24295-03-2

Usage

Uses

Used in Food Industry:
2-Acetylthiazole is used as a flavoring agent in the food industry, particularly for imparting a unique taste to various products. It is used as a food additive in the preparation of 'fragrant' rice, enhancing the overall flavor profile of the dish.
Used in Chemical Synthesis:
2-Acetylthiazole is also utilized in the preparation of triazolothiazoles, chiral alcohols, and in aldol condensation reactions, showcasing its versatility as a chemical intermediate.
Used as an Antioxidant:
In the food industry, 2-Acetylthiazole serves as an antioxidant, helping to preserve the freshness and quality of various food products.
Used as an Appearance Control Agent:
It is also used as an appearance control agent in the food industry, contributing to the visual appeal of certain products.
Taste and Aroma Threshold Values:
2-Acetylthiazole has a taste threshold value of 30 ppm, characterized by a corn chip with a slightly musty background. Its aroma threshold value is detectable at 4 ppb, indicating its potent flavoring capabilities even at low concentrations.

Preparation

2-Acetylthiazole is formed by oxidation of the corresponding carbinol using dichromate.

Synthesis Reference(s)

The Journal of Organic Chemistry, 53, p. 1748, 1988 DOI: 10.1021/jo00243a029

Purification Methods

Check NMR spectrum; if it is not too bad, distil it through an efficient column in a vacuum. The oxime sublimes at 140-145o, m 159o, and when crystallised from H2O has m 163-165.5o. [Erlenmeyer et al. Helv Chim Acta 31 1142 1948, Waisvisz et al. J Am Chem Soc 79 4524 1957, Menasseé et al. Helv Chim Acta 40 554 1957, Beilstein 27 IV 2617.]

InChI:InChI=1/C5H5NOS/c1-4(7)5-6-2-3-8-5/h2-3H,1H3

Upstream product

• 288-47-1 1,3-thiazole 
• 925-90-6 ethylmagnesium bromide 
• 40982-30-7 (±)-1-(thiazol-2-yl)ethanol 
• 14527-42-5 thiazole-2-carboxylic acid ethyl ester 
• 3034-53-5 2-bromo-1,3-thiazole 
• 141-78-6 ethyl acetate 
• 134271-23-1 2-(1,1-Dibromoethyl)thiazole 
• 87830-87-3 Acetic acid 1-thiazol-2-yl-vinyl ester 
• 40610-14-8 2-lithiothiazole 
• 52-90-4 L-Cysteine 
• 50-81-7 ascorbic acid 
• 110-05-4 di-tert-butyl peroxide 
• 201230-82-2 carbon monoxide 
• 3034-55-7 5-bromo-1,3-thiazole 

Downstream Products

• 3292-77-1 2-bromo-1-thiazol-2-yl-ethanone 
• 200440-13-7 2-(1,1-Dimethoxyethyl)thiazole 
• 40982-30-7 (±)-1-(thiazol-2-yl)ethanol 
• 912848-91-0 3-dimethylamino-1-(2-thiazolyl)-2-propen-1-one 
• 157024-10-7 (6R,8R)-6,8-di-O-benzyl-7-deoxy-1,2:3,4-di-O-isopropylidene-8-(thiazol-2-yl)-β-L-threo-D-galacto-octopyranose 
• 910824-85-0 N-cyclohexyl[1-(thiazol-2-yl)ethylidene]amine 
• 1000029-34-4 1-(5-phenylthiazol-2-yl)ethanone 
• 1022944-69-9 3-cyano-2-ethoxy-4-phenyl-7-(thiazol-2-yl)-1,8-naphthyridine 
• 1094497-02-5 (S)-4-nitro-3-phenyl-1-(thiazol-2-yl)butan-1-one 
• 1094497-04-7 (R)-4-nitro-3-phenyl-1-(1,3-thiazol-2-yl)butan-1-one 
• 1202769-68-3 2-(1,3-thiazol-2-yl)but-3-yn-2-ol 
• 306935-40-0 C₇H₄F₃NO₂S 
• 623143-42-0 (1S)-1-(1,3-thiazol-2-yl)ethanamine 
• 623143-43-1 (1R)-1-(thiazol-2-yl)ethanamine 

Relevant academic research and scientific papers

Characteristic flavor formation of thermally processed N-(1-deoxy-α-D-ribulos-1-yl)-glycine: Decisive role of additional amino acids and promotional effect of glyoxal

The role of amino acids and α-dicarbonyls in the flavor formation of Amadori rearrangement product (ARP) during thermal processing was investigated. Comparisons of the volatile compounds and their concentrations when N-(1-deoxy-α-D-ribulos-1-yl)-glycine r

Carbonylative Acetylation of Heterocycles

Herein, a new procedure for the carbonylative acetylation of heterocycles has been developed. In this process, organic peroxide acts as the methyl source. Various heterocycles were transformed into the corresponding methyl heterocyclic ketones in moderate to good yields.

Synthetic method for 2-acetyl thiazole

The invention relates to a synthetic method for 2-acetyl thiazole. The synthetic method comprises the following steps: firstly, preparation of 2-amino thiazole is carried out, namely, toluene, thiourea and chloroacetaldehyde are mixed, a reaction is carried out with stirring at a constant temperature, and 2-amino thiazole is prepared; secondly, preparation of 2-bromo thiazole is carried out, namely, 2-amino thiazole is dissolved in sulfuric acid, cooling is carried out, a sodium nitrite aqueous solution is added drop by drop slowly at a controlled temperature after concentrated nitric acid is added drop by drop, stirring is carried out continuously, a reaction is carried out, the solution after the reaction is added in a mixed solution of sodium bromide and copper sulphate, a bromination reaction is carried out, and 2-bromo thiazole is prepared; thirdly, preparation of 2-acetyl thiazole is carried out, namely, 2-bromo thiazole is added in a butyllithium solution, stirring is carried out, then ethyl acetate is added, a reaction is carried out, and 2-acetyl thiazole is prepared. The acetylation step of 2-bromo thiazole is improved, the reaction raw material ratio and the reaction temperature are optimized, the high yield of the reaction is achieved, safe and reliable operation of the experiment is ensured effectively, and unexpected technical effects are achieved.

Mechanism of formation of sulphur aroma compounds from l-ascorbic acid and l-cysteine during the Maillard reaction

The sulphur aroma compounds produced from a phosphate-buffered solution (pH 8) of l-cysteine and l-, l-[1-13C] or l-[4-13C] ascorbic acid, heated at 140 ± 2 °C for 2 h, were examined by headspace SPME in combination with GC-MS. MS data indicated that C-1 of l-ascorbic acid was not involved in the formation of sulphur aroma compounds. The sulphur aroma compounds formed by reaction of l-ascorbic acid with l-cysteine mainly contained thiophenes, thiazoles and sulphur-containing alicyclic compounds. Among these compounds, 1-butanethiol, diethyl disulphide, 5-ethyl-2-methylthiazole, cis and trans-3,5-dimethyl-1,2,4-trithiolane, thieno[2,3-b]thiophene, thieno[3,2-b]thiophene, cis and trans-3,5-diethyl-1,2,4-trithiolane, 1,2,5,6-tetrathiocane, 2-ethylthieno[2,3-b]thiophene, 2,4,6-trimethyl-1,3,5- trithiane and cyclic octaatomic sulphur (S8) were formed solely by l-cysteine degradation, and the rest by reaction of l-ascorbic acid degradation products, such as hydroxybutanedione, butanedione, acetaldehyde, acetol, pyruvaldehyde and formaldehyde with l-cysteine or its degradation products, such as H2S and NH3. A new reaction pathway from l-ascorbic acid via its degradation products was proposed.

Aroma compounds generated from thermal reaction of l-ascorbic acid with l-cysteine

The reaction of l-ascorbic acid with l-cysteine in heated aqueous solution (141 ± 1 °C) at five different pH values (5.00, 6.00, 7.00, 8.00, or 9.00) for 2 h, resulted in the formation of a complex mixture of aroma volatiles. The volatile compounds generated were analysed by SPME-GC-MS. The results gave 43 aroma compounds. The reaction between l-ascorbic acid and l-cysteine led mainly to the formation of alicyclic sulphur compounds, thiophenes, thienothiophenes, thiophenones, thiazoles and pyrazines, most of which contain sulphur. Many of these volatiles had meaty flavour. The origin of many of the compounds was explained. The studies showed that thienothiophenes and thienones were formed mainly at acidic pH. In contrast, higher pH values could promote the production of thiophenes, thiazoles and pyrazines.

Discovery and SAR of novel 4-thiazolyl-2-phenylaminopyrimidines as potent inhibitors of spleen tyrosine kinase (SYK)

A series of SYK inhibitors based on the phenylamino pyrimidine thiazole lead 4 were prepared and evaluated for biological activity. Lead optimization provided compounds with nanomolar Ki's against SYK and potent inhibition in mast cell degranulation assays.

THIAZOLES USEFUL AS INHIBITORS OF PROTEIN KINASES

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Thiazole, imidazole and oxazole compounds and treatments of disorders associated with protein aging

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Method for treating glaucoma IIB

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