7432-30-6

Basic information

• Product Name: 5,6-Epoxy-5,6-dihydroretinoic acid methyl ester
• Synonyms: 5,6-Epoxy-5,6-dihydroretinoic acid methyl ester
• CAS NO: 7432-30-6
• Molecular Formula: C21H30O3
• Molecular Weight: 330.4611
• Mol File: 7432-30-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 419.3°Cat760mmHg
• Flash Point: 178.2°C
• Appearance: /
• Density: 1.057g/cm³
• Vapor Pressure: 3.08E-07mmHg at 25°C
• Refractive Index: 1.554
• CAS DataBase Reference: 5,6-Epoxy-5,6-dihydroretinoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-Epoxy-5,6-dihydroretinoic acid methyl ester(7432-30-6)
• EPA Substance Registry System: 5,6-Epoxy-5,6-dihydroretinoic acid methyl ester(7432-30-6)

Safety Data

• Hazardous Substances Data: 7432-30-6(Hazardous Substances Data)

Usage

Uses

Methyl 5,6-Monoepoxyretinoate is an impurity in the synthesis of Ro 22-5112 (R637180), a retinoid that has been used in a QSAR analysis for the use of retinoids as a carcinogenesis inhibitor.

InChI:InChI=1/C21H30O3/c1-16(9-7-10-17(2)15-18(22)23-6)11-14-21-19(3,4)12-8-13-20(21,5)24-21/h7,9-11,14-15H,8,12-13H2,1-6H3/b10-7+,14-11+,16-9-,17-15-

Upstream product

• 339-16-2 all-trans-methyl retinoate 
• 186581-53-3 diazomethane 
• 302-79-4 all-trans-retinoic-acid 
• 13100-69-1 all-trans-5,6-Epoxyretinoic acid 
• 67-56-1 methanol 
• 739-13-9 5,6-epoxy-5,6-dihydroretinal 

Downstream Products

• 13100-69-1 all-trans-5,6-Epoxyretinoic acid 

Relevant articles and documents

Retinoic acid-dependent stimulation of 2,2'-azobis(2-amidinopropane)- initiated autoxidation of linoleic acid in sodium dodecyl sulfate micelles: A novel prooxidant effect of retinoic acid

(E)-Retinoic acid (RA) was shown to stimulate the rate of 2,2'-azobis(2- amidinopropane) (AAPH)-initiated autoxidation of linoleic acid (18:2) in sodium dodecyl sulfate (SDS) micelles. RA-dependent stimulation of 18:2 autoxidation was characterized by enhanced rates of dioxygen uptake which were linear with retinoid concentration. In contrast, 5,6-epoxy-RA, a major oxidation product of RA, failed to affect the rate of dioxygen consumption at all concentrations tested. RA was also shown to stimulate peroxyl radical- dependent oxidation of styrene to the corresponding oxirane when styrene was included in the micellar system as a molecular probe. Furthermore, unequivocal evidence of RA-dependent stimulation of 18:2 autoxidation was obtained by relative quantitation of 13-hydroxy-(9Z, 11E)-octadecadienoic acid (13-HODE) plus 9-hydroxy-(10E,12Z)-octadecadienoic acid (9-HODE) production. In addition, enhanced carboncentered radical formation was demonstrated in the presence of RA by EPR spectroscopy using α-(4-pyridyl 1- oxide)-N-tert-butylnitrone (4-POBN) as a spin trap. Analysis and quantitation of RA oxidation products indicated that RA was oxidized to one primary product, 5,6-epoxy-RA, which was identified on the basis of cochromatography with synthetic standard (in a reverse-phase HPLC system), electronic absorption spectroscopy, and positive chemical ionization mass spectrometry of the corresponding methyl ester. Other minor oxidation products were also detected but not characterized. In contrast, reaction mixtures devoid of 18:2 failed to demonstrate significant retinoid oxidation. Mechanisms are proposed to account for the prooxidant effects of RA in this system.

5,6-epoxidation of all-trans-retinoic acid with soybean lipoxygenase-2 and -3

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