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

Description

N-acetyl-S-allylcysteine, also known as N-Acetyl-S-allyl-L-cysteine, is a principal metabolite of L-deoxyalliin, a water-soluble organosulfur compound derived from garlic. It possesses neuroprotective and antioxidative activities and is readily detected in plasma and urine. The conversion of L-deoxyalliin to N-acetyl-S-allylcysteine is mediated by a family of flavin-containing monooxygenases. It is a white solid.

Uses

Used in Pharmaceutical Industry:
N-acetyl-S-allylcysteine is used as a pharmaceutical compound for its neuroprotective and antioxidative properties. It is particularly beneficial in the development of treatments for various neurological disorders and conditions related to oxidative stress.
Used in Nutraceutical Industry:
N-acetyl-S-allylcysteine is used as a nutraceutical ingredient for its health-promoting and disease-preventing properties. It can be incorporated into dietary supplements and functional foods to support overall health and well-being.
Used in Cosmetic Industry:
N-acetyl-S-allylcysteine is used as an active ingredient in the cosmetic industry for its antioxidant and skin-protective properties. It can be included in skincare products to help protect the skin from environmental stressors and promote a healthy, youthful appearance.
Used in Research Applications:
N-acetyl-S-allylcysteine is used as a research compound for studying the biological effects of organosulfur compounds derived from garlic. It can be utilized in laboratory experiments to investigate its potential therapeutic applications and mechanisms of action.

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

Downstream Products

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

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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