84489-15-6

Basic information

• Product Name: (2R)-2-acetamido-3-[2-(4-chlorophenoxy)-2-methyl-propanoyl]sulfanyl-pr opanoic acid
• Synonyms: (2R)-2-acetamido-3-[2-(4-chlorophenoxy)-2-methyl-propanoyl]sulfanyl-pr opanoic acid;clofibrate mercapturate
• CAS NO: 84489-15-6
• Molecular Formula: C15H18ClNO5S
• Molecular Weight: 359.8251
• Mol File: 84489-15-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 580°Cat760mmHg
• Flash Point: 304.5°C
• Appearance: /
• Density: 1.335g/cm³
• Vapor Pressure: 2.72E-14mmHg at 25°C
• Refractive Index: 1.566
• CAS DataBase Reference: (2R)-2-acetamido-3-[2-(4-chlorophenoxy)-2-methyl-propanoyl]sulfanyl-pr opanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2-acetamido-3-[2-(4-chlorophenoxy)-2-methyl-propanoyl]sulfanyl-pr opanoic acid(84489-15-6)
• EPA Substance Registry System: (2R)-2-acetamido-3-[2-(4-chlorophenoxy)-2-methyl-propanoyl]sulfanyl-pr opanoic acid(84489-15-6)

Safety Data

• Hazardous Substances Data: 84489-15-6(Hazardous Substances Data)

Usage

General Description

(2R)-2-acetamido-3-[2-(4-chlorophenoxy)-2-methyl-propanoyl]sulfanyl-propanoic acid is a chemical compound that consists of a sulfanyl group attached to a propanoic acid backbone, with an acetamido group and a 4-chlorophenoxy-2-methyl-propanoyl group attached to the sulfur atom. (2R)-2-acetamido-3-[2-(4-chlorophenoxy)-2-methyl-propanoyl]sulfanyl-pr opanoic acid is a type of thiol derivative, which is a class of organic compounds containing a sulfur-hydrogen bond. Thiol derivatives play important roles in various biochemical processes, including the synthesis of proteins and the regulation of enzyme activity. The specific chemical structure of (2R)-2-acetamido-3-[2-(4-chlorophenoxy)-2-methyl-propanoyl]sulfanyl-propanoic acid suggests that it may have potential applications in pharmaceuticals or as a research tool in biochemistry. Further investigation is needed to fully understand the properties and potential uses of this chemical compound.

InChI:InChI=1/C15H18ClNO5S/c1-9(18)17-12(13(19)20)8-23-14(21)15(2,3)22-11-6-4-10(16)5-7-11/h4-7,12H,8H2,1-3H3,(H,17,18)(H,19,20)/t12-/m0/s1

Upstream product

• 616-91-1 N-acetylcystein 

Relevant articles and documents

Interaction of γ-glutamyltranspeptidase with clofibryl-S-acyl-glutathione in vitro and in vivo in rat

Clofibric acid (CA) is metabolized to chemically reactive acylating products that can transacylate glutathione to form clofibryl-S-acyl-glutathione (CA-SG) in vitro and in vivo. We investigated the first step in the degradation of CA-SG to the mercapturic acid conjugate, clofibryl-S-acyl-N-acetylcysteine (CA-SNAC), which is catalyzed by γ-glutamyltranspeptidase (γ-GT). After γ-GT mediated cleavage of glutamate from CA-SG, the product clofibryl-S-acylcysteinylglycine (CA-S-CG) should undergo an intramolecular rearrangement reaction [Tate, S. S. (1975) FEBS Lett. 54, 319-322] to form clofibryl-N-acyl-cysteinylglycine (CA-N-CG). We performed in vitro studies incubating CA-SG with γ-GT to determine the products formed, and in vivo studies examining the products excreted in urine after dosing rats with CA-SG or CA. Thus, CA-SG (0.1 mM) was incubated with γ-GT (0.1 unit/mL) in buffer (pH 7.4, 25 °C) and analyzed for products formed by reversed-phase HPLC and electrospray mass spectrometry (ESI/MS). Results showed that CA-SG is degraded completely after 6 h of incubation leading to the formation of two products, CA-N-CG and its disulfide, with no detection of CA-S-CG thioester. After 36 h of incubation, only the disulfide remained in the incubation. Treatment of the disulfide with dithiothreitol led to the reappearance of CA-N-CG. ESI/LC/MS analysis of urine (16 h) extracts of CA-SG-dosed rats (200 mg/kg, iv) showed that CA-SG is degraded to CA-N-CG, CA-N-acyl-cysteine (CA-N-C) and their respective S-methylated products. The mercapturic acid conjugate (CA-SNAC) was found as a minor product. dAnalysis of urine extracts from CA-dosed rats (200 mg/kg, ip) resulted in the detection of clofibryl-N-acyl-cysteine (CAN-C), but no evidence for the formation of CA-SNAC was obtained. These in vitro and in vivo experiments indicate that γ-GT mediated degradation of clofibryl-S-acyl-glutathione leads primarily to the formation and excretion of clofibryl-N-acyl-cysteine products rather than the S-acyl-NAC conjugate.