63531-93-1

Basic information

• Product Name: 18-Hydroxy-all-trans-retinoic acid
• Synonyms: (2E,4E,6E,8E)-3,7-Dimethyl-9-(2-hydroxymethyl-6,6-dimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraenoic acid;18-Hydroxy-all-trans-retinoic acid;18-Hydroxyretinoic acid;all-trans-18-Hydroxy Retinoic Acid;Ro 12-4825
• CAS NO: 63531-93-1
• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.43452
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Retinoids
• Mol File: 63531-93-1.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 514.3°C at 760 mmHg
• Flash Point: 278.9°C
• Appearance: /
• Density: 1.069g/cm³
• Vapor Pressure: 9.98E-13mmHg at 25°C
• Refractive Index: 1.57
• CAS DataBase Reference: 18-Hydroxy-all-trans-retinoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 18-Hydroxy-all-trans-retinoic acid(63531-93-1)
• EPA Substance Registry System: 18-Hydroxy-all-trans-retinoic acid(63531-93-1)

Safety Data

• Hazardous Substances Data: 63531-93-1(Hazardous Substances Data)

Usage

Description

18-Hydroxy-all-trans-retinoic acid is a hydroxylated metabolite of all-trans-Retinoic Acid (R250200), which is produced by the cytochrome P450 enzyme, CYP26C1. 18-Hydroxy-all-trans-retinoic acid plays a significant role in various biological processes and has potential applications in different industries.

Uses

Used in Pharmaceutical Industry:
18-Hydroxy-all-trans-retinoic acid is used as a pharmaceutical agent for its potential therapeutic effects. It is involved in the regulation of cell growth, differentiation, and apoptosis, making it a promising candidate for the treatment of various diseases, including cancer.
Used in Cosmetic Industry:
In the cosmetic industry, 18-Hydroxy-all-trans-retinoic acid is used as an active ingredient in anti-aging and skin care products. Its ability to regulate cell growth and differentiation contributes to the improvement of skin health and appearance, reducing the signs of aging and promoting skin rejuvenation.
Used in Research Applications:
18-Hydroxy-all-trans-retinoic acid is also used in research settings as a tool to study the mechanisms of action of retinoic acid and its role in various biological processes. This helps scientists to better understand the potential therapeutic applications of this compound and develop new treatments for various diseases.

InChI:InChI=1/C20H28O3/c1-15(7-5-8-16(2)13-19(22)23)10-11-18-17(14-21)9-6-12-20(18,3)4/h5,7-8,10-11,13,21H,6,9,12,14H2,1-4H3,(H,22,23)/b8-5+,11-10+,15-7-,16-13-

Upstream product

• 81121-51-9 (2E,4E,6E,8E)-9-[2-(1-Ethoxy-ethoxymethyl)-6,6-dimethyl-cyclohex-1-enyl]-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid 
• 81176-71-8 ethyl (2E,4E,6E,8E)-9-<2-(acetoxymethyl)-6,6-dimethyl-1-cyclohexen-1-yl>-3,7-dimethyl-2,4,6,8-nonatetraenoate 
• 65519-73-5 6-isopropoxymethylene-2,2-dimethyl-cyclohexanone 
• 76337-17-2 2-formyl-6,6-dimethylcyclohexanone 
• 81121-45-1 (E)-1-(2-Hydroxymethyl-6,6-dimethyl-cyclohex-1-enyl)-3-methyl-penta-1,4-dien-3-ol 
• 81121-44-0 rac-5-(6,6-dimethyl-2-formyl-1-cyclohexen-1-yl)-3-methyl-3-hydroxy-1-penten-4-yne 
• 81121-46-2 Acetic acid 2-((E)-3-hydroxy-3-methyl-penta-1,4-dienyl)-3,3-dimethyl-cyclohex-1-enylmethyl ester 
• 81121-50-8 (2E,4E,6E,8E)-9-[2-(1-Ethoxy-ethoxymethyl)-6,6-dimethyl-cyclohex-1-enyl]-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid ethyl ester 
• 86096-08-4 2-Formyl-6-methylcyclohexanone sodium salt 
• 81121-47-3 [(2E,4E)-5-(2-Acetoxymethyl-6,6-dimethyl-cyclohex-1-enyl)-3-methyl-penta-2,4-dienyl]-triphenyl-phosphonium; bromide 
• 81121-49-5 (2E,4E,6E,8E)-9-(2-Hydroxymethyl-6,6-dimethyl-cyclohex-1-enyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid ethyl ester 
• 81121-48-4 (2E,4Z,6E,8E)-9-(2-Acetoxymethyl-6,6-dimethyl-cyclohex-1-enyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid ethyl ester 
• 583-60-8 2-Methylcyclohexanone 
• 302-79-4 all-trans-retinoic-acid 

Relevant articles and documents

CYP26C1 is a hydroxylase of multiple active retinoids and interacts with cellular retinoic acid binding proteins

The clearance of retinoic acid (RA) and its metabolites is believed to be regulated by the CYP26 enzymes, but the specific roles of CYP26A1, CYP26B1, and CYP26C1 in clearing active vitamin A metabolites have not been defined. The goal of this study was to