Synthesis method of release-type xylose ester fragrance for tobacco flavoring

A technology of tobacco flavoring and synthesis method, which is applied in the direction of essential oils/flavors, tobacco, and processed tobacco. It can solve the problems of inability to obtain xylose ester flavor compounds and restrictions, and achieve pure and rich aftertaste, increased aroma, and coordination. Good results

Active Publication Date: 2021-10-22
CHINA TOBACCO SHAANXI IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Under the prior art, the synthesis of xylose ester fragrances mostly uses xylitol and carboxylic acid synthesis as esters. The disadvantage is that in the synthesis route, limited by the type of carboxylic acid, it is impossible to obtain a wider range of xylose ester fragrance compounds

Method used

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  • Synthesis method of release-type xylose ester fragrance for tobacco flavoring
  • Synthesis method of release-type xylose ester fragrance for tobacco flavoring
  • Synthesis method of release-type xylose ester fragrance for tobacco flavoring

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The release type xylose ester perfume synthesis method for tobacco flavoring is characterized in that: comprising the following steps:

[0028] Step 1: 15g (D+) glucose, 150mL of anhydrous acetone, 1.25g of anhydrous copper sulfate (CuSO 4 ), 0.75g concentrated sulfuric acid (H 2 SO 4 ) was placed in a 500mL single-necked flask and stirred at room temperature with a stirrer for 48h, concentrated in vacuo, and the crude product oil obtained was washed with 80mL of saturated sodium bicarbonate (NaHCO 3 ) washing, 50mL ethyl acetate (EtOAc) extraction twice, combined organic phase, and with anhydrous sodium sulfate (Na 2 SO 4 ) and finally concentrated in vacuo to obtain 18.95 g of white solid product 2: (3aR,5S,6S,6aR)-5-((S)-2,2-dimethyl-1,3-dioxolane-4- base)-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolan-6-ol; and the yield of product 2 was 95.3%; the structural characterization of product 2: HR -MS m / z:260.2,[M+H] + .

[0029] Step 2: Take 3.5g of product 2 an...

Embodiment 2

[0042] The release type xylose ester perfume synthesis method for tobacco flavoring is characterized in that: comprising the following steps:

[0043] Step 1: 18g (D+) glucose, 180mL of anhydrous acetone, 1.58g of anhydrous copper sulfate (CuSO 4 ), 0.98g concentrated sulfuric acid (H 2 SO 4 ) was placed in a 500mL single-necked flask and stirred at room temperature with a stirrer for 48h, concentrated in vacuo, and the crude product oil obtained was washed with 100mL of saturated sodium bicarbonate (NaHCO 3 ) washing, 70mL ethyl acetate (EtOAc) extraction twice, combined organic phase, and with anhydrous sodium sulfate (Na 2 SO 4 ) and finally concentrated in vacuo to obtain 24.8 g of white solid product 2: (3aR,5S,6S,6aR)-5-((S)-2,2-dimethyl-1,3-dioxolane-4- base)-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolan-6-ol; and the yield of product 2 was 95.3%; and the yield of product 2 was 95.3%; Structural characterization: HR-MS m / z: 260.2, [M+H] + .

[0044] Step 2: Tak...

Embodiment 3

[0057] The release type xylose ester perfume synthesis method for tobacco flavoring is characterized in that: comprising the following steps:

[0058] Step 1: 20g (D+) glucose, 200mL of anhydrous acetone, 1.82g of anhydrous copper sulfate (CuSO 4 ), 2.25g concentrated sulfuric acid (H 2 SO 4 ) was placed in a 500mL single-necked flask and stirred at room temperature with a stirrer for 48h, concentrated in vacuo, and the obtained crude product oil was washed with 120mL of saturated sodium bicarbonate (NaHCO 3 ) washing, 95mL ethyl acetate (EtOAc) extraction twice, combined organic phase, and with anhydrous sodium sulfate (Na 2 SO 4 ) and finally concentrated in vacuo to give 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 was 95.3%; structural characterization: HR-MS m / z:260.2,[M+H] + .

[0059] Step 2: Take 7.2g of product 2 and 70mL of anhydrous N,N-...

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Abstract

Provides a method for synthesizing release-type xylose ester flavoring for tobacco flavoring, uses glucose as raw material, adopts the principle of esterification of carboxylic acid and alcohol to make ester, and obtains a compound that can be used in esterification reaction with various alcohol compounds Parent carboxylic acid (see product 6): (3aR,5S,6S,6aR)‑6‑(benzyloxy)‑2,2‑dimethyltetrahydrofuran[2,3‑d][1,3]dioxolane Cyclo-5-carboxylic acid; thus compounding with a variety of alcohols to synthesize higher-quality and broader xylose esters (see 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, for tobacco Flavoring production of release-type flavors, thereby improving the aroma and aroma of cigarette smoke, which can meet the needs of self-production and addition of domestic release-type flavors for cigarettes, and endow cigarette smoke with isovaleric acid, ethyl myrcene, and 4-methylphenol The aroma characteristics of cigarettes make the cigarette smoke softer and more delicate, the harmony is increased, and the aftertaste becomes pure.

Description

technical field [0001] The invention belongs to the technical field of preparation of chemical sugar derivatives, and in particular relates to a method for synthesizing release-type xylose ester flavoring used for flavoring tobacco. Background technique [0002] At present, in tobacco flavoring technology: in the design of new release-type tobacco flavors that replace low-level fatty acids, high-level fatty acids, alcohols, phenols, etc., which are easy to volatilize and lose during tobacco leaf flavoring and storage, the xylose ester as the target flavoring research and development Release-type tobacco flavors are characterized by: release-type tobacco flavors have a small taste at normal temperature and pressure, and are less volatile than conventional sugar ester tobacco flavors during the addition period, and the retention rate of flavors after flavoring tobacco leaves higher; and after the pyrolysis occurs when the cigarette is smoked, the aroma can be released more eve...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H1/00C07H9/04A24B3/12A24B15/26C11B9/00
CPCA24B3/12A24B15/26C11B9/0015
Inventor 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樊亚玲何育萍
Owner CHINA TOBACCO SHAANXI IND
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