Abcam, ab141023, 9-cis-Retinoic acid, Endogenous retinoic acid receptor agonist

Size: 1mg / 5mg
MW 300.4 Da, Purity >98%. High affinity, endogenous retinoic acid receptor (RAR) agonist (IC 50 = 14 nM for RARα, RARβ and RARγ). Active metabolite of vitamin A. Acts as a transcription factor to regulate the growth and differentiation of normal and malignant cells and capable of inhibiting prostaglandin-endoperoxide synthase 2 expression.
Key facts
CAS number:5300-03-8,
Purity:>98%,
Form:SolidSee storage information,
Molecular weight:300.4 Da,
Molecular formula:C20H28O2,
PubChem:449171,
Nature:Synthetic,
Solubility:Soluble in DMSO to 25 mMSoluble in ethanol to 25 mM,
Biochemical name:Alitretinoin,
Biological description:High affinity, endogenous retinoic acid receptor (RAR) agonist (IC50= 14 nM for RARα, RARβ and RARγ). Active metabolite of vitamin A. Acts as a transcription factor to regulate the growth and differentiation of normal and malignant cells and capable of inhibiting prostaglandin-endoperoxide synthase 2 expression.,
Canonical smiles:CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)O)C)C,
Isomeric smiles:CC1=C(C(CCC1)(C)C)/C=C/C(=C\C=C\C(=C\C(=O)O)\C)/C,
InChi:InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8-,16-14+,
InChiKey:SHGAZHPCJJPHSC-ZVCIMWCZSA-N,
IUPAC Name:(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid

Properties and Storage Information:
Shipped at conditions-Ambient - Can Ship with Ice, Appropriate short-term storage conditions--20°C, Appropriate long-term storage conditions--20°C, Storage information-It is important to note that this product is reported to be light sensitive, Store in the dark, Store under desiccating conditions, The product can be stored for up to 12 months

Supplementary Information:
This supplementary information is collated from multiple sources and compiled automatically.
The retinoic acid receptors and retinoid X receptors are part of a larger family of nuclear receptors that play main roles in gene expression. Retinoic acid receptor gamma (RARγ) NUR77 estrogen receptor (ER) LXR alpha (liver X receptor alpha) RXRG RAR alpha RAR beta RXRB RXRA and LXR beta are alternate names of these proteins. Masses of these proteins vary with RXRA for example around 55 kDa. These receptors are expressed in various tissues including the liver bone marrow and adipose tissue demonstrating broad physiological relevance.
Biological function summary
Retinoic acid receptors function by binding to retinoic acid and this binding influences gene transcription. Usually they form heterodimers with retinoid X receptors to perform their function more effectively. This complex modulates expression of genes involved in cell differentiation apoptosis and lipid metabolism. RAR and RXR proteins also interact with other nuclear receptors further influencing the regulation of key metabolic processes.
Pathways
Retinoic acid receptors and retinoid X receptors are critical in the retinoic acid signaling pathway and lipid metabolism pathways. In these pathways they closely associate with proteins such as PPARs (peroxisome proliferator-activated receptors) to coordinate regulation of genes linked to energy homeostasis. These specific interactions ensure the maintenance of normal cellular functions and contribute to the body's ability to adapt to nutritional and metabolic changes.
Disruptions in retinoic acid receptor and retinoid X receptor functions link to cancer and metabolic syndrome. Specifically abnormal expression or mutations in these receptors can drive the progression of acute promyelocytic leukemia and non-alcoholic fatty liver disease. The involvement of related proteins such as PPARs in these pathways further implicates the importance of maintaining proper function and regulation of these receptor families in disease prevention and management.