129119-13-7

Basic information

• Product Name: N-benzyloxycarbonyl-S-<<5,8a-dimethyl-3a,5,6,7,8,8a,9,9a-octahydro-2(3H)-oxo-3-naphtho<2,3-b>furanyl>methyl>-L-cysteinyl-L-alanine methyl ester
• Synonyms: N-benzyloxycarbonyl-S-<<5,8a-dimethyl-3a,5,6,7,8,8a,9,9a-octahydro-2(3H)-oxo-3-naphtho<2,3-b>furanyl>methyl>-L-cysteinyl-L-alanine methyl ester
• CAS NO: 129119-13-7
• Molecular Weight: 572.723
• Mol File: 129119-13-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-benzyloxycarbonyl-S-<<5,8a-dimethyl-3a,5,6,7,8,8a,9,9a-octahydro-2(3H)-oxo-3-naphtho<2,3-b>furanyl>methyl>-L-cysteinyl-L-alanine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyloxycarbonyl-S-<<5,8a-dimethyl-3a,5,6,7,8,8a,9,9a-octahydro-2(3H)-oxo-3-naphtho<2,3-b>furanyl>methyl>-L-cysteinyl-L-alanine methyl ester(129119-13-7)
• EPA Substance Registry System: N-benzyloxycarbonyl-S-<<5,8a-dimethyl-3a,5,6,7,8,8a,9,9a-octahydro-2(3H)-oxo-3-naphtho<2,3-b>furanyl>methyl>-L-cysteinyl-L-alanine methyl ester(129119-13-7)

Safety Data

• Hazardous Substances Data: 129119-13-7(Hazardous Substances Data)

Upstream product

• 129119-12-6 N-carbobenzoxy-L-cysteinylglycyl-L-alanine methyl ester 
• 546-43-0 alantolactone 
• 129119-11-5 N-benzyloxycarbonyl-S-trityl-L-cysteinyl-L-alanine benzyl ester 
• 26311-04-6 N-benzyloxycarbonyl-S-trityl-L-cysteine 

Relevant articles and documents

Suppression of the skin response to alantolactone in alantolactone-sensitized guinea pigs treated with N-acetyl-L-cysteinyl-L-alanine methyl ester

Induction of a state of tolerance (hyposensitization) in alantolactone-sensitized guinea pigs was attempted by subcutaneous injections of S-(dihydroalantolacton-10-yl)-L-cysteinyl-L-alanine methyl ester 7, N-acetyl-L-cysteinyl-L-alanine methyl ester 11 or N-acetyl-L-cysteine. Compound 7 was prepared by addition of N-benzyloxycarbonyl-L-cysteinyl-L-alanine methyl ester 5 to alantolactone, followed by the removal of the Z-group. Dipeptide 11 was obtained from N-acetyl-S-ethylcarbamoyl-L-cysteinyl-L-alanine methyl ester. Treatment of dipeptide 5 with HBr-AcOH mixture afforded mainly the S-acetyl derivative 10, from which dipeptide 11 was also obtained. Biological assays showed that the alantolactone-adduct 7 or N-acetyl-L-cysteine did not significantly modify the positive skin response to alantolactone in alantolactone-sensitive guinea pigs. In marked contrast, dipeptide 11 significantly decreased the skin reaction to alantolactone tested at either 0.25 or 0.08 μg. Control animals did not show skin responses to alantolactone neither after treatment with dipeptides 7, 11 or N-acetyl-L-cysteine. The data suggest that dipeptide 11 is an efficient and non-toxic tolerogen in the case of guinea pigs sensitized to alantolactone.