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Synthesis method for glucose tetra-ester in tobacco

A synthesis method and glucose technology are applied in the field of tobacco flavors and achieve the effects of remarkable industrial application value, easy operation and obvious effect.

Active Publication Date: 2009-04-08
CHINA TOBACCO HENAN IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, there is no report on the synthesis of this substance at home and abroad.

Method used

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  • Synthesis method for glucose tetra-ester in tobacco
  • Synthesis method for glucose tetra-ester in tobacco
  • Synthesis method for glucose tetra-ester in tobacco

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] (1) 6-O-trityl-β-D-methylglucopyranoside (compound of formula (II))

[0033] Add 10.0g β-D-methylglucopyranoside (compound of formula (I)), 16.0g triphenylchloromethane and 100mL pyridine into a 250mL three-necked flask, stir at 100°C for 1h, and pour the reaction solution into In 200mL ice water, extract 3 times with 50mL dichloromethane each time, combine the extracts and wash 2 times with saturated ammonium chloride solution, each time 50mL, then wash several times with ice water, dry over anhydrous sodium sulfate, filter, The syrupy object after removal of the solvent was recrystallized with absolute ethanol to obtain 14.6 g of product with a yield of 65% and a melting point of 155-156° C. (the thermometer was calibrated); it was confirmed to be the target product by infrared and nuclear magnetic resonance analysis. (2) 2,3,4-triisobutyric acid-6-O-trityl-β-D-methylglucopyranoside (compound of formula (III))

[0034] In a 100mL three-necked flask equipped with a ma...

Embodiment 2

[0042] In step (1), control the ratio of β-D-methylglucopyranoside and triphenylchloromethane to 1:1.1, add 30 mL of pyridine, and stir at 100° C. for 1 h. Others are the same as step (1) of Example 1, and the yield of the compound of formula (II) is 65.10%.

[0043] Subsequent steps are the same as in Example 1.

Embodiment 3

[0045] In step (1), control the ratio of β-D-methylglucopyranoside to triphenylchloromethane as 1:1.2, add 25 mL of pyridine, and stir at 100° C. for 1.5 h. Others are the same as step (1) of Example 1, and the yield of the compound of formula (II) is 65.43%.

[0046] Subsequent steps are the same as in Example 1.

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Abstract

The invention belongs to the research field of spice for tobacco, and particularly relates to a synthetic method of glucose tetraesters. The glucose tetraesters is demonstrated in formula VI. According to the principle that things with reasonable price are easy to obtain, common market materials are selected as a raw material and a reagent for use. The synthetic method is easy to operate; and as the glucose tetraesters synthesized affect tobacco products significantly, the synthetic method has the advantages of significant value in industrial applications and broad prospects of popularization and application.

Description

(1) Technical field [0001] The invention belongs to the research field of tobacco spices, in particular to a method for synthesizing glucose tetraester. (2) Background technology [0002] In 1970, Schumacher et al. first isolated 6-O-acetyl-2,3,4-tri-O-(3-methylpentanoyl)-β-D-glucopyranose from Turkish oriental tobacco, and identified its chemical structure; research since then has shown the presence of a range of compounds with this structure in tobacco. 6-O-acetyl-2,3,4-tri-O-isobutyryl-β-D-glucopyranose belongs to one of the above-mentioned glucopyranose ester compounds, which is a kind of tobacco products naturally present in tobacco The fragrance precursor with positive contribution to quality has very stable physical properties, and can only be cracked under high temperature conditions to release free isobutyric acid. So far, there is no report on the synthesis of this substance at home and abroad. (3) Contents of the invention [0003] The object of the present i...

Claims

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Application Information

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IPC IPC(8): C07H13/04C07H1/06
Inventor 马宇平陈芝飞孙志涛刘强戴建国王保会
Owner CHINA TOBACCO HENAN IND
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