35671-83-1

Basic information

• Product Name: AC-MET-OME
• Synonyms: ACETYL-L-METHIONINE METHYL ESTER;AC-METHIONINE-OME;AC-MET-OME;N-ALPHA-ACETYL-L-METHIONINE METHYL ESTER;N-Acetyl-L-methionine methyl ester;Ac-L-Met-OMe;N-alpha-Actetyl-L-methionine methyl ester;(S)-2-(Acetylamino)-4-(methylthio)butanoic acid methyl ester
• CAS NO: 35671-83-1
• Molecular Formula: C₈H₁₅NO₃S
• Molecular Weight: 205.27
• Product Categories: Amino Acid Derivatives;Amino Acids
• Mol File: 35671-83-1.mol
• Article Data: 10

Chemical Properties

• Melting Point: 96 °C
• Boiling Point: 372.3 °C at 760 mmHg
• Flash Point: 179 °C
• Appearance: /
• Density: 1.113 g/cm³
• Vapor Pressure: 9.71E-06mmHg at 25°C
• Refractive Index: 1.481
• Storage Temp.: -15°C
• Solubility: Chloroform, DMSO
• PKA: 14.55±0.46(Predicted)
• CAS DataBase Reference: AC-MET-OME(CAS DataBase Reference)
• NIST Chemistry Reference: AC-MET-OME(35671-83-1)
• EPA Substance Registry System: AC-MET-OME(35671-83-1)

Safety Data

• Hazardous Substances Data: 35671-83-1(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

InChI:InChI=1/C8H15NO3S/c1-6(10)9-7(4-5-13-3)8(11)12-2/h7H,4-5H2,1-3H3,(H,9,10)/t7-/m0/s1

Upstream product

• 35671-83-1 methyl 2-acetamido-4-methylthiobutanoate 
• 126027-78-9 N-Acetyl-L-methionine sulfoxide methyl ester 
• 59-51-8 DL-methionine 
• 10332-17-9 DL-methionine methyl ester 
• 108-24-7 acetic anhydride 
• 67-56-1 methanol 
• 1115-47-5 N-acetyl-DL-methionine 
• 77-76-9 2,2-dimethoxy-propane 
• 500872-34-4 Fmoc-L-Met-OMe 
• 10332-17-9 Met-OMe 
• 2491-18-1 (S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride 
• 124-41-4 sodium methylate 
• 65-82-7 N-acetyl-l-methionine 

Downstream Products

• 29744-03-4 Ac-L-Met-NHMe 
• 63-68-3 L-methionine 
• 65-82-7 N-acetyl-l-methionine 
• 1527499-55-3 1-acetyl-3-(5-cyclohexyl-1-hydroxypentylidene)-5-(2-(methylthio)ethyl)pyrrolidine-2,4-dione 
• 75-90-1 2,2,2-Trifluoroacetaldehyde 
• 132436-46-5 N-acetyl-L-methionine methyl ester sulfoxide 
• 1115-47-5 N-acetyl-DL-methionine 
• 464-72-2 tetraphenylethane-1,2-diol 

Relevant articles and documents

Mechanism of Buffer Catalysis in the Iodine Oxidation of N-Acetylmethionine Methyl Ester

The iodine oxidation of N-acetylmethionine methyl ester is catalyzed by carboxylic acid buffers.At very low concentrations, the reaction is first order with respect to buffer and follows an iodide dependence that can be described as inverse squared, changing to invers cubed as the iodide concentration is increased.This iodide dependence is observed at all buffer concentrations examined, although the transition from inverse squared to inverse cubed occurs at higher iodide concentrations as the buffer concentration is increasd.As the buffer concentration is increased, the observed rate constants become dependent upon 2 and at "high" buffer (typically > 0.3 M) the reaction again becomes first order with respect to buffer.Broensted coefficients, based on four carboxylic acid buffers, are 1.0 and 1.5 for the first- and second-order terms, respectively.In the reaction catalyzed by acetate, acetic anhydride is produced in an amount equal to the concentraion of sulfide that is oxidized.The data are rationalized in terms of a mechanism involving the rapid formation of an iodosulfonium ion which is attacked by buffer to give an intermadiate O-acylsulfoxide.The O-acylsulfoxide can partition by back-reaction with iodide or by attack of buffer or water at the acyl carbon to give either unhydride or free acid.The βeq for O-acylsulfoxide formation is estimated to be 1.5.Possible transition states for O-acylsulfoxides formation and the possible roles of sulfurane intermediates in these reactions are discussed.

Comparison of liquid chromatography-isotope ratio mass spectrometry (LC/IRMS) and gas chromatography-combustion-isotope ratio mass spectrometry (GC/C/IRMS) for the determination of collagen amino acid δ13C values for palaeodietary and palaeoecological reconstruction

Results are presented of a comparison of the amino acid (AA) δ13C values obtained by gas chromatography-combustion-isotope ratio mass spectrometry (GC/C/IRMS) and liquid chromatography-isotope ratio mass spectrometry (LC/IRMS). Although the primary focus was the compound-specific stable carbon isotope analysis of bone collagen AAs, because of its growing application for palaeodietary and palaeoecological reconstruction, the results are relevant to any field where AA δ13C values are required. We compare LC/IRMS with the most up-to-date GC/C/IRMS method using N-acetyl methyl ester (NACME) AA derivatives. This comparison involves the analysis of standard AAs and hydrolysates of archaeological human bone collagen, which have been previously investigated as N-trifluoroacetyl isopropyl esters (TFA/IP). It was observed that, although GC/C/IRMS analyses required less sample, LC/IRMS permitted the analysis of a wider range of AAs, particularly those not amenable to GC analysis (e.g. arginine). Accordingly, reconstructed bulk δ13C values based on LC/IRMS-derived δ13C values were closer to the EA/IRMS-derived δ13C values than those based on GC/C/IRMS values. The analytical errors for LC/IRMS AA δ13C values were lower than GC/C/IRMS determinations. Inconsistencies in the δ13C values of the TFA/IP derivatives compared with the NACME- and LC/IRMS-derived δ13C values suggest inherent problems with the use of TFA/IP derivatives, resulting from: (i) inefficient sample combustion, and/or (ii) differences in the intra-molecular distribution of δ13C values between AAs, which are manifested by incomplete combustion. Close similarities between the NACME AA δ13C values and the LC/IRMS-derived δ13C values suggest that the TFA/IP derivatives should be abandoned for the natural abundance determinations of AA δ13C values.

Chloroperoxidase-catalyzed oxidation of methionine derivatives

Treatment of N-methoxycarbonyl C-carboxylate ester derivatives of L- and D-methionine and L-ethionine by chloroperoxidase-hydrogen peroxide resulted in oxidation at sulfur to produce the (RS) sulfoxide in moderate to high diastereomeric excess.