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4-Hydroxyretinoic acid

Names

[ CAS No. ]:
66592-72-1

[ Name ]:
4-Hydroxyretinoic acid

[Synonym ]:
rac all-trans 4-Hydroxy Retinoic Acid

Biological Activity

[Description]:

4-Hydroxyretinoic acid (4-HRA) is a naturally occurring retinoid derivative with diverse biological effects. 4-Hydroxyretinoic acid is formed from retinol catalyzed by cytochrome P-450 isozyme(s), and is mainly metabolized by the liver in the body. 4-Hydroxyretinoic acid also serves as the substrate for human liver microsomal UDP-glucuronosyltransferase(s) and recombinant UGT2B7. 4-Hydroxyretinoic acid regulates gene expression and cell differentiation via binding to nuclear receptor RAR (Retinoic Acid Receptor), and activates RARs and RXR-alpha, to induce cancer cell apoptosis. In addition, 4-Hydroxyretinoic acid is also involved in various physiological processes such as immune regulation, neuroprotection, and anti-oxidation[1][2].

[Related Catalog]:

Research Areas >> Cancer
Research Areas >> Inflammation/Immunology
Research Areas >> Neurological Disease
Signaling Pathways >> Metabolic Enzyme/Protease >> RAR/RXR

[Target]

UDP-glucuronosyltransferase, cytochrome P-450 isozyme[1]; RAR, RXR-alpha[2]


[References]

[1]. Samokyszyn VM, et al. 4-hydroxyretinoic acid, a novel substrate for human liver microsomal UDP-glucuronosyltransferase(s) and recombinant UGT2B7. J Biol Chem. 2000 Mar 10;275(10):6908-14.  

[2]. Duell EA, et al. Human skin levels of retinoic acid and cytochrome P-450-derived 4-hydroxyretinoic acid after topical application of retinoic acid in vivo compared to concentrations required to stimulate retinoic acid receptor-mediated transcription in vitro. J Clin Invest. 1992 Oct;90(4):1269-74.  

Chemical & Physical Properties

[ Density]:
1.075g/cm3

[ Boiling Point ]:
506.5ºC at 760 mmHg

[ Molecular Formula ]:
C20H28O3

[ Molecular Weight ]:
316.43

[ Flash Point ]:
274.2ºC

[ Exact Mass ]:
316.20400

[ PSA ]:
57.53000

[ LogP ]:
4.57340

[ Index of Refraction ]:
1.574

Synthetic Route

Precursor & DownStream


Related Compounds