10332-17-9

Basic information

• Product Name: methyl methionate
• Synonyms: methyl methionate;methionine methyl ester;(S)-2-Amino-4-(methylthio)butanoic acid methyl ester;L-Methionine methyl;L-Met-OMe;Methionine methyl
• CAS NO: 10332-17-9
• Molecular Formula: C₆H₁₃NO₂S
• Molecular Weight: 163.23792
• EINECS: 233-721-6
• Mol File: 10332-17-9.mol
• Article Data: 44

Chemical Properties

• Melting Point: 147-150 °C
• Boiling Point: 240°Cat760mmHg
• Flash Point: 99°C
• Appearance: /
• Density: 1.094g/cm³
• Vapor Pressure: 0.0388mmHg at 25°C
• Refractive Index: 1.49
• PKA: 6.96±0.35(Predicted)
• CAS DataBase Reference: methyl methionate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl methionate(10332-17-9)
• EPA Substance Registry System: methyl methionate(10332-17-9)

Safety Data

• Hazardous Substances Data: 10332-17-9(Hazardous Substances Data)

Usage

General Description

Methyl methionate, also known as methionine methyl ester, is a chemical compound used in the synthesis of pharmaceuticals, agrochemicals, and food additives. It is derived from the amino acid methionine and is commonly used as a source of sulfur in animal feed. Methyl methionate is also used as a precursor in the production of methionine, which is an essential amino acid for human and animal nutrition. methyl methionate is known for its role in supporting protein synthesis and overall metabolic function in living organisms. It is important in the regulation of various biochemical processes and serves as a key component in the production of numerous essential compounds in the body.

InChI:InChI=1/C6H13NO2S/c1-9-6(8)5(7)3-4-10-2/h5H,3-4,7H2,1-2H3

Upstream product

• 67-56-1 methanol 
• 63-68-3 L-methionine 
• 10332-17-9 DL-methionine methyl ester 
• 1152-62-1 Cbz-Met-OH 
• 77-76-9 2,2-dimethoxy-propane 
• 50903-61-2 N-Boc methionine pentafluorophenol ester 
• 163926-92-9 N-Pent-4-enoyl-L-methionine methyl ester 
• 41442-22-2 L-methionine sodium salt 
• 648910-25-2 N-(3-methyl-2-butenyl)oxycarbonyl-L-methionine methyl ester 
• 500872-34-4 Fmoc-L-Met-OMe 
• 946132-50-9 C₁₈H₂₀N₂O₄S 
• 56762-93-7 methyl (S)-2-(benzyloxycarbonylamino)-4-methylmercaptobutanoate 
• 115481-99-7 (S)-3-benzyloxycarbonyl-4-(2-methylthioethyl)oxazolidin-5-one 
• 2491-18-1 (S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride 

Downstream Products

• 3561-48-6 N-(N-benzyloxycarbonyl-glycyl)-L-methionine 
• 14614-22-3 Z-Ser-Met-OMe 
• 63-68-3 L-methionine 
• 3588-69-0 N-(4-phenylazo-benzoyl)-L-methionine methyl ester 
• 106302-42-5 N-(N-benzyloxycarbonyl-α-L-glutamyl)-L-methionine methyl ester 
• 22838-78-4 (S)-3-Benzyloxycarbonylamino-N-((S)-1-methoxycarbonyl-3-methylsulfanyl-propyl)-succinamic acid benzyl ester 
• 92466-11-0 N-trityl-leucyl-methionine methyl ester 
• 87363-81-3 ^tBOC-Gly-ΔPhe-(S)-Met-OMe 
• 111082-91-8 Z(OMe)-Gly-Met-OMe 
• 78450-66-5 Z(OMe)-Phe-Met-OMe 
• 40290-63-9 Methyl ester of N-t-butyloxycarbonyl-L-phenylalanyl-L-methionine 
• 78816-88-3 (S)-methyl 2-(((S)-2-(benzyloxy)carbonylamino)-3-phenylpropanamido)-4-(methylthio)butanoate 
• 98317-56-7 Tert-butyloxycarbonyltyrosyl-glycyl-glycyl-phenylalanyl-leucyl-methionine Methyl Ester 
• 87218-98-2 Boc-Cys(MBzl)-Met-OMe 

Relevant articles and documents

Efficient synthesis of (S,S)-ethambutol from L-methionine

Starting from readily available amino acid L-methionine, an efficient synthesis of the tuberculostatic agent (S,S)-ethambutol has been developed. The key steps in the synthetic sequence involve: dimerization of methionine methyl ester through oxalyl diamide formation, Raney nickel desulfurization of the terminal thiomethyl groups, and a one-pot exhaustive reduction of the oxalamide and the diester functionalities to afford the desired enantiopure (S,S)-ethambutol in good overall yield.

Photooxidation of Methionine Derivatives by the 4-Carboxybenzophenone Triplet State in Aqueous Solution. Intracomplex Proton Transfer Involving the Amino Group

Oxidation of the triplet state of 4-carboxybenzophenone (CB) by a series of five substituted methionines and three methionine-containing dipeptides was monitored under laser flash photolysis conditions in aqueous solution. Spectral resolution techniques were employed to follow the concentration profiles of the intermediates formed from the quenching events. From these concentration profiles, quantum yields for the intermediates were determined. Branching ratios were evaluated for the decay of the charge-transfer complex by the competing processes of back electron transfer, proton transfer and escape of radical ions. The relative prominence of these processes was discussed in terms of the proton-transfer tendencies of the nominal sulfur-radical-cationic species. A systematic decrease was observed in the quantum yields for the escape of radical ions along with a correlated increase in the proton-transfer yields. The enhanced propensity of the sulfur radical cations to deprotonate is due to deprotonation at the carbons adjacent to the sulfur-cationic site and at the unsubstituted amino groups when present. This scheme was supported by an observed decrease in the yields of dimeric sulfur radical cations with an increase in the electron-withdrawing abilities of the substituents, making the radical-cationic species stronger acids. The involvement of protons on the amino groups was implicated by the correlation of the quantum yields of ketyl radical formation in the photo-chemistry experiments with the rate constants for the reaction of the CB radical anion with the sulfur-containing substrates in pulse radiolysis experiments.

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Using ionic liquid [EMIM][CH3COO] as an enzyme-'friendly' co-solvent for resolution of amino acids

An ionic liquid (IL), 1-ethyl-3-methylimidazolium acetate [EMIM][CH3COO], was used in 0-4.0 M (～60% IL, v/v), as a nonvolatile organic medium for the enzymatic resolution of amino acids. When dl-phenylalanine methyl ester was studied as a model substrate, high enantiomeric excesses (ee) of l-amino acid were obtained in all ionic concentrations; however, lower yields were observed at high IL concentrations. This IL is more enzyme-'friendly' than the hydrophilic organic solvent acetonitrile and those ILs containing chaotropic anions (such as [EMIM][OTs]). Among three proteases and two lipases investigated, lyophilized Bacillus licheniformis protease exhibited the best enantioselectivity and activity. Highly enantioselective resolutions were also produced for several other amino acids in 2.0 M IL. Interestingly, high ee were also found in deuterium oxide (D2O) rather than in ordinary water, and a further enhancement was achieved with the co-existence of [EMIM][CH3COO]. The heavy water effect was explained in terms of protein stabilization by D2O. The secondary structural changes of enzyme in various media were interpreted by the second derivatives of FT-IR spectra.

Design, synthesis and evaluation of novel indole derivatives as AKT inhibitors

Herein, we describe the discovery and synthesis of a new series of 1,2,4,7-tetra-substituted indole derivatives as novel AKT inhibitors by optimization of a weak hit methyl 4-(2-aminoethoxy)-1H-indole-2-carboxylate (1). Both representative compounds 6a and 6o exhibited the most potent inhibitory activities against AKT1, with inhibition rates of 72.5% and 78.6%, respectively, at concentrations of 10 nM. In addition, compounds 6a and 6o also potently inhibited the phosphorylation of the downstream GSK3 protein and displayed slightly better anti-proliferative activities in a prostate cancer cell line.

Discovery of γ-Lactam alkaloid derivatives as potential fungicidal agents targeting steroid biosynthesis

Biological control of plant pathogens is considered as one of the green and effective technologies using beneficial microorganisms or microbial secondary metabolites against plant diseases, and so microbial natural products have played important roles in the research and development of new and green agrochemicals. To explore the potential applications for natural γ-lactam alkaloids and their derivatives, 26 γ-lactams that have flexible substituent patterns were synthesized and characterized, and their in vitro antifungal activities against eight kinds of plant pathogens belonging to oomycetes, basidiomycetes, and deuteromycetes were fully evaluated. In addition, the high potential compounds were further tested using an in vivo assay against Phytophthora blight of pepper to verify a practical application for controlling oomycete diseases. The potential modes of action for compound D1 against Phytophthora capsici were also investigated using microscopic technology (optical microscopy, scanning electron microscopy, and transmission electron microscopy) and label-free quantitative proteomics analysis. The results demonstrated that compound D1 may be a potential novel fungicidal agent against oomycete diseases (EC50 = 4.9748 μg·mL-1 for P. capsici and EC50 = 5.1602 μg·mL-1 for Pythium aphanidermatum) that can act on steroid biosynthesis, which can provide a certain theoretical basis for the development of natural lactam derivatives as potential antifungal agents.

N-Pyrazinoyl substituted amino acids as potential antimycobacterial agents-the synthesis and biological evaluation of enantiomers

Tuberculosis is an infectious disease caused by Mycobacterium tuberculosis (Mtb), each year causing millions of deaths. In this article, we present the synthesis and biological evaluations of new potential antimycobacterial compounds containing a fragment of the first-line antitubercular drug pyrazinamide (PZA), coupled with methyl or ethyl esters of selected amino acids. The antimicrobial activity was evaluated on a variety of (myco)bacterial strains, including Mtb H37Ra, M. smegmatis, M. aurum, Staphylococcus aureus, Pseudomonas aeruginosa, and fungal strains, including Candida albicans and Aspergillus flavus. Emphasis was placed on the comparison of enantiomer activities. None of the synthesized compounds showed any significant activity against fungal strains, and their antibacterial activities were also low, the best minimum inhibitory concentration (MIC) value was 31.25 μM. However, several compounds presented high activity against Mtb. Overall, higher activity was seen in derivatives containing l-amino acids. Similarly, the activity seems tied to the more lipophilic compounds. The most active derivative contained phenylglycine moiety (PC-d/l-Pgl-Me, MIC 1.95 μg/mL). All active compounds possessed low cytotoxicity and good selectivity towards Mtb. To the best of our knowledge, this is the first study comparing the activities of the d- and l-amino acid derivatives of pyrazinamide as potential antimycobacterial compounds.