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Simple method for synthesizing cedrol glucoside

A technology of glucoside and synthesis method, which is applied in the direction of chemical instruments and methods, sugar derivatives, sugar derivatives, etc. It can solve the problems of restricting the industrial production of products, complicated purification methods, and affecting manufacturing costs, etc., and achieves convenient operation and simple process , the effect of high yield

Pending Publication Date: 2019-02-22
HUABAO FLAVOURS & FRAGRANCES CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a woody fragrance, cedaryl alcohol has a pleasant and long-lasting cedarwood aroma. It has been widely used in the fields of daily chemicals and tobacco. However, it has a high melting point and good thermal stability. The conditions are harsh and the purification method is complicated. The reaction intermediate cedaryl alcohol tetraacetyl glucoside needs to be repeatedly extracted with various solvents and crystallized in the volatile solvent ether (Liebigs Annalen der Chemie, Vol 1985, Issue 8, Page 1513-1536 ), which greatly affects the manufacturing cost and limits the industrial production of products

Method used

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  • Simple method for synthesizing cedrol glucoside

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Embodiment 1

[0028] The present embodiment synthesizes cedaryl alcohol glucoside according to the following steps:

[0029] Step 1: Synthesis of Crude Cedaryl Alcohol Tetraacetylglucoside (Compound 1)

[0030] Add 22.2g cedaryl alcohol, 41.1g bromotetraacetylglucose, 3g 4A molecular sieves, 27.6g silver carbonate, 100mL dichloromethane into a 250mL three-neck round bottom flask, stir at room temperature for 2h, after the reaction is over, filter to remove the solid, and the filtrate is passed through Concentration obtained 53.5 g of cedaryl alcohol tetraacetyl glucoside crude product, yield 96.9%.

[0031] Step 2: Synthesis of cederyl alcohol glucoside (compound 2)

[0032] Dissolve 53.5 g of cedarwood alcohol tetraacetyl glucoside crude product obtained in step 1 in 400 mL of methanol, add 1 mL of methanol solution of sodium methoxide, stir at room temperature, after the reaction, adjust the pH of the solution to neutral with cation exchange resin, add activated carbon Stir at 50°C for ...

Embodiment 2

[0034] The present embodiment synthesizes cedaryl alcohol glucoside according to the following steps:

[0035] Step 1: Synthesis of Crude Cedaryl Alcohol Tetraacetylglucoside (Compound 1)

[0036] Add 44.4g cedarwood alcohol, 84g bromotetraacetylglucose, 8g 4A molecular sieve, 55.2g silver carbonate, 250mL dichloromethane into a 500mL three-neck round bottom flask, stir at room temperature for 2h, after the reaction is over, filter to remove the solid, and the filtrate is concentrated Obtain 110 g of cedaryl alcohol tetraacetyl glucoside crude product, yield 98%.

[0037] Step 2: Synthesis of cederyl alcohol glucoside (compound 2)

[0038] Dissolve 110g of cedarwood alcohol tetraacetylglucoside crude product obtained in step 1 in 800mL of methanol, add 3mL of methanol solution of sodium methoxide, and stir at room temperature. Stir at 50°C for 45 minutes to decolorize, after filtration, concentrate the filtrate to remove the solvent, wash the remaining solid with 3×50mL ethy...

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Abstract

The invention discloses a simple method for synthesizing cedrol glucoside. The simple method is characterized in that a structural formula is shown in the specification. Cedrol serving as a raw material reacts with bromotetraacetyl glucose to obtain crude cedrol tetraacetyl glucoside; the next-step de-protection reaction can be directly performed without purification, and a final product is subjected to simple activated carbon decoloration and solvent washing to obtain cedrol glucoside. The simple method is simple in process, mild in condition, convenient to operate, high in yield and suitablefor industrial production.

Description

technical field [0001] The invention relates to a method for conveniently synthesizing cedryl alcohol glucoside. Background technique [0002] Glycosides are precursors of many natural fragrances, which exist in natural plants and can release fragrance components combined with sugar groups through biological enzymes, high temperature or hydrolysis. Glycosides, as a class of important latent fragrances, have no or very weak odor, no or very low volatility, can exist stably for a long time at room temperature, and generally do not volatilize and lose under processing or storage conditions. Only under certain conditions can the aroma substances be released, and can be widely used in the fields of food and daily chemical flavors and fragrances. For example, due to its high melting point and good stability, ethyl vanillin glucoside has been widely used to replace ethyl vanillin in cigarettes and baked goods, which can effectively improve the slow-release properties of spices, H...

Claims

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Application Information

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IPC IPC(8): C07H15/24C07H1/00C07H1/06
CPCC07H1/00C07H1/06C07H15/24
Inventor 邬帅帆黄艳崔秀明杨君夏炎康明娥徐晓炯
Owner HUABAO FLAVOURS & FRAGRANCES CO LTD
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