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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

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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Journal of the Chemical Society. Perkin Transactions 1, 2345-2345 (1988)
Ewa Maria Musiol-Kroll et al.
Antibiotics (Basel, Switzerland), 7(3) (2018-07-20)
Polyketides belong to the most valuable natural products, including diverse bioactive compounds, such as antibiotics, anticancer drugs, antifungal agents, immunosuppressants and others. Their structures are assembled by polyketide synthases (PKSs). Modular PKSs are composed of modules, which involve sets of
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)
Micah J Bodner et al.
Organic letters, 11(16), 3606-3609 (2009-07-21)
Efficient syntheses of N-acetyl thienamycin and epithienamycin A in their readily deprotected form are reported where three contiguous stereocenters are established in a single catalytic asymmetric azetidinone-forming reaction. These examples are a template for synthesizing C-5/C-6 cis or trans carbapenems
N Singh et al.
Biochemical and biophysical research communications, 131(2), 786-792 (1985-09-16)
The acetyl transacylase activity of the fatty acid synthase from yeast has been investigated using p-nitrophenylthiol acetate. The chromophoric nature of the nitrophenylthiol moiety affords a convenient spectrophotometric assay for the transacylase function as well as a means to investigate
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