48042-96-2

Basic information

• Product Name: (S)-2-hydroxy-4-(methylthio)butyric acid
• Synonyms: (S)-2-hydroxy-4-(methylthio)butyric acid;(2S)-2-Hydroxy-4-(methylthio)butanoic acid;(2S)-2-Hydroxy-4-(methylthio)butyric acid;(S)-2-Hydroxy-4-(methylthio)butanoic acid;L-2-Hydroxy-4-(methylthio)butanoic acid;L-Methionine, hydroxy analog
• CAS NO: 48042-96-2
• Molecular Formula: C₅H₁₀O₃S
• Molecular Weight: 150.1961
• EINECS: 256-345-4
• Mol File: 48042-96-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 316.5°Cat760mmHg
• Flash Point: 145.2°C
• Appearance: /
• Density: 1.277g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.529
• CAS DataBase Reference: (S)-2-hydroxy-4-(methylthio)butyric acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-hydroxy-4-(methylthio)butyric acid(48042-96-2)
• EPA Substance Registry System: (S)-2-hydroxy-4-(methylthio)butyric acid(48042-96-2)

Safety Data

• Hazardous Substances Data: 48042-96-2(Hazardous Substances Data)

Usage

Uses

(2S)-2-Hydroxy-4-(methylthio)butanoic Acid is a Methionine Hydroxy analogue.

InChI:InChI=1/C5H10O3S/c1-9-3-2-4(6)5(7)8/h4,6H,2-3H2,1H3,(H,7,8)/t4-/m0/s1

Upstream product

• 63-68-3 L-methionine 
• 7664-93-9 sulfuric acid 
• 2488-15-5 N-tert-butoxycarbonyl-L-methionine 
• 49540-17-2 D,L-2-hydroxy-4-(methylthio)butanoic acid ethyl ester 

Relevant articles and documents

Facile synthesis of α-hydroxy carboxylic acids from the corresponding α-amino acids

An effective and improved procedure is developed for the synthesis of α-hydroxy carboxylic acids by treatment of the corresponding protonated α-amino acid with tert-butyl nitrite in 1,4-dioxane-water. The amino moiety must be protonated and located α to a carboxylic acid function in order to undergo initial diazotization and successive hydroxylation, since neither β-amino acids nor acid derivatives such as esters and amides undergo hydroxylations. The method is successfully applied for the synthesis of 18 proteinogenic amino acids.

Biocontrolled formal inversion or retention of L -α-amino acids to enantiopure (R)- or (S)-hydroxyacids

Natural L-α-amino acids and L-norleucine were transformed to the corresponding α-hydroxy acids by formal biocatalytic inversion or retention of absolute configuration. The one-pot transformation was achieved by a concurrent oxidation reduction cascade in aqueous media. A representative panel of enantiopure (R)- and (S)-2-hydroxy acids possessing aliphatic, aromatic and heteroaromatic moieties were isolated in high yield (67-85 %) and enantiopure form (>99 % ee) without requiring chromatographic purification.

Novel camphane-based anti-tuberculosis agents with nanomolar activity

A series of new amidoalcohols and amidodiols were designed on the base of the camphor scaffold and evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv and MDR strain 43. Some of the new compounds show 25 times higher activity than the classical anti-TB drug ethambutol. Small structural changes in the side chain shift the activity from micromolar to nanomolar inhibitory concentrations. Quantitative structure-activity relationship (QSAR) model is derived to guide the further lead optimization. Two hydrogen bond donors and up to three rings in the molecules are optimal for nanomolar activity. The camphane-based amides present novel promising scaffolds for antimycobacterial agents.