16729-22-9

Basic information

• Product Name: (3E,5E,7E)-9-[(3E)-2,4,4-Trimethyl-1-cyclohexen-3-ylidene]-3,7-dimethylnona-3,5,7-trien-1-ol
• Synonyms: (3E,5E,7E)-9-[(3E)-2,4,4-Trimethyl-1-cyclohexen-3-ylidene]-3,7-dimethylnona-3,5,7-trien-1-ol;all-trans-retro-Vitamin A;all-trans-Retro Retinol;Vitamin A Impurity C
• CAS NO: 16729-22-9
• Molecular Formula: C₂₀H₃₀O
• Molecular Weight: 286.45
• Product Categories: Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Retinoids
• Mol File: 16729-22-9.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3E,5E,7E)-9-[(3E)-2,4,4-Trimethyl-1-cyclohexen-3-ylidene]-3,7-dimethylnona-3,5,7-trien-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3E,5E,7E)-9-[(3E)-2,4,4-Trimethyl-1-cyclohexen-3-ylidene]-3,7-dimethylnona-3,5,7-trien-1-ol(16729-22-9)
• EPA Substance Registry System: (3E,5E,7E)-9-[(3E)-2,4,4-Trimethyl-1-cyclohexen-3-ylidene]-3,7-dimethylnona-3,5,7-trien-1-ol(16729-22-9)

Safety Data

• Hazardous Substances Data: 16729-22-9(Hazardous Substances Data)

Usage

Uses

A degradation product of Vitamin A (R252000). Vitamin A impurity.

Production Methods

Retro-vitamin A is obtained by treatment of retinol in the presence of concentrated hydrobromic acid. In the case of retinoic acid and retinal, reisomerization is possible after conversion to appropriate derivatives such as the acid chloride or the hydroquinone adduct.

Upstream product

• 127-47-9 Retinol acetate 
• 68-26-8 RETINOL 
• 7631-44-9 (6E,8E,10E,12E)-retroretinyl acetate 

Relevant articles and documents

Iron(III)Porphinate/H2O2-Mediated Conversion of All-(E)-Retinol

The reaction of hydrogen peroxide with all-(E)-retinol (1) catalyzed by (meso-tetraphenylporphinato)iron(III) led to the formation of 4-hydroxyretinol (2), 4-oxoretinol (3), 5,8-epoxyretinol (4), 5,6-epoxyretinol (5), 3-dehydroretinol (6), all-(E)- and 12-(Z)-retroretinol (7/7a) as well as all-(E)- and 12-(Z)-anhydroretinol (8/8a) as major non-volatile products.The conversion products were characterized by comparison of their chromatographic (HPLC) and spectroscopic data (UV; MS; 1H and 13C NMR) with those of synthesized reference compounds.The observed product formation supports the hypothesis of a C4 centered radical as the key intermediate of all-(E)-retinol conversion. - Keywords: 5,6- and 5,8-Epoxyretinol, 4-Hydroxyretinol, 4-Oxoretinol, Retinol Conversion