Identification of a decarboxylation product of retinoic acid.
The oxidative decarboxylation of retinoic acid was investigated utilizing a model system consisting of all-trans-retinoic acid, H2O2 and horseradish peroxidase. The decarboxylation products were purified by high-performance liquid chromatography on bonded, octadecylsilane columns. Based on mass spectral, nuclear magnetic resonance, ultraviolet and Fourier transform infrared analyses, the major decarboxylation product was identified as a 4-oxo-C19 aldehyde with a hydroxyl group on the side chain at C9, specifically 8-(2,6,6-trimethyl-3-oxocyclohex-1-enyl)2,6-dimethyl-6-hydroxyoctatrienal.
D000447:Aldehydes / Q000032:analysis; D055598:Chemical Phenomena; D002621:Chemistry; D003653:Decarboxylation; D005583:Fourier Analysis; D006735:Horseradish Peroxidase; D006861:Hydrogen Peroxide; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D013729:Terpenes / Q000032:analysis; D014212:Tretinoin / Q000032:analysis*
D000447:Aldehydes; D013729:Terpenes; D014212:Tretinoin; D006861:Hydrogen Peroxide; D006735:Horseradish Peroxidase