4-Hydroxyretinoic acid

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].

Product Specifications

CAS Number

[66592-72-1]

UNSPSC

12352211

Hazard Statement

H302, H315, H360, H410

Target

RAR/RXR

Type

Reference compound

Related Pathways

Metabolic Enzyme/Protease; Vitamin D Related/Nuclear Receptor

Applications

COVID-19-immunoregulation

Field of Research

Cancer; Inflammation/Immunology; Neurological Disease

Assay Protocol

https://www.medchemexpress.com/4-hydroxyretinoic-acid.html

Purity

95.11

Solubility

DMSO : 100 mg/mL (ultrasonic;warming;heat to 60°C)

Smiles

CC(/C=C/C=C(/C=C/C1=C(C(O)CCC(C)1C)C)C)=C\C(O)=O

Molecular Formula

C20H28O3

Molecular Weight

316.43

Precautions

H302, H315, H360, H410

References & Citations

[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.