18725-37-6

Basic information

• Product Name: dacisteine
• Synonyms: dacisteine;N,S-Diacetyl-L-cysteine;N-Acetyl-L-cysteine acetate;N-Acetyl-S-(methylcarbonyl)-L-cysteine;S,N-Diacetyl-L-cysteine;N,S-Diacetyl-;Acetylcysteine EP IMpurity D;(R)-2-Acetamido-3-(acetylthio)propanoic acid
• CAS NO: 18725-37-6
• Molecular Formula: C₇H₁₁NO₄S
• Molecular Weight: 205.23
• EINECS: 242-537-5
• Product Categories: Amino Acids & Derivatives;Sulfur & Selenium Compounds
• Mol File: 18725-37-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 114-116°C
• Boiling Point: 446.8°C at 760 mmHg
• Flash Point: 224°C
• Appearance: /
• Density: 1.314g/cm³
• Vapor Pressure: 3.13E-09mmHg at 25°C
• Refractive Index: 1.522
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.15±0.10(Predicted)
• CAS DataBase Reference: dacisteine(CAS DataBase Reference)
• NIST Chemistry Reference: dacisteine(18725-37-6)
• EPA Substance Registry System: dacisteine(18725-37-6)

Safety Data

• Hazardous Substances Data: 18725-37-6(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 18725-37-6 differently. You can refer to the following data:
1. N,S-Diacetyl-L-cysteine (Acetylcysteine EP Impurity D) is a double-prodrugs of L-cysteine: differential protection against acetaminophen-induced hepatotoxicity in mice (1,2,3).
2. A double-prodrugs of L-cysteine

InChI:InChI=1/C7H11NO4S/c1-4(9)8-6(7(11)12)3-13-5(2)10/h6H,3H2,1-2H3,(H,8,9)(H,11,12)/t6-/m0/s1

Upstream product

• 19538-81-9 N,S-diacetyl-cysteine 
• 52-90-4 L-Cysteine 
• 108-24-7 acetic anhydride 
• 52-89-1 l-cysteine hydrochloride 
• 616-91-1 N-acetylcystein 
• 546-88-3 acetylhydroxamic acid 

Downstream Products

• 668481-15-0 Acetic acid (1S,2R,3R,4S,5S,6R)-2,3,4,5-tetraacetoxy-6-[(2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-((R)-2-acetylamino-3-acetylsulfanyl-propionylamino)-tetrahydro-pyran-2-yloxy]-cyclohexyl ester 
• 669091-43-4 1-D-myo-inosityl-2-(N-acetyl-L-cysteinyl)amino-2-deoxy-α-D-glucopyranoside disulfide 
• 158761-05-8 1-D-myo-inosityl-2-deoxy-2-(N-acetamido-L-cysteinamido)-α-D-glucopyranoside 
• 192126-76-4 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol 
• 1078-38-2 N-acetyl-N'-isonicotinoylhydrazine 
• 35143-96-5 N,S-Diacetyl-L-cystein-p-acetoxyanilid 
• 35143-95-4 N-Acetyl-L-cystein-p-hydroxyanilid 
• 36914-44-0 N,S-Diacetylcysteinamid 
• 62147-02-8 N_.S-Diacetyl-DL-cystein-p-nitrophenylester 
• 35143-94-3 N,S-Diacetyl-L-Cystein-p-hydroxy-anilid 

Relevant articles and documents

Direct Observation of Acyl Nitroso Compounds in Aqueous Solution and the Kinetics of Their Reactions with Amines, Thiols, and Hydroxamic Acids

Acyl nitroso compounds or nitrosocarhonyls (RC(O)N=O) are reactive short-lived electrophiles, and their hydrolysis and reactions with nucleophiles produce HNO. Previously, direct detection of acyl nitroso species in nonaqueous media has been provided by time-resolved infrared spectroscopy demonstrating that its half-life is about 1 ms. In the present study hydroxamic acids (RC(O)NHOH) are oxidized electrochemically in buffered aqueous solutions (pH 5.9-10.2) yielding transient species characterized by their maximal absorption at 314-330 nm. These transient species decompose via a first-order reaction yielding mainly HNO and the respective carboxylic acid and therefore are ascribed to RC(O)N=O. The sufficiently long half-life of RC(O)N=O in aqueous solution allows for the first time the study of the kinetics of its reactions with various nucleophiles demonstrating that the nucleophilic reactivity follows the order thiolate > hydroxamate > amine. Metal chelates of CH3C(O)NHOH catalyze the hydrolysis of CH3C(O)N=O at the efficacy order of CuII > ZnII > NiII > CoII where only CuII catalyzes the hydrolysis also in the absence of the hydroxamate. Finally, oxidation of hydroxamic acids generates HNO, and the rate of this process is determined by the half-life of the respective acyl nitroso compound.

First Total Synthesis of Mycothiol and Mycothiol Disulfide

(Matrix presented) The first total synthesis of mycothiol and mycothiol disulfide was achieved by linking D-2,3,4,5,6-penta-O-acetyl-myo-inositol, O-(3,4,6-tri-O-acetyl)-2-azido-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate, and N,S-diacetyl-L-cysteine and deprotecting peracetylated mycothiol. The first full spectral characterization is reported for underivatized mycothiol. The structure of mycothiol was confirmed by spectral analysis of the known bimane derivative.

Analysis of acetylcysteine by capillary electrophoresis (CE). Part 2: Determination of side components

The purity of N-acetyl-L-cysteine was tested by capillary electrophoresis (CE). The efficiency was optimized up to a theoretical plate number N of several hundred thousand. The most important impurities, N,N-diacetylcystine and cystine were detectable in amounts below 0.05%. These and other possible by-products were synthesized and their identity was confirmed by NMR spectroscopy. All these compounds could be separated.