656-53-1

Basic information

• Product Name: 4-Methyl-5-thiazolylethyl acetate
• Synonyms: 4-Methyl-5-thiazolylethyl acetate, Sulfurol acetate;4-Methyl-5-(2-acetoxyethyl)thiazole-4-Methyl-5-thiazoleethanol acetate;2-(4-Methyl-1,3-thiazol-5-yl)ethyl acetate;4-Methyl-5-thiazolylethyl acetate ,99%;4-Methyl-5-thiazolylethyl acetate >=98.0%;Acetic Acid 2-(4-Methyl-5-thiazolyl)ethyl Ester 5-(2-Acetoxyethyl)-4-methylthiazole;4-Methyl-5-(2-hydroxyethyl)thiazoleacetate;4-methyl-5-thiazoleethanoacetate(ester)
• CAS NO: 656-53-1
• Molecular Formula: C₈H₁₁NO₂S
• Molecular Weight: 185.24
• EINECS: 211-515-7
• Product Categories: thiazole Flavor;Building Blocks;C8 to C9;Chemical Synthesis;Heterocyclic Building Blocks;Thiazoles;Heterocyclic Compounds
• Mol File: 656-53-1.mol

Chemical Properties

• Melting Point: 112 °C
• Boiling Point: 117-118 °C6 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear brown/Liquid
• Density: 1.147 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00774mmHg at 25°C
• Refractive Index: n20/D 1.51(lit.)
• Storage Temp.: 2-8°C
• PKA: 3.26±0.10(Predicted)
• CAS DataBase Reference: 4-Methyl-5-thiazolylethyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methyl-5-thiazolylethyl acetate(656-53-1)
• EPA Substance Registry System: 4-Methyl-5-thiazolylethyl acetate(656-53-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25
• RIDADR: UN 3334
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 656-53-1(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
4-Methyl-5-thiazolylethyl acetate is used as a flavoring agent for imparting beeflike process flavor to various food products. Its contribution to the aroma characteristics is assessed through gas chromatography-mass spectrometry and partial least squares regression.
Used in Biological Studies:
4-Methyl-5-thiazolylethyl acetate is utilized in research for studying the role of oxidized tallow in the development of aroma characteristics in beeflike process flavors. This helps in understanding the chemical composition and sensory properties of food products.

Preparation

From 2-methylthio-4-methyl-5-(2-acetohxyethyl)-thiazole and AlHg; by dehydrogenation with sulfur at 130°C of the β-acetyl derivative of 4-methyl-5-(β-hydroxyethyl)-3-thiazoline

InChI:InChI=1/C8H11NO2S/c1-6-7(12-5-9-6)3-4-8(10)11-2/h5H,3-4H2,1-2H3

Upstream product

• 760210-61-5 1-acetoxy-2-(2-chloro-4-methyl-thiazol-5-yl)-ethane 
• 98960-04-4 1-acetoxy-2-(4-methyl-2-methylsulfanyl-thiazol-5-yl)-ethane 
• 77287-34-4 formamide 
• 13051-49-5 5-Acetoxy-3-chloropentan-2-one 
• 115-08-2 thiocarboxamide 
• 14066-76-3 2-mercapto-4-methyl-5-(β-acetoxyethyl)thiazole 
• 69243-00-1 2-(2-amino-4-methylthiazol-5-yl)ethyl acetate 
• 137-00-8 5-hydroxyethyl-4-methylthiazole 
• 75-36-5 acetyl chloride 
• 412307-97-2 5-(2-acetoxy-ethyl)-4-methyl-3H-thiazol-2-one 
• 64-17-5 ethanol 
• 98426-41-6 1-acetoxy-2-(4-methyl-2,5-dihydro-thiazol-5-yl)-ethane 
• 108-24-7 acetic anhydride 

Downstream Products

• 1579941-84-6 (E)-2-(4-methyl-2-styrylthiazol-5-yl)ethyl acetate 
• 100724-70-7 2-hydroxy-4-nitro-benzoic acid-[2-(4-methyl-thiazol-5-yl)-ethyl ester] 
• 100795-90-2 4-amino-2-hydroxy-benzoic acid-[2-(4-methyl-thiazol-5-yl)-ethyl ester] 
• 109311-81-1 5-(2-acetoxy-ethyl)-4-methyl-3-(4-nitro-benzyl)-thiazolium; bromide 
• 137-00-8 5-hydroxyethyl-4-methylthiazole 

Relevant articles and documents

Preparation method of 4-methyl-5-(2-acetoxyethyl) thiazole

The invention relates to a preparation method of 4-methyl-5-(2-acetoxyethyl) thiazole, and discloses a preparation method of 4-methyl-5-(2-acetoxyethyl) thiazole, the 4-methyl-5-(2-acetoxyethyl) thiazole is obtained by reaction of 3-halogenated-5-acetoxy-2-pentanone and thioformamide, and the reaction takes SBA-15 molecular sieve loaded ionic liquid as a catalyst. The catalyst not only improves the reaction yield, but also improves the product purity.

Synthetic method of thiazoles (by machine translation)

4 - Acetoxy 3 - acetyl -3 - chloropropyl acetate is hydrolyzed under acidic conditions to prepare 4 -mercapto -2 - methyl -2 - (β - acetoxyethyl)-thiazole; the step of preparing -2 - methyl -2 - (β - acetoxyethyl)-thiazole with 3 - methyl -3 - (β - acetoxyethyl)-thiazole under acidic condition is carried out under an acidic condition by adding an oxidizing agent under an acidic condition in 3 -chloro -3 -methyl 2 - (β - acetoxyethyl)-thiazole in an acidic condition under an acidic condition by adding 4 - an oxidizing agent under an acidic condition; and a -5 - method -5 - for synthesizing thiazoles -4 - and -5 -mercapto 2 -methyl-ethyl)-thiazole in an acidic condition by adding an -5 - oxidizing agent under an -5 - 4 - acidic condition; and the method comprises the following steps: preparing -4 -4 - ethyl acetoxyethyl)-thiazole. The synthesis method is mild in overall reaction condition, simple in post-treatment and suitable for pilot scale test and industrial production. (by machine translation)

Synthesis of [thiazolium-2,2′-14C2]-SAR97276A from [14C]-thiourea

[thiazolium-2,2′-14C2]-SAR97276A, a bis(thiazolium) antimalarial development candidate, was synthesized from [ 14C]-thiourea with an overall radiochemical yield of 15%. The synthetic route involves a modified procedure for the synthesis of [ 14C]-sulfurol, also a key intermediate in thiamine synthesis, which was developed due to unlabelled chemistry proving irreproducible with the radiolabelled substrate. Copyright

C2, C5, and C4 azole N-oxide direct arylation including room-temperature reactions

The N-oxide group imparts a dramatic increase in reactivity at all positions of the azole ring of thiazoles and imidazoles and changes the weak bias for C5 > C2 arylation to a reliable C2 > C5 > C4 reactivity profile. Use of this cross-coupling strategy enables high yielding and room-temperature C2 arylations, mild reactions at C5, and the first examples of C4 arylation-providing a unique opportunity for exhaustive functionalization of the azole core with complete control of regioselectivity. A correlation of reactivity with the relative contributions of each carbon atom to the HOMO is observed and discussed. Copyright

Synthesis, in vitro and in vivo activity of thiamine antagonist transketolase inhibitors

Tumor cells extensively utilize the pentose phosphate pathway for the synthesis of ribose. Transketolase is a key enzyme in this pathway and has been suggested as a target for inhibition in the treatment of cancer. In a pharmacodynamic study, nude mice with xenografted HCT-116 tumors were dosed with 1 ('N3′-pyridyl thiamine'; 3-(6-methyl-2-amino-pyridin-3-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-thiazol-3-ium chloride hydrochloride), an analog of thiamine, the co-factor of transketolase. Transketolase activity was almost completely suppressed in blood, spleen, and tumor cells, but there was little effect on the activity of the other thiamine-utilizing enzymes α-ketoglutarate dehydrogenase or glucose-6-phosphate dehydrogenase. Synthesis and SAR of transketolase inhibitors is described.