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Aromatic acid DDMP diester sweetening agents as well as preparation method and application thereof

A technology for aromatic acids and sweeteners, which is applied in the field of tobacco flavor synthesis, and can solve the problems of poor stability, inability to use tobacco sweeteners, and easy deterioration and damage.

Active Publication Date: 2020-03-13
CHINA TOBACCO HENAN IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a sweetener of aromatic acid DDMP diester, preparation method and application, to solve the problem of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyridine in the prior art Pyran-4-one has poor stability and is easy to deteriorate and damage, so it cannot be used as a tobacco sweetener

Method used

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  • Aromatic acid DDMP diester sweetening agents as well as preparation method and application thereof
  • Aromatic acid DDMP diester sweetening agents as well as preparation method and application thereof
  • Aromatic acid DDMP diester sweetening agents as well as preparation method and application thereof

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preparation example Construction

[0029] The preparation method of above-mentioned aromatic acid DDMP diester comprises the following steps:

[0030] Wherein M is an acylating reagent, specifically

[0031] said Any of benzoyl chloride, m-toluoyl chloride, o-methoxybenzoyl chloride, phenylacetyl chloride, cinnamoyl chloride and p-hydroxycinnamoyl chloride.

[0032] said For benzoic anhydride.

Embodiment 1

[0034] In a 100mL round bottom flask, add 2.88g 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (20mmol) and 40mL of anhydrous dichloromethane, cool To 0 ℃, under the protection of nitrogen, add 4.44g triethylamine (44mmol) and 6.18g benzoyl chloride (44mmol) successively, then rise to room temperature and react for 6h, after the reaction is completed, the reaction solution is washed with water and saturated sodium chloride solution successively 3 times, the organic phase was dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure (in this embodiment and the following embodiments, the vacuum degree of reduced pressure is determined according to actual conditions and needs, as long as the effect of evaporation under reduced pressure is realized That is, it will not affect the realization of the technical solution due to the difference in vacuum), the crude product is separated and purified by silica gel column chromatography, petroleum ether ...

Embodiment 2

[0036] In a 100mL round bottom flask, add 2.88g 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (20mmol) and 40mL anhydrous toluene, cool to - 5°C, under the protection of nitrogen, add 3.56g pyridine (45mmol) and 10.18g benzoic anhydride (45mmol) successively, then rise to room temperature and react for 8h. The organic phase was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The crude product was separated and purified by silica gel column chromatography, eluting with petroleum ether (V): ethyl acetate (V) = 5:1 to obtain 6.23 g of a white solid. It is 2,3-dihydro-3,5-diacetoxy-6-methyl-4H-pyran-4-one, and the yield is 88.49%.

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Abstract

The invention relates to aromatic acid DDMP diester sweetening agents as well as a preparation method and application thereof. According to the technical scheme, 2, 3-dihydro-3, 5-dihydroxyl-6-methyl-4H-pyran-4-one is taken as a raw material, esterification reaction is adopted to prepare six aromatic 2, 3-dihydro-3, 5-diacyloxy-6-methyl-4H-pyran-4-one compounds. The prepared compounds possess excellent storage stability and perfuming stability, when the prepared compounds are added into cigarettes, 2, 3-dihydro-3, 5-dihydroxyl-6-methyl-4H-pyran-4-one is capable of improving oral cavity sweet and moisturizing feel and improving the aftertaste comfort, neutralizing alkaline substances in smoke, generating graceful fragrance, coordinating the graceful fragrance with the smoke fragrance, improving smoke soft and fine degree, improving cigarette aroma quality, enriching smoke fragrance, endowing cigarettes with the characteristics of fruity fragrance, nut fragrance, flowery fragrance or spicy fragrance and the like, and achieving a potential application value.

Description

technical field [0001] The invention belongs to the technical field of synthesis of flavorings for tobacco, in particular to six kinds of 2,3-dihydro-3,5-diacyloxy-6-methyl-4H-pyran-4-one (aromatic acid DDMP diester) , preparation method and application as spice in cigarette. Background technique [0002] 2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one is commonly found in cigarette smoke, Maillard reaction products, sugar cleavage products and natural extracts. Structurally, 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one is similar to maltol, a commonly used caramel aroma substance, and both belong to the class of pyranolones Compounds, most of these compounds with cyclic enolones have a caramel-like aroma; compared with caramel-like aroma substances such as maltol, 2,3-dihydro-3,5-dihydroxy-6-methyl -4H-pyran-4-one has better water solubility, and the "sweetness" presented in the taste is more prominent; it has a significant positive correlation with the "sweetness"...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/32A24B3/12
CPCC07D309/32A24B3/12
Inventor 蔡莉莉杨静陈芝飞赵志伟王保会杨靖席高磊付瑜锋孙志涛李红涛许克静
Owner CHINA TOBACCO HENAN IND
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