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Preparation method and application of effective ingredients of rose fragrance emitting agent for cigarettes

An effective ingredient, the technology of rose fragrance, which is applied in the synthesis and application of tobacco flavors and fragrances, and achieves the effects of simple reaction steps, easy crystallization and purification, and high yield

Inactive Publication Date: 2009-09-02
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The application of flavor release agents in cigarette flavoring is still in the preliminary development stage, and due to the secrecy of relevant enterprises in various countries, there are few reports on the application of flavor release agents for cigarettes

Method used

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  • Preparation method and application of effective ingredients of rose fragrance emitting agent for cigarettes
  • Preparation method and application of effective ingredients of rose fragrance emitting agent for cigarettes
  • Preparation method and application of effective ingredients of rose fragrance emitting agent for cigarettes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1: Synthesis of 2,3,4,6-tetra-O-acetyl-α-D-bromoglucopyranose

[0024] The specific operation process in this example is as follows: put a 250mL flask with a stirrer in an ice-water bath, add 0.424mol (40mL) acetic anhydride, cool to 4°C, add 0.24mL 60% perchloric acid dropwise under stirring . The ice-water bath was removed, the reaction mixture was returned to room temperature, and 0.056 mol of dry powdered glucose was added in batches under stirring to maintain the temperature of the reaction mixture at 30-40°C. Cool to 20 °C, add 0.1 mol (3.1 g) red phosphorus, and then add 0.226 mol (5.8 ml) bromine dropwise so that the temperature does not exceed 20 °C. After cooling, 3.6 mL of water was added with stirring to keep the reaction temperature not exceeding 20 ° C; the reaction mixture was left at room temperature for 2 h, diluted with 30 mL of dichloromethane, and filtered. Wash twice with 80 mL of ice water, then wash with 50 mL of saturated sodium bicarbo...

Embodiment 2

[0027] Example 2: Synthesis of phenylethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

[0028]The specific operation process is as follows: In a 250 mL round bottom flask, add 0.06 mol (7.32 g) of phenylethyl alcohol, 0.03 mol (8.28 g) of silver carbonate, 10 g of anhydrous calcium sulfate, and 50 mL of dichloromethane. The above mixture was stirred for half an hour. Dissolve 0.03mol (12.3g) of α-acetylglucosinobromide in 50mL of dichloromethane, add it to the above mixture, continue stirring for 24 hours, filter the mixture through a thin layer of diatomaceous earth, and distill off the solvent under reduced pressure; Purification by silica gel chromatography (petroleum ether: ethyl acetate = 5:1) to obtain the pure product of phenylethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside , melting point 102-104°C, yield 86%.

[0029] The reaction process can be expressed as:

[0030]

[0031] The reaction steps of the present invention are simple, and the target compound can b...

Embodiment 3

[0032] Embodiment 3: the preparation of rose-flavored flavor release agent for cigarettes

[0033] (1) Using phenylethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside as the main component

[0034] (2) Materials and dosage (mass unit: g): Glucose 0.5, absolute ethanol 100, phenylethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 2.5, Water 2.7, propylene glycol 2.0;

[0035] (3) Feed in the reaction kettle according to the formula, stir and heat up to 80-90°C, and reflux for 2.5 hours;

[0036] (4) After the reaction is completed, transfer the reaction liquid in the reactor to the cooling tank and cool to room temperature. After cooling to room temperature, add 0.6-1.2% potassium sorbate, stir evenly, and then pack into barrels to obtain the product.

[0037] Structural Analysis of Phenylethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

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Abstract

The invention discloses a preparation method and an application of effective ingredients of a rose fragrance emitting agent for cigarettes. The method comprises the following steps: utilizing a Cohen-Kohler reaction to prepare phenylethyl2,3,4,6-4-O-acetyl-beta-D-glucopyranoside; acetylizing glucose under the catalysis of perchloric acid and reacting with hydrogen bromide; removing solvent and recrystallizing in aether to obtain a white crystal of alpha-acetyl-1-bromoglucose; carrying out a photophobic reaction of the white crystal of alpha-acetyl-1-bromoglucose, phenylethyl alcohol and silver carbonate in a ratio of 1:2:1, removing the solvent and purifying by gel chromatography columns to obtain a purified phenylethyl2,3,4,6-4-O-acetyl-beta-D-glucopyranoside product. The prepared phenylethyl2,3,4,6-4-O-acetyl-beta-D-glucopyranoside cracks about 350 DEG C and can emit rose fragrance in main smoke and branch smoke. The prepared rose fragrance emitting agent uses the phenylethyl2,3,4,6-4-O-acetyl-beta-D-glucopyranoside as a main ingredient, can effectively emit objective fragrance ingredients and has the advantages of simple and easily-obtained raw materials, low cost and simple reaction equipment.

Description

technical field [0001] The invention belongs to the technical field of synthesis and application of flavors and fragrances for tobacco, and in particular relates to the synthesis of phenylethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside and rose-flavored cigarettes. Preparation of flavor release agent and its application in cigarette flavoring and addition. Background technique [0002] In the cigarette production process, many conventional tobacco flavors and fragrances have problems such as strong volatility and easy sublimation. On the other hand, too much flavor and fragrance for tobacco may destroy the natural fragrance of tobacco. However, simply developing some volatile flavors and fragrances with special aroma, which can coordinate with cigarette aroma and make smoke slightly better or fuller aroma, and apply them in cigarette manufacturing to improve the quality of cigarette products has little effect. [0003] In order to improve the shortcomings of strong volati...

Claims

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Application Information

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IPC IPC(8): C07H15/18C07H1/00A24B15/40
Inventor 苏庆德李珲蔡继宝谢卫刘泽春黄华
Owner UNIV OF SCI & TECH OF CHINA
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