97101-46-7

Basic information

• Product Name: methyl 3-(acetylthio)-2-methyl-propanoate
• Synonyms: methyl 3-(acetylthio)-2-methyl-propanoate
• CAS NO: 97101-46-7
• Molecular Formula: C₇H₁₂O₃S
• Molecular Weight: 176.23
• EINECS: 411-040-7
• Mol File: 97101-46-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 102-103 °C
• Appearance: /
• Density: 1.108±0.06 g/cm3(Predicted)
• CAS DataBase Reference: methyl 3-(acetylthio)-2-methyl-propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-(acetylthio)-2-methyl-propanoate(97101-46-7)
• EPA Substance Registry System: methyl 3-(acetylthio)-2-methyl-propanoate(97101-46-7)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-43-50/53
• Safety Statements: 24-37-60-61
• Hazardous Substances Data: 97101-46-7(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 33325-40-5 3-(acetylthio)-2-methylpropanoic acid 
• 100-85-6 N-benzyl-trimethylammonium hydroxide 
• 80-62-6 methacrylic acid methyl ester 
• 507-09-5 tiolacetic acid 
• 86961-07-1 methyl (R)-(+)-3-(acetylthio)-2-methylpropanoate 
• 3673-79-8 methyl 2,3-dibromoisobutyrate 
• 10387-40-3 potassium thioacetate 
• 507-09-5 thioacetic acid 

Downstream Products

• 86961-07-1 methyl (R)-(+)-3-(acetylthio)-2-methylpropanoate 
• 76497-39-7 (2S)-3-acetylthio-2-methylpropionic acid 
• 4131-76-4 methyl 3-mercapto-2-methyl-propionate 
• 86961-09-3 (R)-(+)-Methyl 3-mercapto-2-methylpropionate 
• 86961-08-2 methyl (S)-(-)-3-acetyl-thio-2-methylpropanoate 
• 86961-10-6 (S)-Methyl 3-mercapto-2-methylpropionate 

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.

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.

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.