Preparation method and application of 5-methyl furfuryl alcohol-beta-D-glucoside

A technology of methyl furfuryl alcohol and glucoside, which is applied in the field of tobacco flavors, can solve the problems of easy volatilization of 5-methyl furfuryl alcohol and easy loss of flavor, and achieve the effects of simple post-processing, reducing miscellaneous gas, and improving volatilization

Inactive Publication Date: 2018-08-24
ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The present invention proposes the preparation method and application of 5-methylfurfuryl alcohol-β-D-glucoside, which solves the technical problems that 5-methylfurfuryl alcohol is easy to volatilize and the fragrance is easy to lose in the prior art

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  • Preparation method and application of 5-methyl furfuryl alcohol-beta-D-glucoside
  • Preparation method and application of 5-methyl furfuryl alcohol-beta-D-glucoside
  • Preparation method and application of 5-methyl furfuryl alcohol-beta-D-glucoside

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Embodiment 1

[0037] The preparation method of 5-methylfurfuryl alcohol-β-D-glucoside of this embodiment is:

[0038] (1) Synthesis of 5-methylfurfuryl alcohol-β-D-tetraacetyl glucoside (Ⅱ):

[0039] Dissolve 0.56 g (5 mmol) of 5-methylfurfuryl alcohol and 2.98 g (6 mmol) of trichloroacetimide ester sugar in 15 mL of dry dichloromethane, add 1 g of freshly baked 4 Å molecular sieve, and stir at room temperature After 10 min, cool to -20 ℃, add 1.41g (10 mmol) BF 3 •Et 2 O continued to incubate the reaction for 2 h, and TLC detected the progress of the reaction. After the reaction, 30 mL of dichloromethane was added, shaken, and separated. The organic phase was washed 3 times with saturated sodium carbonate solution and 3 times with saturated brine. The organic phase was separated, dried with anhydrous sodium sulfate overnight, filtered, and depressurized. After concentration, it is separated and purified by silica gel column chromatography [ V (Petroleum ether): V (Ethyl acetate)=4:1] to obtain...

Embodiment 2

[0049] The preparation method of 5-methylfurfuryl alcohol-β-D-glucoside of this embodiment is:

[0050] (1) Synthesis of 5-methylfurfuryl alcohol-β-D-tetraacetyl glucoside (Ⅱ):

[0051] Dissolve 0.56 g (5 mmol) of 5-methylfurfuryl alcohol and 4.96 g (10 mmol) of trichloroacetimide ester sugar in 20 mL of dry dichloromethane, add 2 g of freshly baked anhydrous calcium sulfate, at room temperature Stir for 10 min and then cool to -20 ℃, add 2.12 g (15 mmol) BF 3 •Et 2 O continued to incubate the reaction for 1 h, and TLC checked the progress of the reaction. After the reaction, add 30 mL of dichloromethane, shake, and separate. The organic phase was washed 4 times with saturated sodium carbonate solution and 4 times with saturated brine. The organic phase was separated, dried with anhydrous sodium sulfate overnight, filtered, and depressurized. After concentration, it is separated and purified by silica gel column chromatography [ V (Petroleum ether): V (Ethyl acetate)=4:1], 1.70 g ...

Embodiment 3

[0057] The preparation method of 5-methylfurfuryl alcohol-β-D-glucoside of this embodiment is:

[0058] (1) Synthesis of 5-methylfurfuryl alcohol-β-D-tetraacetyl glucoside (Ⅱ):

[0059] Dissolve 0.56 g (5 mmol) of 5-methylfurfuryl alcohol and 3.72 g (10 mmol) of trichloroacetimide ester sugar in 20 mL of dry dichloromethane, add 2 g of freshly baked anhydrous calcium sulfate, at room temperature Stir for 10 min and then cool to -20 ℃, add 1.41 g (15 mmol) BF 3 •Et 2 O continued to incubate the reaction for 2 h, and TLC detected the progress of the reaction. After the reaction, add 30 mL of dichloromethane, shake, and separate. The organic phase was washed 5 times with saturated sodium carbonate solution and 5 times with saturated brine. The organic phase was separated, dried with anhydrous sodium sulfate overnight, filtered, and depressurized. After concentration, it is separated and purified by silica gel column chromatography [ V (Petroleum ether): V (Ethyl acetate)=3:1], 1.75g ...

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Abstract

The invention provides a preparation method of 5-methyl furfuryl alcohol-beta-D-glucoside. The preparation method is characterized in that firstly, trichloroacetimidate sugar and 5-methyl furfuryl aresubjected to glycosylation reaction; then, a methanol solution of sodium methoxide is used for deacetylation to obtain the 5-methyl furfuryl alcohol-beta-D-glucoside. The method has the advantages that the reaction conditions are mild; the aftertreatment is simple; through simple and short steps, the preparation of the 5-methyl furfuryl alcohol-beta-D-glucoside is convenient. When the 5-methyl furfuryl alcohol-beta-D-glucoside is applied into cigarettes for perfuming, the fragrance quality and the fragrance quantity of the cigarettes can be improved; the farraginous gas is lightened; the irritation is reduced; the aftertaste is pure. The 5-methyl furfuryl alcohol-beta-D-glucoside has good cigarette perfuming stability.

Description

Technical field [0001] The invention belongs to the technical field of flavors for tobacco, relates to the application of flavors in cigarettes, in particular to the preparation method and application of 5-methylfurfuryl alcohol-β-D-glucoside. Background technique [0002] With the improvement of people’s health awareness, the safety of cigarettes has attracted increasing attention. Reducing the amount of tar is an important means to improve the safety of cigarettes. However, as the amount of tar decreases, the smell of cigarettes becomes weaker and the aroma is weakened, making it difficult for consumers Accepted. Therefore, how to reduce the tar content while maintaining the flavor and aroma of cigarettes is a difficult problem faced by the tobacco industry. In order to enhance and increase the smoke concentration and flavor of cigarettes, flavoring is an effective method. [0003] One part of traditional tobacco flavors is the substance contained in tobacco itself, and the other...

Claims

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Application Information

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IPC IPC(8): C07H15/26C07H1/00A24B3/12
CPCA24B3/12C07H1/00C07H15/26
Inventor 张改红白冰杨静程传玲贾春晓毛多斌
Owner ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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