219965-90-9

Basic information

• Product Name: S-(2,3,4-Trihydroxybutyl)mercapturic Acid
• Synonyms: N-Acetyl-S-(2,3,4-trihydroxybutyl)-L-cysteine;S-(2,3,4-Trihydroxybutyl)mercapturic Acid;S-(2,3,4-Trihydroxybutyl)mercapturic Acid (Mixture of Diatstereomers);N-Acetyl-S-(2,3,4-trihydroxybutyl)-
• CAS NO: 219965-90-9
• Molecular Formula: C9H17NO6S
• Molecular Weight: 267.3
• Product Categories: Various Metabolites and Impurities;Metabolites & Impurities;Mutagenesis Research Chemicals
• Mol File: 219965-90-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 689.927°C at 760 mmHg
• Flash Point: 371.055°C
• Appearance: /
• Density: 1.443g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.577
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.30±0.10(Predicted)
• CAS DataBase Reference: S-(2,3,4-Trihydroxybutyl)mercapturic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: S-(2,3,4-Trihydroxybutyl)mercapturic Acid(219965-90-9)
• EPA Substance Registry System: S-(2,3,4-Trihydroxybutyl)mercapturic Acid(219965-90-9)

Safety Data

• Hazardous Substances Data: 219965-90-9(Hazardous Substances Data)

Usage

Description

S-(2,3,4-Trihydroxybutyl)mercapturic Acid is a metabolite of butadiene and butadiene monoepoxide, which is a colorless oil. It is relevant to cancer susceptibility due to its chemical properties and interactions with biological systems.

Uses

Used in Pharmaceutical Industry:
S-(2,3,4-Trihydroxybutyl)mercapturic Acid is used as a biomarker for assessing exposure to butadiene and butadiene monoepoxide, which are known carcinogens. Its detection in biological samples can help in understanding the relationship between exposure to these chemicals and cancer susceptibility.
Used in Environmental Monitoring:
S-(2,3,4-Trihydroxybutyl)mercapturic Acid is used as an indicator of environmental contamination by butadiene and butadiene monoepoxide. Monitoring its presence in air, water, and soil samples can provide valuable information on the extent of pollution and potential health risks associated with these chemicals.
Used in Toxicology Research:
S-(2,3,4-Trihydroxybutyl)mercapturic Acid is used as a research tool in toxicology studies to investigate the mechanisms of action and potential health effects of butadiene and butadiene monoepoxide exposure. This can contribute to the development of strategies for risk assessment, prevention, and mitigation of exposure-related health issues.

InChI:InChI=1/C9H17NO6S/c1-5(12)10-6(9(15)16)3-17-4-8(14)7(13)2-11/h6-8,11,13-14H,2-4H2,1H3,(H,10,12)(H,15,16)/t6-,7?,8?/m0/s1

Upstream product

• 17177-50-3 (+/-)-(1,2-Dihydroxyethyl)oxirane 
• 616-91-1 N-acetylcystein 

Relevant articles and documents

Identification of novel metabolites of butadiene monoepoxide in rats and mice

Differences in the metabolism of 1,3-butadiene (Bd) in rats and mice may account for the observed species difference in carcinogenicity. Previous studies of the metabolic fate of Bd have identified epoxide formation as a key metabolic transformation which gives 1,2-epoxy-3-butene (BMO), although some evidence of aldehyde metabolites is reported. In this study, male Sprague-Dawley rats and male B6C3F1 mice received single doses of [4- 14C]BMO at 1, 5, 20, and 50 mg/kg of body weight (0.014, 0.071, 0.286, and 0.714 mmol/kg of body weight). Analysis of urinary metabolites indicated that both species preferentially metabolize BMO by direct reaction with GSH when given by ip administration. The excretion of (R)-2-(N-acetyl-L-cystein-S- yl)-1-hydroxybut-3-ene (IIa), 1-(N-acetyl-L-cystein-S-yl)-2-(S)-hydroxybut- 3-ene (IIb), 1-(N-acetyl-L-cystein-S-yl)-2-(R)-hydroxybut-3-ene (IIc), and (S)-2-(N-acetyl-L-cystein-S-yl)-1-hydroxybut-3-ene (IId) accounted for 48- 64% of urinary radioactivity in rats and 46-54% in mice. The metabolites originating from the R-stereoisomer of BMO (IIc and IId) predominated over those arising from the S-stereoisomer (IIa and IIb) in both species. IIc was formed preferentially in mice and IId in rats. The corresponding mercaptoacetic acids, S-(1-hydroxybut-3-en-2-yl)mercaptoacetic acid (IIf) and S-(2-hydroxybut-3-en-1-yl)mercaptoacetic acid (IIg), were identified only in mouse urine (ca. 20% of the recovered radioactivity). 4-(N-Acetyl-L-cystein- S-yl)-1,2-dihydroxybutane (Ia), a metabolite derived from hydrolysis of BMO, accounted for 10-17% of the radioactivity in rat and 6-10% in mouse urine. 4- (N-Acetyl-L-cystein-S-yl)-2-hydroxybutanoic acid (Ib), 3-(N-acetyl-L-cystein- S-yl)propan-1-ol (Ic), and 3-(N-acetyl-L-cystein-S-yl)propanoic acid (Id), also derived from the hydrolysis of BMO, were only present in the rat. Metabolites of 1,2,3,4-diepoxybutane (DEB) were not detected after administration of BMO in rat or mouse urine. This study showed both quantitative and qualitative differences in the metabolism of BMO with varying doses and between species. The data aid in the safety evaluation of Bd and contribute to the interpretation of mathematical models developed for quantitative risk assessment and extrapolation of animals to humans.