3226-65-1

Basic information

• Product Name: L-METHIONINE SULFOXIDE
• Synonyms: METHIONINE(O)-OH;L-METHIONINE SULFOXIDE;L-METHIONINE SULPHOXIDE;L-METHIONINE-DL-SULFOXIDE;L-LOBAMINE SULFOXIDE;L-BANTHIONINE SULFOXIDE;L-2-AMINO-4-[METHYLSULFINYL]BUTANOIC ACID;H-MET(O)-OH
• CAS NO: 3226-65-1
• Molecular Formula: C₅H₁₁NO₃S
• Molecular Weight: 165.21
• EINECS: 221-758-0
• Product Categories: Amino Acids 13C, 2H, 15N;Amino Acids & Derivatives;Sulfur & Selenium Compounds
• Mol File: 3226-65-1.mol

Chemical Properties

• Melting Point: 234-235°C
• Boiling Point: 434.3 °C at 760 mmHg
• Flash Point: 216.4 °C
• Appearance: White/Powder
• Density: 1.385 g/cm³
• Storage Temp.: 2-8°C
• Solubility: Aqueous Acid (Slightly), Water (Slightly)
• PKA: 2.14±0.10(Predicted)
• Stability: Temperature Sensitive, Hygroscopic
• BRN: 4129939
• CAS DataBase Reference: L-METHIONINE SULFOXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: L-METHIONINE SULFOXIDE(3226-65-1)
• EPA Substance Registry System: L-METHIONINE SULFOXIDE(3226-65-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 3226-65-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
L-Methionine sulfoxide is used as an intermediate for the synthesis of L-Methionine sulfoximine, which is an essential component in the development of certain pharmaceutical products. Its crystalline nature allows for efficient reactions and the creation of valuable compounds with potential therapeutic applications.
Used in Chemical Synthesis:
L-Methionine sulfoxide is utilized as a key intermediate in the synthesis of various acyclic amino carboxylic acids, contributing to the development of new chemical compounds with diverse applications across different industries.

Biochem/physiol Actions

L-Methionine sulfoxide, a structural analog of glutamate, may be used as a substrate to study the specificity and kinetics of various methionine sulfoxide reductase(s).

InChI:InChI=1/C18H28O3S.C5H11NO2S/c1-3-4-5-6-7-8-11-22(19)15(2)12-16-9-10-17-18(13-16)21-14-20-17;1-9-3-2-4(6)5(7)8/h9-10,13,15H,3-8,11-12,14H2,1-2H3;4H,2-3,6H2,1H3,(H,7,8)/t;4-/m.0/s1

Upstream product

• 63-68-3 L-methionine 
• 110815-41-3 trans-5-chloro-6-hydroperoxy-5,6-dihydrothymine 
• 64-18-6 formic acid 
• 7722-84-1 dihydrogen peroxide 
• 7647-01-0 hydrogenchloride 
• 7553-56-2 iodine 
• 13907-45-4 chromate(VI) ion 
• 1207162-72-8 tiglicamide C 
• 108646-71-5 (2S)-2-(acetylamino)-4-(methylsulfinyl)butyric acid 
• 59-51-8 DL-methionine 
• 31418-44-7 methiononitrile sulfate 
• 64-19-7 acetic acid 
• 14486-03-4 N-L-methionyl-glycine 
• 3061-96-9 L-methionyl-L-alanine 

Downstream Products

• 1695-02-9 N-(2,4-dinitro-phenyl)-methionine S-oxide 
• 7314-32-1 L-methionine sulfone 
• 2075-32-3 trans-5-chloro-6-hydroxy-5,6-dihydrothymine 
• 1492-24-6 L-2-aminobutyric acid 
• 63-68-3 L-methionine 
• 108646-71-5 (2S)-2-(acetylamino)-4-(methylsulfinyl)butyric acid 
• 56-84-8 L-Aspartic acid 
• 14857-77-3 L-homocysteic acid 
• 146983-84-8 (S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-methanesulfinyl-butyric acid methyl ester 
• 838-07-3 5-methyldeoxycytidine 
• 3054-52-2 N-benzoyl L-methionine sulphoxide 
• 23631-84-7 (S_CS_S)-L-methionine sulfoxide 
• 59-51-8 DL-methionine 
• 820-10-0 DL-methionine sulfone 

Relevant articles and documents

Structural studies on the stereoisomerism of a natural dye miraxanthin I

The chemical structure of a yellow dye present in Mirabilis jalapa L., miraxanthin I, was characterized by NMR spectroscopy. The extract of M. jalapa was analysed by a high-performance liquid chromatographic system (LC-DAD-FL-ESI-MS/MS) and the presence of miraxanthin I among other betaxanthins was confirmed. This dye was synthesized from previously generated methionine-betaxanthin by oxidation with 10% H2O2. The E/Z stereoisomers of miraxanthin I were found by NMR analysis to occur in a 50?:?33?:?10?:?7 ratio in aqueous solution (7E,9E?:?7Z,9E?:?7E,9Z?:?7Z,9Z configurations, respectively). Comparison of NMR data with chemical shifts obtained from quantum chemical calculations strongly suggests the presence of intramolecular hydrogen bonds which may favour a more rigid structure of the dye. This explains the highest fluorescence quantum yield among betaxanthins. The observed changes in the 1H NMR spectra during the measurements indicate on miraxanthin I hydrolysis for which a mechanism is proposed. The first step during the hydrolysis process is protonation of the nitrogen atom within the central bridge bond system which is observed in the ZE stereoisomer by NMR.

Thiabendazole-based Rh(III) and Ir(III) biscyclometallated complexes with mitochondria-targeted anticancer activity and metal-sensitive photodynamic activity

Two pairs of Rh(III) and Ir(III) biscyclometallated complexes with thiabendazole (L1), named [Ir-a]Cl and [Rh-a]Cl, and N-benzyl-thiabendazole (L2), named [Ir-b]Cl and [Rh-b]Cl, have been designed and synthesized to explore the photophysical and biological effects that arise from changing both the metal center and the ancillary ligand. In the dark, the four metal complexes exhibit greater cytotoxicity than cisplatin against human colon (SW480) and human lung (A549) adenocarcinoma cell lines. Moreover, the pair of complexes bearing the ligand L2 is markedly more cytotoxic and present higher uptake values than complexes with L1, thereby their biological properties were studied further to determine their mechanism of action. Interestingly, in spite of the different metal center both the [Ir-b]Cl and [Rh-b]Cl complexes are responsible for the loss of mitochondrial functionality and the activation of apoptotic cell death pathways. Moreover, the photodynamic activity of the four complexes, [Ir-a,b]Cl and [Rh-a,b]Cl, was tested using visible blue light (460 nm) under soft irradiation conditions (20 min, 5.5 mW cm?2). While the Rh complexes are not photopotentiated, the phototoxicity index (IC50 non-irradiated/IC50 irradiated) of [Ir-a]Cl and [Ir-b]Cl complexes was 15.8 and 3.6, respectively. We also demonstrate that only the Ir derivatives are capable of photocatalyzing the oxidation of S-containing L-amino acids under blue light irradiation, [Ir-a]Cl being more active than [Ir-b]Cl, which provides a reasonable mechanism for their biological action (oxidative stress could be selectively promoted through a photocatalytic action) upon irradiation. This different PDT behaviour depending on the metal center and the ancillary substituent may be useful for future rational design of metal-based photosensitizers.

Diastereomers of Methionine S-Oxide in the Hinge-Ligament Proteins of Molluscan Bivalve Species

The diastereomer ratio was analyzed on methionine S-oxide residues formed by in vivo posttranslational oxidation of methionine residues in a protein.The hinge-ligament protein of molluscan bivalves is distinct from usual proteins in containing a large amount of methionine S-oxide.The methionine S-oxide was released from the protein by proteolytic digestions and was found to be a mixture of approximately equall amounts of two diastereomers, (5S)- and (5R)-L-methionine S-oxide.

Type I Photosensitized Oxidation of Methionine?

Methionine (Met) is an essential sulfur-containing amino acid, sensitive to oxidation. The oxidation of Met can occur by numerous pathways, including enzymatic modifications and oxidative stress, being able to cause relevant alterations in protein functio

Kinetics and mechanism of the oxidation of DL-methionine by tetrakis(pyridine)silver dichromate

The oxidation of methionine by tetrakis(pyridine)silver dichromate in dimethyl sulphoxide leads to the formation of corresponding sulphoxide. The reaction is of first order with respect to tetrakis(pyridine)silver dichromate. Michaelis-Menten type kinetic

Modulation of amyloid fibrillation of bovine β-lactoglobulin by selective methionine oxidation

Deposition of oxidation-modified proteins during normal aging and oxidative stress are directly associated with systemic amyloidoses. Methionine (Met) is believed to be one of the most readily oxidisable amino acid residues of protein. Bovine beta-lactogl

Periodate influencing diperiodatocuprate(III) oxidation of sulfur containing amino acid in aqueous alkaline medium

The diperiodatocuprate(III) (DPC) oxidation of DL-methionine, a sulfur containing amino acid, was studied spectrophotometrically in alkaline solution. The reaction rate was first order in the concentration of DPC and fractional order in the concentration

Kinetics and mechanism of oxidation of DL-methionine by hexacyanoferrate(III) in aqueous alkaline medium

The title reaction was studied spectrophotometrically. The reaction was found to be first order in [HCF] and fractional order each in [dl-methionine] and [OH-]. Initially added products did not alter the rate of reaction. The variation of ionic

Characterization by mass spectrometry and IRMPD spectroscopy of the sulfoxide group in oxidized methionine and related compounds

Methionine protein residues are prone to oxidation. To unravel the controversy about the mechanism of its one-electron oxidation, we characterised the main biological product, methionine sulfoxide, using mass spectrometry and IR multiple photon dissociation spectroscopy. Gas phase IR spectra in the 800-2000 cm-1 range of protonated methionine and its sulfoxide were recorded and compared to those computed for the lowest energy structures. The signature of the SO bond was clearly identified at around 1000 cm-1. Oxidation of methionine-lysine dipeptide by OH radicals in the presence of catalase revealed the formation of methionine sulfoxide upon one-electron oxidation.

Kinetic and mechanistic study of oxidation of L-methionine by Waugh-type enneamolybdomanganate(IV) in perchloric acid

The reaction between methionine and enneamolybdomanganate(IV) in perchloric acid was carried out under pseudo-first-order conditions keeping large excess of methionine. The orders in oxidant and substrate were found to be unity and 0.91, respectively. The reaction proceeds with rapid formation of complex between the reactants followed by its decomposition in a rate determining step. The accelerating effect of hydrogen ions on the reaction is due to the formation of active hexaprotonated oxidant species. The product of the reaction was found to be methionine sulfoxide. The reaction involves direct two-electron transfer step without any free radical intervention. The effect of ionic strength, solvent polarity and the activation parameters were also in support of the mechanism proposed.