59587-09-6

Basic information

• Product Name: N-Acetyl-L-cysteine ethyl ester
• Synonyms: N-Acetyl-L-cysteine ethyl ester;L-Cysteine, N-acetyl-, ethyl ester;N-Acetylcysteine ethylester;(R)-ethyl 2-acetaMido-3-Mercaptopropanoate;(R)-Methyl 2-acetaMido-3-Mercaptopropanoate;-Ethyl 2-acetamido-3-mercaptopropanoate
• CAS NO: 59587-09-6
• Molecular Formula: C₇H₁₃NO₃S
• Molecular Weight: 191.25
• Mol File: 59587-09-6.mol
• Article Data: 15

Chemical Properties

• Melting Point: 44.1-44.5 °C
• Boiling Point: 337.6 °C at 760 mmHg
• Flash Point: 158 °C
• Appearance: /
• Density: 1.138 g/cm³
• Vapor Pressure: 0.000104mmHg at 25°C
• Refractive Index: 1.48
• Storage Temp.: 2-8°C
• PKA: 9.17±0.10(Predicted)
• CAS DataBase Reference: N-Acetyl-L-cysteine ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetyl-L-cysteine ethyl ester(59587-09-6)
• EPA Substance Registry System: N-Acetyl-L-cysteine ethyl ester(59587-09-6)

Safety Data

• Hazardous Substances Data: 59587-09-6(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/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

Synthetic route

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

Conditions	Yield
With Hexanethiol; C28H41NOP2Ru; hydrogen In 1,4-dioxane at 150℃; under 15001.5 Torr; for 36h; Autoclave; chemoselective reaction;	A 98% B 80 %Spectr.

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

Conditions	Yield
With thionyl chloride at 0 - 20℃; for 4h; Inert atmosphere;	47%
With thionyl chloride at 20℃; for 3.5h;	47%
With thionyl chloride at 30℃; for 3h; Esterification;	46%

(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)

Conditions	Yield
In dimethyl sulfoxide at 25℃; for 7.5h; other solvents;	43%

N,N'-diacetyl-L-cystine diethyl ester (24037-21-6) → (R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6)

Conditions	Yield
With hydrogenchloride; zinc

N-Boc-L-cysteine ethyl ester (118143-52-5) → (R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2.)I2 2: 43 percent / dimethylsulfoxide / 7.5 h / 25 °C / other solvents View Scheme

N-acetyl-S-trityl-L-cysteine (27486-87-9) → (R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 20 °C 2: trifluoroacetic acid; triethylsilane / dichloromethane / 0 - 20 °C View Scheme

C26H27NO3S (1032314-56-9) → (R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6)

Conditions	Yield
With triethylsilane; trifluoroacetic acid In dichloromethane at 0 - 20℃;

N-acetylcystein (616-91-1) → (R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 20 °C 3: trifluoroacetic acid; triethylsilane / dichloromethane / 0 - 20 °C View Scheme

L-cystein ethyl ester (3411-58-3) + acetic anhydride (108-24-7) → (R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6)

Conditions	Yield
In dichloromethane Inert atmosphere;

(R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6) + O-acetylsyringic acid chloride (39657-47-1) → (R)-ethyl-2-amino-3-(4-acetoxy-3,5-dimethoxybenzoylthio)propanoate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 5 - 20℃; for 3h;	87%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 5 - 20℃; for 3h;	87%

(R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6) + 4,4′-(cyclopent-1-ene-1,2-diyl)bis(5-methylthiophene-2-carboxylic acid) (331432-79-2) → (2R,2'R)-diethyl 3,3'-((4,4'-(cyclopent-1-ene-1,2-diyl)bis(5-methylthiophene-2,2'-carbonyl))-bis(sulfanediyl))bis(2-acetamidopropanoate) (1613317-63-7)

Conditions	Yield
Stage #1: 4,4′-(cyclopent-1-ene-1,2-diyl)bis(5-methylthiophene-2-carboxylic acid) With dmap; triethylamine; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: (R)-2-acetylamino-3-mercapto-propionic acid ethyl ester In N,N-dimethyl-formamide at 20℃; for 16h;	86%

(R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6) + O-acetylsyringic acid chloride (39657-47-1) → C18H23NO8S

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 4h;	85%

(R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6) + (1,3-dibenzyl-4,5-diphenylimidazol-2-ylidene)gold(I) chloride → (1,3-dibenzyl-4,5-diphenylimidazol-2-ylidene)gold(I)-N-acetyl-L-cysteine ethyl Ester

Conditions	Yield
With potassium carbonate In water; ethyl acetate at 20℃; for 24h;	78%

(R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6) + sodium 2-propenylthiosulfate (6363-01-5) → N-acetyl-S-allylsulfanyl-L-cysteine ethyl ester

Conditions	Yield
With triethylamine In methanol at 20℃; for 3h;	77%

(R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6) + β-D-glucose pentaacetate (604-69-3) → N-acetyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-cysteine ethyl ester (270062-01-6)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 3h; Etherification;	45%

(R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6) + methyl 6-(((S,E)-5-((E)-oct-2-en-1-ylidene)-4-oxocyclopent-2-en-1-yl)amino)-6-oxohexanoate → methyl 6-(((1R,5R,E)-5-(((R)-2-acetamido-3-ethoxy-3-oxopropyl)thio)-2-((E)-oct-2-en-1-ylidene)-3-oxocyclopentyl)amino)-6-oxohexanoate

Conditions	Yield
With triethylamine In dimethyl sulfoxide	29%

(R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6) → N-acetyl-3-(β-D-glucopyranosyl)-cysteine ethyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 45 percent / BF3*Et2O / CH2Cl2 / 3 h / 20 °C 2: 60 percent / Et3N / methanol / 16 h View Scheme

(R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6) → (R)-2-(acetylamino)-3-mercaptopropanamide (38520-57-9)

Conditions	Yield
With ammonia In ethanol

(R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6) + pivaloyl chloride (3282-30-2) → S-pivaloyl-N-acetyl-L-cysteine ethyl ester + S-pivaloyl-N-acetyl-acetyl-L-cysteine ethyl ester

Conditions	Yield
With pyridine; hydrogenchloride In chloroform; water

(R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6) + propionyl chloride (79-03-8) → S-propionyl-N-acetyl-L-cysteine ethyl ester

Conditions	Yield
With pyridine; hydrogenchloride In chloroform; di-isopropyl ether; water
With pyridine; hydrogenchloride In chloroform; di-isopropyl ether; water

(R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6) + isobutyryl chloride (79-30-1) → S-isobutyryl-N-acetyl-L-cysteine ethyl ester

Conditions	Yield
With pyridine; hydrogenchloride In chloroform; di-isopropyl ether; water
With pyridine; hydrogenchloride In chloroform; di-isopropyl ether; water

(R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6) + pivaloyl chloride (3282-30-2) → S-pivaloyl-N-acetyl-L-cysteine ethyl ester

Conditions	Yield
With pyridine; hydrogenchloride In chloroform; water

(R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6) + 1-(1-hydroperoxy-1-methylethyl)cyclohexene (42953-13-9) → C16H27NO4S (1039118-73-4) + (1R,2R)-2-(1'-hydroxy-1'-methyl-ethyl)-1-cyclohexanol (1040363-82-3)

Conditions	Yield
With iron(III) chloride In water; acetonitrile at 20℃; for 1.5h; Title compound not separated from byproducts.;

(R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6) → S-nitroso-N-acetylcysteine ethyl ester

Conditions	Yield
With disodium hydrogenphosphate; phosphoric acid; tetrasodium ethylenediamine-N,N,N',N'-tetraacetate; sodium nitrite In water at 22℃; pH=7.4; Cooling with liquid nitrogen;

(R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6) + (4R,5aS,7aS,7bR)-5,5a,6,7,7a,7b-hexahydro-7b-hydroxy-4-methyl-indeno[1,7-bc]furan-2(4H)-one (133613-71-5) → 3β-(N-acetyl L-cysteine ethyl ester)-2αβ,3-dihydrogaliellalactone

Conditions	Yield
With triethylamine In methanol at 20℃; for 24h;	22 mg

1-hydroxyprop-2-ynehexacarbonyldicobalt (12264-12-9) + (R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6) → C16H15Co2NO9S

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 0℃; Nicholas Reaction; Inert atmosphere; Glovebox; Schlenk technique;	70 mg

(R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6) + methyl (E)-4-chloro-4-oxo-2-butenoate (17081-97-9) → methyl (E)-3-[(2R)-2-acetylamino-2-ethoxycarbonylethylthiocarbonyl]acrylate

Conditions	Yield
In diethyl ether at 20℃;

(R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6) + methyl (E)-4-chloro-4-oxo-2-butenoate (17081-97-9) → methyl (E)-4-{(1R)-1-ethoxycarbonyl-2-[(methylthio)carbonyl]ethylamino}-4-oxo-2-butenoate

Conditions	Yield
In dichloromethane at -78 - 20℃; Inert atmosphere;

(R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6) + N-((5-(dimethylamino)naphthalen-1-yl)sulfonyl)acrylamide (127488-68-0) → C22H29N3O6S2

Conditions	Yield
With triethylamine

(R)-2-acetylamino-3-mercapto-propionic acid ethyl ester (59587-09-6) + ethyl 2-diazo-2-(4-methoxyphenyl) acetate (107445-17-0) → ethyl N-acetyl-S-(2-ethoxy-1-(4-methoxyphenyl)-2-oxoeth-yl)-L-cysteinate + ethyl N-acetyl-S-(2-ethoxy-1-(4-methoxyphenyl)-2-oxoeth-yl)-L-cysteinate

Conditions	Yield
In dichloromethane at 20℃; for 12h; Schlenk technique; Inert atmosphere; Irradiation; Overall yield = 92 percent; Overall yield = 176.8 mg; Optical yield = 9.091 percent de;

Upstream product

• 64-17-5 ethanol 
• 616-91-1 N-acetylcystein 
• 3411-58-3 L-cystein ethyl ester 
• 108-24-7 acetic anhydride 
• 1032314-56-9 C₂₆H₂₇NO₃S 
• 27486-87-9 N-acetyl-S-trityl-L-cysteine 
• 118143-52-5 N-Boc-L-cysteine ethyl ester 
• 84310-90-7 (R)-2-Amino-3-(1,5-diacetoxy-3-methoxy-2-methyl-9-oxo-9H-xanthen-4-yldisulfanyl)-propionic acid ethyl ester 
• 24037-21-6 N,N'-diacetyl-L-cystine diethyl ester 

Downstream Products

• 1039118-73-4 C₁₆H₂₇NO₄S 
• 1040363-82-3 (1R,2R)-2-(1'-hydroxy-1'-methyl-ethyl)-1-cyclohexanol 

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