39638-34-1

Basic information

• Product Name: (R)-2-hydroxy-4-(methylthio)butyric acid
• Synonyms: (R)-2-hydroxy-4-(methylthio)butyric acid;(2R)-2-Hydroxy-4-(methylthio)butanoic acid;D-2-Hydroxy-4-methylmercaptobutyric acid;L-Methionine-D-hydroxy analog
• CAS NO: 39638-34-1
• Molecular Formula: C₅H₁₀O₃S
• Molecular Weight: 150.1961
• EINECS: 254-555-0
• Mol File: 39638-34-1.mol
• Article Data: 4

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: (R)-2-hydroxy-4-(methylthio)butyric acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-hydroxy-4-(methylthio)butyric acid(39638-34-1)
• EPA Substance Registry System: (R)-2-hydroxy-4-(methylthio)butyric acid(39638-34-1)

Safety Data

• Hazardous Substances Data: 39638-34-1(Hazardous Substances Data)

Usage

General Description

(R)-2-hydroxy-4-(methylthio)butyric acid is a compound that consists of a butyric acid molecule with a hydroxy group and a methylthio group attached at specific positions. It is a chiral molecule, meaning it has a non-superimposable mirror image, and the (R)- prefix indicates the orientation of its chiral center. (R)-2-hydroxy-4-(methylthio)butyric acid is found in nature and is a precursor in the biosynthesis of methionine, an essential amino acid. It also serves as a precursor for the production of the sulfur-containing antioxidant glutathione. Additionally, (R)-2-hydroxy-4-(methylthio)butyric acid is used in the fermentation industry as a feed additive for livestock, where it can improve animal performance and health. Overall, this compound plays important roles in biological processes and has practical applications in agriculture.

InChI:InChI=1/C5H10O3S/c1-9-3-2-4(6)5(7)8/h4,6H,2-3H2,1H3,(H,7,8)/t4-/m1/s1

Upstream product

• 583-91-5 2-hydroxy 4-methylthiobutyric acid 
• 63-68-3 L-methionine 
• 108033-83-6 (R)-2-Hydroxy-4-methylsulfanyl-butyronitrile 

Relevant articles and documents

Light-Driven Kinetic Resolution of α-Functionalized Carboxylic Acids Enabled by an Engineered Fatty Acid Photodecarboxylase

Chiral α-functionalized carboxylic acids are valuable precursors for a variety of medicines and natural products. Herein, we described an engineered fatty acid photodecarboxylase (CvFAP)-catalyzed kinetic resolution of α-amino acids and α-hydroxy acids, which provides the unreacted R-configured substrates with high yields and excellent stereoselectivity (ee up to 99 %). This efficient light-driven process requires neither NADPH recycling nor prior preparation of esters, which were required in previous biocatalytic approaches. The structure-guided engineering strategy is based on the scanning of large amino acids at hotspots to narrow the substrate binding tunnel. To the best of our knowledge, this is the first example of asymmetric catalysis by an engineered CvFAP.

A Convenient Route to (R)-α-Hydroxy Carboxylic Acids and (2R)-1-Amino-2-alkanols from (R)-Cyanohydrins

(R)-Cyanohydrins, prepared in good to excellent yields with high optical purity by enzyme-catalyzed addition of hydrogen cyanide to aldehydes in organic solvents, are hydrolyzed with concentrated hydrochloric acid at ambient temperature, usually in very high yield, without any trace of racemization to give (R)-α-hydroxy carboxylic acids.Likewise, no racemization is observed by direct reduction of the (R)-cyanohydrins with lithium aluminium hydride to give (2R)-1-amino-2-alkanols.