EtOAc) and Petroleum Ether (PE) afforded 5.25-8.2 g of product 3: (3aR,5R,6S,6aR) -6- (benzyloxy) -5- ((S) -2, 2-dimethyl-1, 3-dioxolan-4-yl) -2, 2-dimethyltetrahydrofuran [2,3-d ]][1,3]A dioxolane; structural characterization of product 3: HR-MS M/z 351.1, [ M + H]⁺。

And step 3: placing 5.25-8.2 g of the product 3 and 95% of 50-90 mL of acetic acid (AcOH) aqueous solution in a 250mL single-neck flask, and stirring at room temperature for 24 hours; after vacuum concentration, washing extraction and drying, 3.1-7.2 g of a product 4 is obtained: (S) -1- ((3aR,5R,6S,6aR) -6- (benzyloxy) -2, 2-dimethyltetrahydrofuran [2,3-d][1,3]Dioxolan-5-yl) ethane-1, 2-diol; structural characterization of product 4: HR-MS M/z 311.1, [ M + H]⁺。

And 4, step 4: dissolving 3.1-7.2 g of product 4 in 100mL of Dichloromethane (DCM), and then dissolving 5.32-8.2 g (25mmoL) of sodium periodate (NaIO)₄) Adding the mixture into the solution in batches, stirring the mixture at room temperature for 1 hour, filtering reaction liquid, collecting filtrate, and concentrating the filtrate in vacuum until the filtrate is dried to obtain 2.78-4.5 g of a product 5: (3aR,5S,6S,6aR) -6- (benzyloxy) -2, 2-dimethyltetrahydrofuran [2,3-d][1,3]Dioxolane-5-aldehyde; and the yield of product 5 is 98%; structural characterization of product 5: HR-MS M/z 279.1, [ M + H]⁺。

And 5: 2.78-4.5 g of the product 5, 5.6-9.2g (100mmol) of potassium hydroxide (KOH) and 20-40 mL of water are placed in a 100mL three-neck flask, fully stirred at the room temperature of 20-25 ℃, and added with 3.36-5.56 g (20mmol) of silver nitrate (AgNO)₃) Continuously stirring for 2 hours at room temperature; the reaction solution was filtered through a Buchner funnel with celite and the filtrate was collected, the pH of the filtrate was adjusted to 3 with 6N hydrochloric acid, extracted 3 times with 50-65 mL ethyl acetate (EtOAc), the organic phase was collected and washed with 10-20 g anhydrous sodium sulfate (Na)₂SO₄) Drying and vacuum concentrating to dryness to obtain 2.1-4.2 g of a white solid product 6: (3aR,5S,6S,6aR) -6- (benzyloxy) -2, 2-dimethyltetrahydrofuran [2,3-d][1,3]Dioxolane-5-carboxylic acid; product 6 can be esterified with a variety of alcohols, it is a common parent carboxylic acid, and the yield of product 6 is 71%; structural characterization of product 6: HR-MS M/z 295.1, [ M + H]⁺。

Step 6: weighing 0.294-0.4 g of the product 6, 0.156-0.192 g (1mmol) of menthol, 0.0246-0.032 g (0.2mmol) of DMAP, 0.228-0.288 g (1.2mmol) of EDC, 0.202-0.282 g (2mmol) of Triethylamine (TEA) and 4-6 mL of Dichloromethane (DCM) into an 8-10 mL reaction bottle, and stirring at room temperature for 4 hours; washing the reaction solution with 10-20 mL of water, extracting with 5-10 mL of dichloromethane, and extracting with anhydrous sodium sulfate (Na)₂SO₄) The organic phase was dried, concentrated to dryness in vacuo and chromatographed on silica gel, eluting with ethyl acetate and petroleum ether to ethyl acetate EtOAc, petroleum ether PE ═ 1:1, to give 0.19 to 0.36g of product 7 in the colourless viscous oily state: (1R,2S,5R) -2-isopropyl-5-methylcyclohexyl- (3aR,5S,6R,6aR) -6- (benzyloxy) -2, 2-dimethyltetrahydrofuran [2,3-d ]][1,3]Dioxolane-5-carboxylic acid ester; and yield of product 7 was 44%; structural characterization of product 7: HR-MS M/z 433.2, [ M + H]⁺。

And 7: placing 0.19-0.36 g of the product 7 and 5-15mL of methanol (MeOH) and 10% of 0.02-0.038 g of palladium carbon in a 25mL hydrogenation bottle, replacing the system with hydrogen for 3 times, stirring at room temperature under the hydrogen pressure of 20atm for 6 hours, filtering the reaction solution, collecting the filtrate, performing vacuum concentration on the filtrate, performing flash silica gel column chromatography, and eluting with dichloromethane and methanol according to DCM (MeOH: 20: 1) to finally obtain 0.095-0.18 g of a white solid product 8: (1R,2S,5R) -2-isopropyl-5-methylcyclohexyl- (3aR,5S,6R,6aR) -6- (hydroxy) -2, 2-dimethyltetrahydrofuran [2,3-d ]][1,3]Dioxolane-5-carboxylic acid ester; and the yield of product 8 was 63%; structural characterization of product 8: HR-MS M/z 432.5, [ M + H]⁺。1H NMR(300MHz,DMSO-d6)δ5.94(d,J＝3.5Hz,1H),5.66(d,J＝5.7Hz,1H),4.74–4.60(m,2H),4.43(d,J＝3.6Hz,1H),4.21(dd,J＝5.8,3.4Hz,1H),1.98–1.80(m,2H),1.71–1.57(m,2H),1.32(d,J＝45.5Hz,9H),1.15–0.94(m,2H),0.87(t,J＝6.5Hz,7H),0.72(d,J＝6.9Hz,3H)。

In the above technical scheme, in order to improve the yield of the product 3 in the step 2, further: in the step 2, the reaction solution after the reaction further comprises the following processing steps: the first step is as follows: after the reaction, the reaction solution was carefully poured into 100mL of ice water, and extracted 3 times with 100mL of ethyl acetate (EtOAc); the second step is that: the extracted organic phases were combined and washed with 8-15 g of anhydrous sodium sulfate (Na)₂SO₄) Drying; the third step: concentrating the dried organic phase to dryness in vacuum, and performing silica gel column chromatography; elution with ethyl acetate (EtOAc) and Petroleum Ether (PE) at 1:4 gave product 3 as a colorless clear oil: (3aR,5R,6S,6aR) -6- (benzyloxy) -5- ((S) -2, 2-dimethyl-1, 3-dioxolan-4-yl) -2, 2-dimethyltetrahydrofuran [2,3-d ]][1,3]A dioxolane; and the yield of product 3 was 98.8%.

In the above technical solution, to quantitatively determine whether the reaction of step 2 is completed, further: in the step 2, when the reaction solution after the completion of the reaction is checked for ethyl acetate (EtOAc)/Petroleum Ether (PE), i.e., EtOAc/PE, by thin layer chromatography, it is indicated that the reaction is completed when the ratio of EtOAc/PE is 1: 4.

In the above technical scheme, in order to maximize the yield of the product 4 in the step 3, further: in the step 3, the product after stirring for 24 hours at room temperature further comprises the following processing steps: the first step is as follows: vacuum concentration of acetic acid; the second step is that: 200mL of ethyl acetate were added, and 100mL of saturated sodium bicarbonate (NaHCO) were used₃) Washing the aqueous solution, extracting, separating and collecting an organic phase; the third step: the organic phase was washed once with 100ml of saturated aqueous sodium chloride solution and with anhydrous sodium sulfate (Na)₂SO₄) Drying and vacuum concentration to dryness gave product 4 in a colorless viscous oily state: (S) -1- ((3aR,5R,6S,6aR) -6- (benzyloxy) -2, 2-dimethyltetrahydrofuran [2,3-d][1,3]Dioxolan-5-yl) ethane-1, 2-diol; and the yield of product 4 was 100%.

Wherein the chemical molecular structural formula of the product 6 is shown in the specification

Wherein the chemical molecular structural formula of the product 8 is shown as

The synthesis principle is as follows: the technical scheme adopts a new synthesis method to synthesize the xylose ester, and overcomes the technical problem that the prior art adopts xylitol and carboxylic acid as ester and the synthesis of the xylose ester is limited by the type of the carboxylic acid; alternatively, xylitol derivative xylose carboxylic acid and alcohol are used as ester; thereby being beneficial to synthesizing more extensive and better xylonate spice compounds; namely, the parent carboxylic acid of the product 6 obtained in the reaction route is used, and various alcohol compounds can be selected to perform esterification reaction with the product 6 by using the parent carboxylic acid of the product 6, so that a wider range of higher-quality xylose ester spice compounds can be obtained, and the xylose ester spice compounds can be used for perfuming cigarette release type perfuming spices.

Compared with the prior art, the invention can realize the following effects:

1. the product 8-xylose ester obtained by the scheme is a release type tobacco flavor, and the release type tobacco flavor has very small taste at normal temperature and normal pressure after being added and applied to flavoring of tobacco leaves; the volatility of the perfume in the adding period is lower, and the perfuming retention rate is higher; but after the cigarette is burnt and thermally cracked, the fragrance can be more uniformly released; can be used as a flavoring additive for a high-quality release type xylose ester cigarette flavor;

2. after the xylose ester product 8 obtained by the scheme is added into tobacco leaves with the same adding content, GC/MS analysis is carried out on the relative content heat components of the smoke components at the cracking temperature of 300 ℃, 600 ℃ and 900 ℃ after the product 8 with the same adding content is added into the tobacco leaves, and not less than fifty odorous aldehyde, ketone, acid and ester compounds can be obtained in total; when the addition amount of the compound in tobacco is 0.01%, the cigarette aroma quality can be obviously improved; the obtained smoke is soft and exquisite, the quality of aroma is improved, the aroma amount is obviously increased, the harmony is better, the aftertaste is purer and richer, the irritation is lower, and the tobacco aroma is more harmonious and lingering in smoking result evaluation;

3. the product 8 xylan ester synthesized by the scheme is used for perfuming cigarettes, and compared with the published documents: liuyun is the first author, research and development personnel of our prescription participate in Liuyun, and in the published title of 1, 2-O-isopropylidene-3, 5-O-di (phenylethoxycarbonyl succinyl) xylofuranose which is published in the journal of tobacco science and technology in 2010 at 6-20 days, and the final product (1, 2-O-isopropylidene-3, 5-O-di (phenylethoxycarbonyl succinyl) xylofuranose) mentioned in the published journal literature of tobacco science and application thereof in cigarettes, the final product xylose ester can endow the cigarette smoke with the aroma characteristics of isovaleric acid, ethyl myrcene, 4-methylphenol and the like, so that the cigarette smoke is softer and finer, the harmonious property is increased, and the aftertaste becomes pure.

Drawings

FIG. 1 is a process flow diagram of the present invention;

FIG. 2 is the nuclear magnetic resonance hydrogen spectrum of xylose ester containing a certain alcohol compound group of the product 8 xylose ester of the invention.

Detailed Description

Specific embodiments of the present invention are described below with reference to fig. 1-2. It is to be understood that the following description of the embodiments is merely exemplary and not intended to limit the invention in any way.

The following examples are given to facilitate a better understanding of the invention, but do not limit the invention. The experimental procedures in the following examples are conventional unless otherwise specified. The test materials used in the following examples were either commercially available, analytically pure or chemically pure, unless otherwise specified.