N-Acetyl-L-cysteine ethyl ester

Base Information

• Chemical Name: N-Acetyl-L-cysteine ethyl ester
• CAS No.: 59587-09-6
• Molecular Formula: C7H13NO3S
• Molecular Weight: 191.251
• Mol file: 59587-09-6.mol

Synonyms:N-Acetyl-L-cysteineethyl ester;N-Acetylcysteine ethyl ester;L-Cysteine, N-acetyl-, ethyl ester;N-Acetylcysteine ethylester;

Chemical Property of N-Acetyl-L-cysteine ethyl ester

Chemical Property:

• Vapor Pressure: 0.000104mmHg at 25°C
• Melting Point: 44.1-44.5 °C
• Refractive Index: 1.48
• Boiling Point: 337.6 °C at 760 mmHg
• PKA: 9.17±0.10(Predicted)
• Flash Point: 158 °C
• PSA: 97.69000
• Density: 1.138 g/cm³
• LogP: 0.82430
• Storage Temp.: 2-8°C

Purity/Quality:

98%, ^*data from raw suppliers

(R)-Ethyl2-acetamido-3-mercaptopropanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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.

Technology Process of N-Acetyl-L-cysteine ethyl ester

There total 10 articles about N-Acetyl-L-cysteine ethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

S,N-diacetyl-L-cysteine monoethyl ester → (R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6) + ethanol (64-17-5)

Guidance literature:

With Hexanethiol; C₂₈H₄₁NOP₂Ru; hydrogen; In 1,4-dioxane; at 150 ℃; for 36h; under 15001.5 Torr; chemoselective reaction; Autoclave;

DOI:10.1021/jacs.0c10884

Reference yield: 47.0%

ethanol (64-17-5) + N-acetylcystein (616-91-1,7696-05-1) → (R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6)

Guidance literature:

With thionyl chloride; at 0 - 20 ℃; for 4h; Inert atmosphere;

Reference yield: 43.0%

(R)-2-Amino-3-(1,5-diacetoxy-3-methoxy-2-methyl-9-oxo-9H-xanthen-4-yldisulfanyl)-propionic acid ethyl ester (84310-90-7) → (R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6)

Guidance literature:

In dimethyl sulfoxide; at 25 ℃; for 7.5h; other solvents;

DOI:10.1016/0040-4039(81)80049-4

upstream raw materials:

N,N'-diacetyl-L-cystine diethyl ester

(R)-2-Amino-3-(1,5-diacetoxy-3-methoxy-2-methyl-9-oxo-9H-xanthen-4-yldisulfanyl)-propionic acid ethyl ester

ethanol

N-acetylcystein

Downstream raw materials:

C₁₆H₂₇NO₄S

(1R,2R)-2-(1'-hydroxy-1'-methyl-ethyl)-1-cyclohexanol

Refernces

• 1、 Tosi, Gian Marco,Giustarini, Daniela,Franci, Lorenzo,Minetti, Alberto,Imperatore, Francesco,Caldi, Elena,Fiorenzani, Paolo,Aloisi, Anna Maria,Sparatore, Anna,Rossi, Ranieri,Chiariello, Mario,Orlandini, Maurizio,Galvagni, Federico. "Superior properties of N-acetylcysteine ethyl ester over n-acetyl cysteine to prevent retinal pigment epithelial cells oxidative damage". . p. 1 - 12. Retrieved 2021.
• 2、 Conway, Lorna,Riccio, Anna,Santoro, M. Gabriella,Evans, Paul. "Synthesis of the 4-aza cyclopentenone analogue of Δ12,14-15-deoxy-PGJ2 and S-cysteine adducts". supporting information. . Retrieved 2020/05/18.