19542-77-9

Basic information

• Product Name: N-ACETYL-S-BENZYL-L-CYSTEINE
• Synonyms: N-ACETYL-S-BENZYL-L-CYSTEINE;ACETYL BENZYL CYSTEINE;s-benzyl-n-acetyl-l-cysteine;Benzylmercapturic Acid;N-Acetyl-3-(benzylthio)-alanine;N-Acetyl-S-(phenylmethyl)-L-cysteine;(R)-2-(Acetylamino)-3-(benzylthio)propionic acid;(R)-3-(Benzylthio)-2-(acetylamino)propionic acid
• CAS NO: 19542-77-9
• Molecular Formula: C₁₂H₁₅NO₃S
• Molecular Weight: 253.32
• Product Categories: Amino Acids;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 19542-77-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 144-146°C
• Boiling Point: 506.2 °C at 760 mmHg
• Flash Point: 259.9 °C
• Appearance: White to yellow crystalline powder.
• Density: 1.2516 (rough estimate)
• Vapor Pressure: 4.55E-11mmHg at 25°C
• Refractive Index: 1.6280 (estimate)
• Storage Temp.: 0-6°C
• Solubility: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• PKA: 3.37±0.10(Predicted)
• CAS DataBase Reference: N-ACETYL-S-BENZYL-L-CYSTEINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-ACETYL-S-BENZYL-L-CYSTEINE(19542-77-9)
• EPA Substance Registry System: N-ACETYL-S-BENZYL-L-CYSTEINE(19542-77-9)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 19542-77-9(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

A metabolite of Toluene

InChI:InChI=1/C12H15NO3S/c1-9(14)13-11(12(15)16)8-17-7-10-5-3-2-4-6-10/h2-6,11H,7-8H2,1H3,(H,13,14)(H,15,16)/p-1/t11-/m0/s1

Upstream product

• 463-51-4 Ketene 
• 3054-01-1 S-benzyl-L-cysteine 
• 6803-17-4 γ-Glu-BzlCys-Gly 
• 108-24-7 acetic anhydride 
• 616-91-1 N-acetylcystein 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 5680-65-9 2-amino-3-(benzylthio)propionic acid 
• 3054-01-1 (D)-2-Amino-3-(benzylthio)propanoic acid 
• 90843-71-3 3-(benzylthio)pyruvic acid 
• 19519-04-1 N-methyl-S-benzyl-L-cysteine 

Downstream Products

• 72286-24-9 N-(N-acetyl-3-(Ξ)-phenylmethanesulfinyl-L-alanyl)-glycine ethyl ester 
• 72286-35-2 N-((5R)-7-methyl-2ξ-phenyl-4,5-dihydro-[1,3,6]oxathiazepine-5r-carbonyl)-glycine ethyl ester 
• 15353-95-4 Ac-L-Cys(Bzl)-NHMe 
• 72286-22-7 (R)-2-Acetylamino-3-phenylmethanesulfinyl-propionic acid 
• 72286-29-4 N-(N-acetyl-S-benzyl-L-cysteinyl)-glycine ethyl ester 
• 52808-14-7 Ac-L-Cys(Bzl)NEV 
• 3054-01-1 S-benzyl-L-cysteine 

Relevant articles and documents

Initial intraorgan formation of mercapturic acid

The disposition of S-benzyl-glutathione (BSG) in male Wistar rats was evaluated by the HPLC method to examine whether the kidney and liver contributed independently to the biosynthesis of S-benzyl-N-acetylcysteine (BNAc), a mercapturic acid (Chart 1). After intravenous injection, BSG was rapidly transported in both the kidney and the liver at a ratio of about 7:3. Simultaneously, a large amount of BNAc was found in both the kidney and the liver. In the kidney, S-benzyl-cysteine (BCys) reached a maximum concentration (Cmax) at 2 min after BSG injection, whereas BNAc reached Cmax within 3 to 5 min. The generation of BNAc was also observed in the liver. While renal BNAc reached Cmax within 3 to 5 min, hepatic BNAc reached Cmax around 5 min after BSG injection. Moreover, the elimination half-life of the BNAc after intravenous injection of the BSG was equivalent to that observed after intravenous injection of the BNAc itself. These results demonstrate that the kidney contributes to the initial intraorgan generation of BNAc and that this mercapturic acid is also synthesized in the liver and preferentially excreted into urine.

Cobalt assisted cleavage of S-S bonds and a base-free synthesis of mercapturic acids

Base free transformation of PhSSPh to sulfides, PhSR (R = alkyl, benzyl, allyl, acyl) and N-acetyl-L-cystine to mercapturic acids [AcNHCH(COOH)CH2SR, R = alkyl, benzyl, allyl, acyl] have been achieved using Zn/cat. CoCl2/organic halide in MeCN at room temperature.