92065-73-1

Basic information

• Product Name: 3-Acetylthio-2-methyl propionic acid methyl ester
• Synonyms: 3-Acetylthio-2-methyl propionic acid methyl ester
• CAS NO: 92065-73-1
• Molecular Formula: C7H12O3S
• Molecular Weight: 176.23338
• Mol File: 92065-73-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Acetylthio-2-methyl propionic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Acetylthio-2-methyl propionic acid methyl ester(92065-73-1)
• EPA Substance Registry System: 3-Acetylthio-2-methyl propionic acid methyl ester(92065-73-1)

Safety Data

• Hazardous Substances Data: 92065-73-1(Hazardous Substances Data)

Upstream product

• 507-09-5 thioacetic acid 
• 80-62-6 methacrylic acid methyl ester 
• 3673-79-8 methyl 2,3-dibromoisobutyrate 
• 10387-40-3 potassium thioacetate 
• 67-56-1 methanol 
• 33325-40-5 3-(acetylthio)-2-methylpropanoic acid 
• 86961-07-1 methyl (R)-(+)-3-(acetylthio)-2-methylpropanoate 
• 507-09-5 tiolacetic acid 
• 100-85-6 N-benzyl-trimethylammonium hydroxide 
• 121-44-8 triethylamine 
• 142402-78-6 methyl (2S)-3-hydroxy-2-methyl-3-(methylsulfonyloxy)propanoate 
• 4143-61-7 diethyl diazodicarboxylate 
• 80657-57-4 3-hydroxy-(2S)-methylpropionate 
• 603-35-0 triphenylphosphine 

Downstream Products

• 86961-09-3 (R)-(+)-Methyl 3-mercapto-2-methylpropionate 
• 86961-08-2 methyl (S)-(-)-3-acetyl-thio-2-methylpropanoate 

Relevant articles and documents

Simplified captopril analogues as NDM-1 inhibitors

Captopril is a New Delhi metallo-β-lactamase-1 (NDM-1) inhibitor with an IC50 value of 7.9 μM. It is composed of two units: a 3-mercapto-2-methylpropanoyl fragment and a proline residue. In this study, we synthesized simple amide derivatives of 3-mercapto-2-methylpropanoic acid, and then tested them as NDM-1 inhibitors in order to identify the pharmacophore for NDM-1 inhibition. We found that the lead compound 22 had an IC50 value of 1.0 μM. Further structure simplification provided compounds 31 and 32, which had IC50 values of 15 and 10 μM, respectively. As compound 32 is a clinically used antidote for metal poisoning, it has great potential to be repurposed to treat bacterial infections.

Simplified captopril analogues as NDM-1 inhibitors

Captopril is a New Delhi metallo-β-lactamase-1 (NDM-1) inhibitor with an IC50 value of 7.9 μM. It is composed of two units: a 3-mercapto-2-methylpropanoyl fragment and a proline residue. In this study, we synthesized simple amide derivatives of 3-mercapto-2-methylpropanoic acid, and then tested them as NDM-1 inhibitors in order to identify the pharmacophore for NDM-1 inhibition. We found that the lead compound 22 had an IC50 value of 1.0 μM. Further structure simplification provided compounds 31 and 32, which had IC50 values of 15 and 10 μM, respectively. As compound 32 is a clinically used antidote for metal poisoning, it has great potential to be repurposed to treat bacterial infections.

Effect of the α-methyl substituent on chemoselectivity in esterase-catalyzed hydrolysis of S-acetyl sulfanylalkanoates

(Equation Presented) The isomeric compounds 1 and 3, which differ only in the position of a methyl substituent, give opposite chemoselectivities in an esterase-catalyzed hydrolysis reaction. The esterase was chemoselective for the oxoester in 1, but for the thiol ester group in 3. A high enantioselectivity was observed for both 1 and 3.

Thioglycerol derivatives

A compound of the invention is represented by the formula: STR1 wherein R1 and R2 are the same or different, an acyl group; R3, R4, R6 and R7 are the same or different, hydrogen or an alkyl

Process Conditions for Production of D-β-Acetylthioisobutyric Acid from Methyl DL-β-Acetylthioisobutyrate with the Cells of Pseudomonas putida MR-2068

The process conditions concerned with the production of D-β-acetylthioisobutyric acid were investigated.Methyl DL-β-acetylthioisobutyrate as an enzyme substrate was produced from methyl methacrylate in 96.6percent yield by allowing 1.0 mol of methyl methacrylate to react with 1.6 mol of thioacetic acid at 80 deg C for 6 h.Through the study of hydrolytic reaction of methyl DL-β-acetylthioisobutyrate with the cells of Pseudomonas putida MR-2068, it was found that D-β-acetylthioisobutyric acid having more than 98percent (e. e.) optical purity was obtained when the reaction was done below pH 7.5 and below 50 deg C.For example, 10percent (w/v) methyl DL-β-acetylthioisobutyrate in the reaction mixture was asymmetrically hydrolyzed by 0.2percent (w/v) cells at 45 deg C at pH 7.0 for 18 h to give DAT having 98.2percent (e. e.) optical purity in 49.7percent yield.To prevent the decomposition and racemization of D-β-acetylthioisobutyric acid in the purification process, the use of a thin-film distillation apparatus for a continuous distillation was proposed to be an effective purification method.

Chemical Racemization of Methyl L-β-Acetylthioisobutyrate

Methyl L-β-acetylthioisobutyrate was racemized with 1,8-diazabicyclo--undecene-7 as a catalyst.Methyl methacrylate and thioacetic acid were identified as the intermediates of the reaction.Thioacetic acid was relatively unstable and susceptible to decomposition during the racemization process.The addition of excess methyl methacrylate to the reaction mixture prevented a decrease of the racemate.The racemized ester was confirmed to be usable as a substrate for the enzymatic production of D-β-acetylthioisobutyric acid.

HYDROXYALKYLQUINOLINE ETHER ACIDS AS LEUKOTRIENE ANTAGONISTS

Compounds having the formula I: STR1 are leukotriene antagonists and inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina

Antiviral and Antitumor Structure-Activity Relationship Studies on Tetracyclic Eudistomines

The in vitro antiviral and antitumor activities of (-)-debromoeudistomin K (1a) and 10 structural analogues (1b-1j and 11) were evaluated.The synthesis was accomplished with an intramolecular Pictet-Spengler condensation reaction as the key step.This exam

Screening of Microorganisms Producing D-β-Acetylthioisobutyric Acid from Methyl DL-β-Acetylthioisobutyrate

Microorganisms producing D-β-acetylthioisobutyric acid from methyl DL-β-acetylthioisobutyrate were screened from stock cultures.The D-β-acetylthioisobutyric acid-producing ability was found in 15 strains belonging to the genera Pseudomonas, Agrobacterium, Enterobacter, Cellulomonas, Rhodococcus, Brevibacterium, and Torulopsis.A strain of Pseudomonas fluorescens, IFO 3081, was selected as the best microorganism.The cells having activity (558 units/g of dry cells) could be easily prepared by cultivation at 25 deg C at pH 6.6 for 24 hr in a glucose-containing medium.The D-form of methyl DL-β-acetylthioisobutyrate was selectively hydrolyzed with the cells so that D-β-acetylthioisobutyric acid (97.2percent enantiomeric excess) was produced in a high yield.