15353-44-3

Basic information

• Product Name: all-trans-4-hydroxyretinol
• Synonyms: all-trans-4-hydroxyretinol
• CAS NO: 15353-44-3
• Molecular Weight: 302.457
• Mol File: 15353-44-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: all-trans-4-hydroxyretinol(CAS DataBase Reference)
• NIST Chemistry Reference: all-trans-4-hydroxyretinol(15353-44-3)
• EPA Substance Registry System: all-trans-4-hydroxyretinol(15353-44-3)

Safety Data

• Hazardous Substances Data: 15353-44-3(Hazardous Substances Data)

Upstream product

• 68-26-8 RETINOL 
• 1026935-65-8 (2E,4E)-3-Methyl-5-(2,6,6-trimethyl-3-triethylsilanyloxy-cyclohex-1-enyl)-penta-2,4-dienenitrile 
• 228120-14-7 (2E,4E)-3-Methyl-5-(2,6,6-trimethyl-3-triethylsilanyloxy-cyclohex-1-enyl)-penta-2,4-dienal 
• 228120-16-9 (E)-4-(2,6,6-Trimethyl-3-triethylsilanyloxy-cyclohex-1-enyl)-but-3-en-2-one 
• 14398-34-6 4-(3-hydroxy-2,6,6-trimethylcyclohex-1-enyl)but-3-en-2-one 
• 41891-54-7 diethyl 3-(ethoxycarbonyl)-3-methylprop-2-en-yl phosphate 
• 110890-64-7 3-ethynyl-2,4,4-trimethylcyclohex-2-en-1-one 
• 20013-73-4 2,6,6-trimethylcyclohex-2-en-1-one 
• 817203-16-0 rac-2,6,6-trimethyl-1-(trimethylsilylethynyl)cyclohex-2-en-1-ol 

Downstream Products

• 191171-86-5 6-diazo-3-[(1E,3E,5Z,7E)-8-formyl-3,7-dimethylnona-1,3,5,7-tetraenyl]-2,4,4-trimethylcyclohex-2-en-1-one 
• 129467-11-4 3-[(1E,3E,5E,7E)-9-(tert-Butyl-dimethyl-silanyloxy)-3,7-dimethyl-nona-1,3,5,7-tetraenyl]-2,4,4-trimethyl-cyclohex-2-enone 
• 129467-10-3 6-Diazo-3-((1E,3E,5E,7E)-9-hydroxy-3,7-dimethyl-nona-1,3,5,7-tetraenyl)-2,4,4-trimethyl-cyclohex-2-enone 
• 129467-08-9 6-diazo-3-[(1E,3E,5E,7Z)-8-formyl-3,7-dimethylnona-1,3,5,7-tetraenyl]-2,4,4-trimethylcyclohex-2-en-1-one 
• 71423-69-3 4-keto-13-cis-retinal 
• 33532-44-4 4-keto-all-trans-retinal 

Relevant articles and documents

Catalytic activities of tumor-specific human cytochrome P450 CYP2W1 toward endogenous substrates

CYP2W1 is a recently discovered human cytochrome P450 enzyme with a distinctive tumor-specific expression pattern. We show here that CYP2W1 exhibits tight binding affinities for retinoids, which have lownanomolar binding constants, andmuch poorer binding constants in the micromolar range for four other ligands. CYP2W1 converts alltrans retinoic acid (atRA) to 4-hydroxy atRA and all-Trans retinol to 4-OH all-Trans retinol, and it also oxidizes retinal. The enzyme much less efficiently oxidizes 17b-estradiol to 2-hydroxy-(17b)-estradiol and farnesol to a monohydroxylated product; arachidonic acid is, at best, a negligible substrate. These findings indicate that CYP2W1 probably plays an important role in localized retinoid metabolism that may be intimately linked to its involvement in tumor development.

Regulating gene expression using retinoids with Ch2 OH or related groups at the side chain terminal position

For the first time, certain retinoids with a side chain terminal CH2 OH group or ester or ether thereof or aldehyde rather than a side chain terminal COOH group and substitution at the 4-position have been indicated to bind to nuclear receptors

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