38030-59-0

Basic information

• Product Name: 4-Hydroxyretinoic acid methyl ester
• Synonyms: 4-Hydroxyretinoic acid methyl ester
• CAS NO: 38030-59-0
• Molecular Weight: 330.467
• Mol File: 38030-59-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 4-Hydroxyretinoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxyretinoic acid methyl ester(38030-59-0)
• EPA Substance Registry System: 4-Hydroxyretinoic acid methyl ester(38030-59-0)

Safety Data

• Hazardous Substances Data: 38030-59-0(Hazardous Substances Data)

Upstream product

• 132333-25-6 methyl 4-bromoretinoate 
• 339-16-2 all-trans-methyl retinoate 
• 302-79-4 all-trans-retinoic-acid 
• 71748-57-7 4-Oxo-retinoic acid methyl ester 
• 186581-53-3 diazomethane 
• 66592-72-1 4-hydroxyretinoic acid 
• 67-56-1 methanol 
• 81121-19-9 (2E,4E,6E,8E)-9-(3-Acetoxy-2,6,6-trimethyl-cyclohex-1-enyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid ethyl ester 

Downstream Products

• 71748-57-7 4-Oxo-retinoic acid methyl ester 
• 303731-03-5 (±)-4-(4H-1,2,4-triazol-4-yl) methyl retinoate 
• 303731-02-4 (±)-4-(1H-1,2,4-triazol-1-yl) methyl retinoate 
• 163808-81-9 (13E)-3,7-dimethyl-9-[(3RS)-3-methoxy-2,6,6-trimethylcyclohexenyl]-2,4,6,8-nontetraenoate methyl ester 
• 38030-57-8 4-ketoretinoic acid 
• 303731-01-3 4-(1H-imidazole-1-yl)retinoic acid 
• 303731-00-2 (±)-4-(1H-imidazol-1-yl)-methyl retinoate 

Relevant articles and documents

Free Radical Oxidation of (E)-Retinoic Acid by Prostaglandin H Synthase

Cooxidative metabolism of all-trans (E)-retinoic acid (RA) by prostaglandin H synthase was investigated employing ram seminal vesicle microsomes (RSVM) or purified, RSVM-derived enzyme. RA was shown to undergo hydroperoxide [H2O2 or 5-phenyl-4-penten-1-yl hydroperoxide (PPHP)]- or arachidonic acid-dependent cooxidation by microsomal prostaglandin H (PGH) synthase as evidenced by UV spectroscopic analysis of reaction mixtures. Cooxidation of RA by microsomal or purified PGH synthase, using PPHP as substrate, was characterized by uptake of dioxygen which was first order with respect to enzyme concentration. Dioxygen uptake was inhibited by the peroxidase reducing substrate 2-methoxyphenol. In addition, O2 uptake was inhibited by the spin trap nitrobenzene. ESR spin trapping studies, using α-phenyl-N-tert-butylnitrone (PBN) as the spin trap, demonstrated the formation of RAP-PBN adducts, characterized by hyperfine coupling constants of aH = 3.2 G and aN = 15.8 G. Reverse phase HPLC analysis of reaction mixtures demonstrated the formation of 4-hydroxy-RA, 5,6-epoxy-RA, 4-oxo-RA, (13Z)-retinoic acid, and other geometric isomers which were identified on the basis of cochromatography with synthetic standards, UV spectroscopy, and/or mass spectrometry. Mechanisms are proposed for the hydroperoxide-dependent, PGH synthase-catalyzed oxidation of RA that are consistent with these results.

4-OXO-FENRETINIDE, ADMINISTERED ALONE AND IN COMBINATION WITH FENRETINIDE, AS PREVENTIVE AND THERAPEUTIC AGENT FOR CANCER

A drug based on a metabolite of fenretinide, or N-(4-hydroxyphenyl)retinamide (4-HPR), specifically 4-oxo-N-(4-hydroxyphenyl)retinamide (4-oxo-4-HPR), is used in the treatment of different kinds of tumors, in particular in the treatment of ovarian carcino

Potent inhibition of retinoic acid metabolism enzyme(s) by novel azolyl retinoids

Novel (±)-4-azolyl retinoic acid analogues 4, 5, 7 and 8 have been designed and synthesized and have been shown to be powerful inhibitors of hamster microsomal all-trans-retinoic acid 4-hydroxylase enzyme(s). (±)-4-(1H-Imidazol-1-yl)retinoic acid (4) is t