23127-41-5

Basic information

• Product Name: N-acetyl-S-allylcysteine
• Synonyms: N-acetyl-S-allylcysteine;N-Acetyl-S-allyl-L-cysteine;AllylMercapturic Acid;L-N-Acetyl-3-(allylthio)alanine;N-Acetyl-S-2-propen-1-yl-L-cysteine;S-AllylMercapturic Acid
• CAS NO: 23127-41-5
• Molecular Formula: C₈H₁₃NO₃S
• Molecular Weight: 203.26
• Product Categories: Amino Acids & Derivatives;Sulfur & Selenium Compounds
• Mol File: 23127-41-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 444 °C at 760 mmHg
• Flash Point: 222.3 °C
• Appearance: /
• Density: 1.191 g/cm³
• Vapor Pressure: 4.01E-09mmHg at 25°C
• Refractive Index: 1.521
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: N-acetyl-S-allylcysteine(CAS DataBase Reference)
• NIST Chemistry Reference: N-acetyl-S-allylcysteine(23127-41-5)
• EPA Substance Registry System: N-acetyl-S-allylcysteine(23127-41-5)

Safety Data

• Hazardous Substances Data: 23127-41-5(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

L-Deoxyalliin , also known as S-allyl-L-cysteine, is a water soluble organosulfur compound derived from garlic that has neuroprotective and antioxidative activities. N-Acetyl-S-allyl-L-cysteine is a principal metabolite of L-deoxyalliin in humans, mice, rats, and dogs. It is readily detected in plasma and urine. The conversion of L-deoxyalliin to N-acetyl-S-allyl-L-cysteine appears to be mediated by a family of flavin-containing monooxygenases.

InChI:InChI=1/C8H13NO3S/c1-3-4-13-5-7(8(11)12)9-6(2)10/h3,7H,1,4-5H2,2H3,(H,9,10)(H,11,12)

Upstream product

• 21593-77-1 S-allyl cysteine 
• 108-24-7 acetic anhydride 
• 49621-03-6 S-propenyl-L-cysteine 
• 616-91-1 N-acetylcystein 
• 556-27-4 S-allyl-L-cysteine sulfoxide 
• 106-95-6 allyl bromide 
• 507-09-5 thioacetic acid 
• 64-19-7 acetic acid 

Downstream Products

• 870-23-5 prop-2-ene-1-thiol 
• 7664-41-7 ammonia 
• 64-19-7 acetic acid 
• 127-17-3 2-oxo-propionic acid 
• 21593-77-1 S-allyl cysteine 

Relevant articles and documents

H2S-Donating Doxorubicins May Overcome Cardiotoxicity and Multidrug Resistance

Doxorubicin (DOXO) is one of the most effective antineoplastic agents in clinical practice. Its use is limited by acute and chronic side effects, in particular by its cardiotoxicity and by the rapid development of resistance to it. As part of a program ai

Development of a class-selective enzyme-linked immunosorbent assay for mercapturic acids in human urine

Epidemiological and toxicological studies often require the analysis of large numbers of samples for biological markers of exposure. The goal of this work was to develop a class-selective ELISA to detect groups of structurally closely related mercapturic acids with small nonpolar S-substituents. An assay was developed with strong recognition for mercapturates including S-benzylmercapturic acid (IC50 = 0.018 μmol/L), S-n-hexylmercapturic acid (IC50 = 0.021 μmol/L), S-phenylmercapturic acid (IC50 = 0.024 μmol/L), and S-cyclohexylmethylmercapturic acid (IC50 = 0.042 μmol/L). The same assay also showed weaker recognition for S-(1-hydroxynaphthal-2-yl)mercapturic acid and S-allylmercapturic acid (IC50 = 1.1 and 1.7 μmol/L, respectively). Subtle modifications to the hapten linker structure of the coating antigen proved to have a strong impact on the selectivity and the specificity of the assay. A slightly modified assay showed high recognition for S-benzylmercapturic acid (IC50 = 0.018 μmol/L) and weaker recognition for seven other mercapturic acids (IC50 = 0.021-10 μmol/L). Strong positive assay responses were detected in 12 urine samples obtained from persons with no known occupational exposure to exogenous electrophilic xenobiotics. Solid phase extraction and cross-reactivity indicated that the presumptive immunoreactive materials were similar in size and polarity to S-benzylmercapturic acid. The assay was more selective to mercapturic acids than the spectrophotometric thioether assay.

The synthesis of mercapturic acids and their esters

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