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

Description

(2R)-2-acetamido-3-[2-(4-chlorophenoxy)-2-methyl-propanoyl]sulfanyl-propanoic acid is a complex organic thiol derivative featuring a propanoic acid backbone with a sulfanyl group, an acetamido group, and a 4-chlorophenoxy-2-methyl-propanoyl group attached to the sulfur atom. This unique structure positions it as a potential candidate for pharmaceutical applications or as a research tool in biochemistry, given the significant roles thiol derivatives play in biochemical processes such as protein synthesis and enzyme regulation.

Uses

Used in Pharmaceutical Industry:
(2R)-2-acetamido-3-[2-(4-chlorophenoxy)-2-methyl-propanoyl]sulfanyl-propanoic acid is used as a potential therapeutic agent for various conditions due to its unique chemical structure and the functional groups it contains, which may offer specific biological activities.
Used in Biochemical Research:
In the field of biochemistry, (2R)-2-acetamido-3-[2-(4-chlorophenoxy)-2-methyl-propanoyl]sulfanyl-propanoic acid serves as a valuable research tool, enabling scientists to study the roles of thiol derivatives in protein synthesis, enzyme regulation, and other biochemical processes.
Further investigation is necessary to fully understand the properties and potential uses of this chemical compound, as its specific applications and efficacy will depend on its interaction with biological systems and its stability under various conditions.

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.