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Merck
CN

138061

N-Acetyl-L-cysteine

98%

Synonym(s):

LNAC, NAC

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About This Item

Linear Formula:
HSCH2CH(NHCOCH3)CO2H
CAS Number:
Molecular Weight:
163.19
Beilstein:
1724426
EC Number:
MDL number:
UNSPSC Code:
12352209
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Assay

98%

optical activity

[α]25/D +4.5°, c = 2 in H2O

mp

106-108 °C (lit.)

SMILES string

CC(=O)N[C@@H](CS)C(O)=O

InChI

1S/C5H9NO3S/c1-3(7)6-4(2-10)5(8)9/h4,10H,2H2,1H3,(H,6,7)(H,8,9)/t4-/m0/s1

InChI key

PWKSKIMOESPYIA-BYPYZUCNSA-N

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Application

Useful reagent in a variety of biochemical applications, such as the derivatization of anticancer triazenes and the synthesis of matlystatin A via 1,4-Michael addition.

Biochem/physiol Actions

Antioxidant and mucolytic agent. Increases cellular pools of free radical scavengers. Reported to prevent apoptosis in neuronal cells but induce apoptosis in smooth muscle cells. Inhibits HIV replication. May serve as a substrate for microsomal glutathione transferase.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Journal of the Chemical Society. Perkin Transactions 1, 3241-3241 (1991)
Tetrahedron Letters, 34, 8477-8477 (1993)
Kristell Le Gal et al.
Science translational medicine, 7(308), 308re8-308re8 (2015-10-09)
Antioxidants in the diet and supplements are widely used to protect against cancer, but clinical trials with antioxidants do not support this concept. Some trials show that antioxidants actually increase cancer risk and a study in mice showed that antioxidants
Marialucia Gallorini et al.
Biomaterials, 56, 114-128 (2015-05-03)
Oxidative stress due to increased formation of reactive oxygen species (ROS) in target cells of dental resin monomers like 2-hydroxyethyl methacrylate (HEMA) is a major mechanism underlying the disturbance of vital cell functions including mineralization and differentiation, responses of the
Francielli Licks et al.
World journal of gastroenterology, 21(43), 12351-12360 (2015-11-26)
To evaluate the antioxidant effect of N-acetylcysteine (NAC) on the stomach of rats with portal hypertension. Twenty-four male Wistar rats weighing ± 250 g were divided into four experimental groups (n = 6 each): Sham-operated (SO), SO + NAC, partial

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