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363340

Sigma-Aldrich

N-Acetylcysteamine

95%

Synonym(s):

N-(2-Mercaptoethyl)acetamide

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About This Item

Linear Formula:
CH3CONHCH2CH2SH
CAS Number:
1190-73-4
Molecular Weight:
119.19
MDL number:
MFCD00037831
UNSPSC Code:
12352100
eCl@ss:
32160406
PubChem Substance ID:
24862192
NACRES:
NA.22

Quality Level

200

Assay

95%

form

liquid

refractive index

n20/D 1.511 (lit.)

bp

138-140 °C/7 mmHg (lit.)

mp

6-7 °C (lit.)

density

1.121 g/mL at 25 °C (lit.)

SMILES string

CC(=O)NCCS

InChI

1S/C4H9NOS/c1-4(6)5-2-3-7/h7H,2-3H2,1H3,(H,5,6)

InChI key

AXFZADXWLMXITO-UHFFFAOYSA-N

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General description

N-Acetylcysteamine, also known as N-(2-Mercaptoethyl) acetamide, is a derivative of cysteamine, that is commonly used as a building block for the synthesis of alkylated thiol and thioesters via esterification.

Application

N-Acetylcysteamine can be used as a building block to synthesize:
  • N







  • -acetylcysteamine (SNAC) thioesters by reacting with various acid derivatives in the presence of 1,1′-carbonyldiimidazole (CDI).      
  • Thieno[2,3-c]pyrrole derivatives via three-component reaction of 2-acetyl-3-thiophenecarboxaldehyde and various amines.
  •  Carbapenems, a class of beta-lactam antibiotic agents.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Magoichi Sako et al.
The Journal of organic chemistry, 63(20), 6947-6951 (2001-10-24)
4H-[1,2,5]Oxadiazolo[3,4-d]pyrimidine-5,7-dione 1-oxides (2) are conveniently prepared in high yields by the oxidative intramolecular cyclization of 6-amino-5-nitro-1H-pyrimidine-2,4-diones (1) employing iodosylbenzene diacetate as an oxidant in the presence of lithium hydride. The generation of nitric oxide (NO) and NO-related species from 2
Isolation, properties, and regulation of a mitochondrial acyl coenzyme A thioesterase from pig heart.
K Y Lee et al.
The Journal of biological chemistry, 254(11), 4516-4523 (1979-06-10)
Cell cycle arrest and apoptosis induction by an anticancer chalcone epoxide
Haiyong H, et al
Archives of Pharmacal Research, 343, 429-439 (2010)
Cynthia M Hong et al.
Organic & biomolecular chemistry, 11(18), 2932-2935 (2013-03-29)
A three-component reaction has been developed that allows the regioselective synthesis of thieno[2,3-c]pyrroles. The reaction is based on the ability of 2-acetyl-3-thiophenecarboxaldehyde to react with amine and thiol nucleophiles to produce the corresponding tri-substituted thieno[2,3-c]pyrroles, with water as the only
S A Moore et al.
The Journal of biological chemistry, 257(18), 10874-10881 (1982-09-25)
Succinyl phosphate reacts rapidly with the thiol N-acetyl-beta-mercaptoethylamine (a CoA analog) to form the succinate thiol ester. This is a chemical model for the enzymic reaction of CoA transferase. It is demonstrated that: 1) the chemical reaction is stepwise, proceeding
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