13100-69-1

Basic information

• Product Name: (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept- 1-yl)-2,4,6,8-nonatetraenoic acid
• Synonyms: (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept- 1-yl)-2,4,6,8-nonatetraenoic acid;5,6-epoxyretinoic acid;(2E,4E,6E,8E)-3,7-Dimethyl-9-[(2,6,6-trimethyl-1,2-epoxycyclohexan)-1-yl]-2,4,6,8-nonatetraenoic acid;5,6-Epoxy-5,6-dihydroretinoic acid;all-trans 5,6-Epoxy Retinoic Acid
• CAS NO: 13100-69-1
• Molecular Formula: C20H28O3
• Molecular Weight: 316.43
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Retinoids;Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals, Retinoids
• Mol File: 13100-69-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 160-162°C
• Boiling Point: 455.3°C at 760 mmHg
• Flash Point: 155.1°C
• Appearance: /
• Density: 1.101g/cm³
• Vapor Pressure: 1.48E-09mmHg at 25°C
• Refractive Index: 1.578
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Methanol (Very Slightly)
• Stability: Light Sensitive, Temperature Sensitive
• CAS DataBase Reference: (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept- 1-yl)-2,4,6,8-nonatetraenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept- 1-yl)-2,4,6,8-nonatetraenoic acid(13100-69-1)
• EPA Substance Registry System: (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept- 1-yl)-2,4,6,8-nonatetraenoic acid(13100-69-1)

Safety Data

• Hazardous Substances Data: 13100-69-1(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Solid

Uses

A metabolite of all-trans Retinoic acid (R250200).

InChI:InChI=1/C20H28O3/c1-15(8-6-9-16(2)14-17(21)22)10-13-20-18(3,4)11-7-12-19(20,5)23-20/h6,8-10,13-14H,7,11-12H2,1-5H3,(H,21,22)/b9-6+,13-10+,15-8+,16-14+

Upstream product

• 302-79-4 all-trans-retinoic-acid 
• 339-16-2 all-trans-methyl retinoate 
• 7432-30-6 Methyl ester of 5,6-epoxy-(E)-retinoic acid 
• 739-13-9 5,6-epoxy-5,6-dihydroretinal 

Downstream Products

• 3012-76-8 trans-5,8-epoxy-5,8-dihydroretinoic acid 
• 3012-76-8 cis-5,8-epoxy-5,8-dihydroretinoic acid 
• 7432-30-6 Methyl ester of 5,6-epoxy-(E)-retinoic acid 

Relevant articles and documents

Retinoic acid oxidation at high oxygen pressures: Evidence for spin-forbidden direct addition of triplet molecular oxygen

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Superoxidation of retinoic acid

Atmospheric pressure chemical ionization mass spectroscopy (APCI-MS) was used to examine the light-induced oxidation products of retinoic acid under conditions that favor and preclude its aggregation. We observed that in conditions that favor aggregation, i.e. in aqueous solutions, retinoic acid undergoes superoxidation to yield highly oxidized species. Oxidation is limited, however, in the absence of such communication, i.e. when the polyene is fully solvated. From a comparison of the measured MS with that obtained from chemical oxidation of retinoic acid under conditions that promote radical oxidation and singlet oxygen-mediated oxidation, we conclude that superoxidation is mediated by reactive oxygen species other than singlet oxygen.

Characterization of autoxidation products of retinoic acid

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