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Novel flavor compound and preparation method, application and composition thereof

A technology of compounds and compositions, applied in the field of new fragrance compounds

Active Publication Date: 2010-02-10
XIAMEN OMIC BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the theory of predicting the aroma characteristics of a new compound through the molecular structure of organic compounds has not fully explained the internal relationship between them, we can know that the number of carbon atoms, unsaturation, functional groups, substituents, Factors of isomerization have a great influence on the aroma of fragrance compounds

Method used

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  • Novel flavor compound and preparation method, application and composition thereof
  • Novel flavor compound and preparation method, application and composition thereof
  • Novel flavor compound and preparation method, application and composition thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1: Synthesis of 3-hydroxy-6-phenyl-3,5-hexadien-2-one

[0025] Mix 100g of cinnamaldehyde and 286g of hydroxyacetone at room temperature to obtain a mixture of cinnamaldehyde and hydroxyacetone; add 63g of 15% hydrochloric acid into the reaction flask, raise the temperature to 50°C, and then add the above cinnamon dropwise under stirring at a constant rate within 2h A mixture of aldehyde and hydroxyacetone, keep it for 2 hours after dripping;

[0026] Then, 110 g of water was added to the reaction solution, the temperature was raised to 82° C. and the reaction was continued for 2 h; after the reaction, the product was filtered while hot and recrystallized with ethyl acetate to obtain 39.4 g of white crystals. After testing, its melting point is 127.8-128.1°C; the yield is 27.7%.

[0027] 1 H NMR(CDCl 3 , 400MHz): d 2.45 (s, 3H), 6.39 (d, J = 11.2 Hz, 1H), 6.84 (d, J = 12 Hz, 1H), 6.86 (s, 1H), 7.28-7.34 (m, 2H) , 7.35-7.39 (m, 1H), 7.52-7.54 (m, 2H) ppm;

[0028] 13 C...

Embodiment 2

[0030] Example 2: Olfactory evaluation of pure 3-hydroxy-6-phenyl-3,5-hexadien-2-one

[0031] The olfactory evaluation of pure 3-hydroxy-6-phenyl-3,5-hexadien-2-one was completed by an evaluation team composed of several professionals. The compound has a pure and herb-like aroma, with tobacco and bean aromas aroma.

Embodiment 3

[0032] Example 3: The olfactory evaluation of 3-hydroxy-6-phenyl-3,5-hexadien-2-one in the composition

[0033] Component

Test group 1

(%weight ratio)

Test group 2

(%weight ratio)

Test group 3

(%weight ratio)

Ethanol

5％

2％

2.5％

[0034] Squalane

50％

40％

60％

Glyceryl triisocaprylate

20％

25％

20％

Hydroxyethyl cellulose

20％

23％

17.5％

3-hydroxy-6-phenyl-3,5-

Hexadiene-2-one

5％

10％

0％

Total

100％

100％

100％

[0035] Squalane, glyceryl triisocaprylate and hydroxyethyl cellulose can all be purchased directly from the market.

[0036] Test group 1 and 2 had a light herb-like aroma with tobacco and bean aroma, while test group 3 had no such aroma. In addition, the evaluation team conducted T test on the composition of test group 1, test group 2 and test group 3 in an open environment. 0h , T 72 , T 288h The olfactory evaluation results show that the intensity of the fragrance will decrease with time, but the natu...

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Abstract

The invention discloses a novel diketone flavor compound and a preparation method, composition and application thereof. The preparation method comprises the following steps: mixing cinnamic aldehyde and hydroxyacetone under normal temperature and obtaining mixed liquor of the cinnamic aldehyde and the hydroxyacetone; adding 10-30% of hydrochloric acid into a reaction bottle, raising the temperature to 30-60 DEG C, then dropwise adding the mixed liquor of the cinnamic aldehyde and the hydroxyacetone at constant speed within 1-3h while stirring and keeping maintaining for 1-3h after dropping; adding water into the reaction solution and keeping reacting for 1-3h after raising the temperature to 75-85 DEG C; filtering the reactant while the reactant is still hot after reaction to obtain a product, and recrystallizing the product with ethyl acetate to obtain white crystals. The compound has pure and full-bodied fragrance like the fragrance of medicinal herbs, tobaccos and beans, and can beused in such products as perfumes, candles, paints, cleaning products or air fresheners.

Description

Technical field [0001] The present invention relates to a novel fragrance compound that can be used as a fragrance, its preparation method, application and composition, and in particular to a diketone compound, its preparation method, application and composition. Background technique [0002] Ketone compounds occupy an important position in the perfume industry, and ketone perfumes account for about 15% of the total number of perfumes. Aromatic ketone compounds are commonly used spices. C 7 -C 12 The low-carbon fatty ketones can be used directly as spices due to their strong and pleasant smell. While C 3 -C 6 The low-carbon fatty ketones have a weak aroma and are rarely used directly as spices, but due to C 3 -C 6 The unique structure of diketone can be used in food. For example, due to its creamy fragrance, diacetyl can be used in daily fragrances such as lavender, iris, and sandalwood. The main purpose is to prepare cream, cheese, chocolate, cocoa, honey, wine, tobacco and o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/217C07C45/74C11B9/00A61Q13/00C11C5/00C09D7/12C11D9/44A61L9/01A61L101/32
Inventor 王少培黄志强
Owner XIAMEN OMIC BIOTECH CO LTD
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