389135-53-9

Basic information

• Product Name: L-Cysteine, S-(2,5-dihydroxyphenyl)-, ethyl ester, hydrochloride
• CAS NO: 389135-53-9
• Molecular Formula: C11H15NO4S.ClH
• Molecular Weight: 293.771
• Mol File: 389135-53-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: L-Cysteine, S-(2,5-dihydroxyphenyl)-, ethyl ester, hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: L-Cysteine, S-(2,5-dihydroxyphenyl)-, ethyl ester, hydrochloride(389135-53-9)
• EPA Substance Registry System: L-Cysteine, S-(2,5-dihydroxyphenyl)-, ethyl ester, hydrochloride(389135-53-9)

Safety Data

• Hazardous Substances Data: 389135-53-9(Hazardous Substances Data)

Upstream product

• 868-59-7 L-cysteine ethyl ester hydrochloride 
• 106-51-4 p-benzoquinone 

Downstream Products

• 59587-30-3 6-hydroxy-benzothiazole-2-carboxylic acid ethyl 
• 389135-55-1 Ethyl 2-ethoxy-7-hydroxy-2H-benzo[1,4]thiazine-3-carboxylate 

Relevant articles and documents

A new synthesis of 2-cyano-6-hydroxybenzothiazole, the key intermediate of d-luciferin, starting from 1,4-benzoquinone

2-Cyano-6-hydroxybenzothiazole is the key intermediate for the synthesis of d-luciferin, the natural substrate of firefly luciferases. A new synthesis of 2-cyano-6-hydroxybenzothiazole has been realized starting from the reaction of 1,4-benzoquinone with l-cysteine ethyl ester, followed by oxidation-cyclization of the intermediate ethyl (R)-2-amino-3-(2,5-dihydroxyphenylsulfanyl)propan-oate hydrochloride to 2-carbethoxy-6-hydroxybenzothiazole. A suitable protection of this intermediate and a conversion to the corresponding nitrile gave, after deprotection, 2-cyano-6-hydroxybenzothiazole (32% yield from 1,4-benzoquinone). This nitrile reacts with d-cysteine to afford d-luciferin at room temperature in nearly quantitative yield (90-95%).