50409-83-1

Basic information

• Product Name: S-mandelylglutathione
• Synonyms: S-mandelylglutathione;N-[N-(L-γ-Glutamyl)-S-mandeloyl-L-cysteinyl]glycine
• CAS NO: 50409-83-1
• Molecular Formula: C₁₈H₂₃N₃O₈S
• Molecular Weight: 441.46
• Mol File: 50409-83-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 859.9°C at 760 mmHg
• Flash Point: 473.8°C
• Appearance: /
• Density: 1.46g/cm³
• Vapor Pressure: 1.63E-31mmHg at 25°C
• Refractive Index: 1.615
• CAS DataBase Reference: S-mandelylglutathione(CAS DataBase Reference)
• NIST Chemistry Reference: S-mandelylglutathione(50409-83-1)
• EPA Substance Registry System: S-mandelylglutathione(50409-83-1)

Safety Data

• Hazardous Substances Data: 50409-83-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H23N3O8S/c19-11(17(27)28)6-7-13(22)21-12(16(26)20-8-14(23)24)9-30-18(29)15(25)10-4-2-1-3-5-10/h1-5,11-12,15,25H,6-9,19H2,(H,20,26)(H,21,22)(H,23,24)(H,27,28)/t11-,12-,15?/m0/s1

Upstream product

• 70-18-8 GLUTATHIONE 
• 1074-12-0 phenylglyoxal hydrate 
• 67972-70-7 (S)-2-Amino-4-[(R)-1-(carboxymethyl-carbamoyl)-2-(1-hydroxy-2-oxo-2-phenyl-ethylsulfanyl)-ethylcarbamoyl]-butyric acid 

Downstream Products

• 90-64-2 d-(-)-mandelic acid 

Relevant articles and documents

S-2-Hydroxyacylglutathione-Derivatives: Enzymatic Preparation, Purification and Characterisation

S-2-Hydroxyacylglutathione derivatives have been prepared by enzymatic synthesis from α-oxoaldehydes and reduced glutathione in the presence of glyoxalase I.S-D-Lactoylglutathione, S-D-mandelylglutathione, S-glycolylglutathione and S-L-glyceroylglutathione were prepared from methylglyoxal, phenylglyoxal, glyoxal and hydroxypyruvaldehyde, respectively.They were purified by ion exchange chromatography on Dowex 1 on a gram scale.Analytical data and re-evaluated extinction coefficients for these compounds are presented.The method described provides a reliable, large-scale procedure for the preparation and purification of S-acylglutathiones of increasing biological and pharmacological interest.

Reactions of Thiols with Phenylglyoxal to Give Thiomandelic S-Esters Formation of Hemithioacetals and Their Rearrangement

Equilibrium constants Kh for the addition of 2-mercaptoethanol and glutathione to phenylglyoxal to form hemithioacetals were determined spectrophotometrically over the pH range 7-10.The observed Kh values decrease sigmoidally with pH as the thiol ionizes.Rearrangement of hemithioacetals formed from phenylglyoxal and various thiols was kinetically investigated.The rates increase with thiol concentration following a saturation curve to give Kh identical with the spectrophotometric value.The rearrangement is subject to general base catalysis.The solvent isotope effect on the rate of the rearrangement, kH2O/kd2O, is nearly 1.0; that on the equilibrium, KH2Oh/KD2Oh, is 0.38.The results strongly support the mechanism involving proton transfers through an enediol intermediate.