N-Acetyl-L-cysteine ethyl ester Chemical Properties

Melting point:

44.1-44.5 °C

Boiling point:

337.6±32.0 °C(Predicted)

Density 

1.138±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMF: 30 mg/ml,DMSO: 30 mg/ml,PBS (pH 7.2): 10 mg/ml

form 

A crystalline solid

pka

9.17±0.10(Predicted)

color 

White to off-white

InChI

InChI=1S/C7H13NO3S/c1-3-11-7(10)6(4-12)8-5(2)9/h6,12H,3-4H2,1-2H3,(H,8,9)/t6-/m0/s1

InChIKey

MSMRAGNKRYVTCX-LURJTMIESA-N

SMILES

C(OCC)(=O)[C@H](CS)NC(C)=O

N-Acetyl-L-cysteine ethyl ester Usage And Synthesis

Description

N-acetyl-L-Cysteine ethyl ester is an esterified form of N-acetyl-L-cysteine (NAC; ). It has enhanced cell permeability in isolated perfused rat liver compared to NAC. N-acetyl-L-Cysteine ethyl ester (1 mM) prevents tert-butyl hydroperoxide-induced formation of methemoglobin in isolated human red blood cells. It increases glutathione levels in rat liver, kidney, heart, testis, and brain when administered at a dose of 50 mg/kg twice per day for two weeks. N-acetyl-L-Cysteine ethyl ester reduces increases in plasma aspartate aminotransferase (AST), alanine aminotransferase (ALT), and lactate dehydrogenase (LDH) levels induced by paracetamol (acetaminophen; ) in rats.

Uses

N-Acetyl-L-cysteine ethyl ester is an esterified form of N-acetyl-L-cysteine (NAC). N-Acetyl-L-cysteine ethyl ester exhibits enhanced cell permeability, and produce NAC and cysteine. N-Acetyl-L-cysteine ethyl ester increases circulating hydrogen sulfide (H2S) and can be used as an H2S producer. N-Acetyl-L-cysteine ethyl ester has the potential to substitute NAC as a mucolytic agent, and as a GSH-related antioxidant[1].

References

[1] Daniela Giustarini, et al. N-Acetylcysteine ethyl ester (NACET): a novel lipophilic cell-permeable cysteine derivative with an unusual pharmacokinetic feature and remarkable antioxidant potential. Biochem Pharmacol. 2012 Dec 1;84(11):1522-33. DOI:10.1016/j.bcp.2012.09.010

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