Retinoic acid

Retinoic acid is a metabolite of vitamin A that plays important roles in cell growth, differentiation, and organogenesis. Retinoic acid is a natural agonist of RAR nuclear receptors, with IC50s of 14 nM for RARα/β/γ. Retinoic acid bind to PPARβ/δ with Kd of 17 nM. Retinoic acid acts as an inhibitor of transcription factor Nrf2 through activation of retinoic acid receptor alpha.

Product Specifications

CAS Number

[302-79-4]

Product Name Alternative

Vitamin A acid; all-trans-Retinoic acid; ATRA

UNSPSC

12352211

Hazard Statement

H302, H315, H360, H410

Target

Autophagy; Endogenous Metabolite; Organoid; PPAR; RAR/RXR

Type

Natural Products

Related Pathways

Autophagy; Cell Cycle/DNA Damage; Metabolic Enzyme/Protease; Stem Cell/Wnt; Vitamin D Related/Nuclear Receptor

Applications

Cancer-programmed cell death

Field of Research

Cancer; Inflammation/Immunology; Metabolic Disease; Neurological Disease

Assay Protocol

https://www.medchemexpress.com/Retinoic-acid.html

Purity

99.81

Solubility

DMSO : 50 mg/mL (ultrasonic; warming; heat to 60°C)

Smiles

CC1(C)C(/C=C/C(C)=C/C=C/C(C)=C/C(O)=O)=C(C)CCC1

Molecular Formula

C20H28O2

Molecular Weight

300.44

Precautions

H302, H315, H360, H410

References & Citations

[1]Wu L, et al. Retinoid X Receptor Agonists Upregulate Genes Responsible for the Biosynthesis of All-Trans-Retinoic Acid in Human Epidermis. PLoS One. 2016 Apr 14;11 (4) :e0153556.|[2]Shaw N, et al. Retinoic acid is a high affinity selective ligand for the peroxisome proliferator-activated receptor beta/delta. J Biol Chem. 2003 Oct 24;278 (43) :41589-92.|[3]Yu S, et al. Retinoic acid induces neurogenesis by activating both retinoic acid receptors (RARs) and peroxisomeproliferator-activated receptor β/δ (PPARβ/δ) . J Biol Chem. 2012 Dec 7;287 (50) :42195-205.|[4]Kam RK, et al. Retinoic acid synthesis and functions in early embryonic development. Cell Biosci. 2012 Mar 22;2 (1) :11.|[5]Apfel C, et al. A retinoic acid receptor alpha antagonist selectively counteracts retinoic acid effects. Proc Natl Acad Sci U S A. 1992 Aug 1;89 (15) :7129-33.|[6]Xiu Jun Wang, et al. Identification of retinoic acid as an inhibitor of transcription factor Nrf2 through activation of retinoic acid receptor alpha. Proc Natl Acad Sci U S A. 2007 Dec 4;104 (49) :19589-94.