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Thiazole compound characterized by bean aroma and preparation method thereof

A technology for compounds and thiazoles, which is applied in the field of extraction and separation of 4-methyl-5-R-thiazole, a characteristic compound with bean aroma, can solve the problem of separation of thiol aroma components, unknown structure, and low content that have not been reported in the literature. and other problems, to achieve the effect of good application prospect, simple process and convenient operation

Active Publication Date: 2016-02-24
BOTON SHANGHAI BIOLOGICAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] 4-Methyl-5-(β-hydroxyethyl)-thiazole is commonly used as a chemically synthesized food flavor. During different processing processes such as preparation and purification, a small amount of different impurities that cause aroma are produced to present a nutty bean aroma, Milk aroma, eggy smell, meat aroma, these trace aroma components are small in content and unknown in structure, so it is difficult to be directly detected and identified by gas chromatography-mass spectrometry GC-MS. For the separation and identification of these aroma-causing impurities in mercaptans It has always been a hot spot in the field of fragrance research. So far, there has been no literature report on the separation of this type of aromatizing component in mercaptans, let alone the chemical structure of this aromatizing component in mercaptans.

Method used

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  • Thiazole compound characterized by bean aroma and preparation method thereof
  • Thiazole compound characterized by bean aroma and preparation method thereof
  • Thiazole compound characterized by bean aroma and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Embodiment 1: the extraction and separation of 4-methyl-5-(β-formyloxyethyl)-thiazole in mercaptan comprises the following steps:

[0032] The molecular formula of 4-methyl-5-(β-formyloxyethyl)-thiazole is

[0033] Step 1, raw material extraction:

[0034] Take 750g of bean flavor flavor 4-methyl-5-(β-hydroxyethyl)-thiazole fragrance sample, add 3750g of ultrapure water to dilute, extract 3 times with redistilled isopropyl acetate, dilute the solution with isopropyl acetate The volume ratio is 1:2, the isopropyl acetate layer is combined, and concentrated under reduced pressure to obtain the bean fragrance sample A;

[0035] Step 2, separation and purification:

[0036] Add dichloromethane to dissolve the bean fragrance sample A obtained in step 1, mix the sample with silica gel at a mass ratio of 1:1.5, evaporate the solvent, and then load the sample on a silica gel chromatography column for ordinary silica gel column chromatography separation.

[0037] Use n-hexa...

Embodiment 2

[0039] Embodiment 2: the extraction and separation of 4-methyl-5-(β-acetoxyethyl)-thiazole in mercaptans comprises the following steps:

[0040] The molecular formula of 4-methyl-5-(β-acetoxyethyl)-thiazole is

[0041] Step 1, raw material extraction:

[0042] Get bean flavor flavor 4-methyl-5-(β-hydroxyethyl)-thiazole flavor sample 750g, add ultrapure water 375g to dilute, extract 4 times with the sherwood oil of redistillation, the volume ratio of diluent and sherwood oil is 1:1, the petroleum ether layer was combined, and concentrated under reduced pressure to obtain the bean fragrance sample A;

[0043] Step 2, separation and purification:

[0044] Add appropriate amount of dichloromethane to dissolve the bean flavor sample A obtained in step 1,

[0045]Mix the sample with silica gel at a mass ratio of 1:2, evaporate the solvent, and then load the sample on a silica gel chromatography column for ordinary silica gel column chromatography. Use n-hexane-ethyl acetate sy...

Embodiment 3

[0047] Embodiment 3: the extraction and separation of 4-methyl-5-(2-ketopropionyl)-thiazole in mercaptan comprises the following steps:

[0048] The molecular formula of 4-methyl-5-(2-ketopropionyl)-thiazole is

[0049] Step 1, raw material extraction:

[0050] Get bean flavor flavor 4-methyl-5-(β-hydroxyethyl)-thiazole fragrance sample 750g, add ultrapure water and dilute to 1500ml, extract 4 times with the sherwood oil that reclaims, the volume ratio of diluent and sherwood oil is 1:2, combine the petroleum ether layers, and concentrate under reduced pressure to obtain the bean fragrance sample A;

[0051] Step 2, separation and purification:

[0052] Add appropriate amount of dichloromethane to dissolve the bean flavor sample A obtained in step 1,

[0053] Mix the sample with silica gel at a mass ratio of 1:1.5, evaporate the solvent, and then load the sample on a silica gel chromatography column for ordinary silica gel column chromatography separation. Use n-hexane-e...

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Abstract

The invention discloses a thiazole compound characterized by a bean aroma and a preparation method thereof. The thiazole compound has a molecular structural formula shown in the specification, wherein R is formyloxyethyl, acetoxyethyl, formyloxymethyl, acetoxymethyl, 2-ketopropionyl or 2-hydroxypropionyl. The preparation method of the thiazole compound comprises the following steps: firstly, diluting a mercaptan sample, performing extraction with redistilled petroleum ether, combining petroleum ether layers obtained after extraction of each time, and performing vacuum concentration to obtain a bean aroma sample A; secondly, adding dichloromethane to dissolve the bean aroma sample A, volatilizing the dissolvent, and carrying out sample loading on a silica gel chromatography column to perform common silica gel column chromatographic separation; thirdly, collecting part of eluent in a selected range according to polarity from small to large by taking an n-hexane-ethyl acetate system as a mobile phase, combining high-purity fractions according to an Rf value, and combining all eluted fractions according to aromas after concentration to obtain a part sample B containing a bean aroma component; and finally, purifying the part sample B containing the bean aroma component, and performing concentration and reduced-pressure drying to obtain a target product.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, and relates to a preparation method of 4-methyl-5-R-thiazole, a characteristic compound of bean flavor and aroma, especially refers to the extraction and separation of 4-methyl-5-R-thiazole, a characteristic compound of bean flavor and aroma, from mercaptan spices. 5-R-thiazole method. Background technique [0002] The chemical name of sulfur thiazole: 4-methyl-5-(β-hydroxyethyl)-thiazole, referred to as thiol; the English name is 4-Methyl-5-beta-hydroxyethylthiazole referred to as MHT. The FEMA number is 3204. Colorless to light yellow viscous oily liquid, the color becomes dark after long storage. The boiling points are: 135°C / 933.3Pa, 123~124°C / 399.9Pa, 103°C / 133.3Pa. The refractive index is: n D 20 =1.5470, very soluble in water, soluble in ethanol, ether, benzene and chloroform, has an unpleasant smell of thiazole compounds at higher concentrations, but has a pleasant fragranc...

Claims

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Application Information

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IPC IPC(8): C07D277/24
CPCC07D277/24
Inventor 李斌陈亮
Owner BOTON SHANGHAI BIOLOGICAL TECH CO LTD