9-cis-Retinoic acid (CAS 5300-03-8)

5.0(1)

Alternate Names: 9-cis-Retinoic acid is also known as Alitretinoin.

Application: 9-cis-Retinoic acid is a Cox-2 inhibitor that prevents cell proliferation and induces cell differentiation.

CAS Number: 5300-03-8

Purity: ≥98%

Molecular Weight: 300.44

Molecular Formula: C₂₀H₂₈O₂

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

* Refer to Certificate of Analysis for lot specific data (including water content).

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9-cis-Retinoic acid is a vitamin A analog that inhibits cell proliferation and induces cell differentiation. 9-cis-Retinoic acid is an inhibitor of Cox-2 and an activator of RAR α, RAR β, RAR γ and RXR. 9-cis-Retinoic acid potently activates all isoforms of retinoic acid receptor. 9-cis-Retinoic. 9-cis-Retinoic acid can start a chain of effects beginning with the heterodimerization with retinoid X receptor isoforms, and then homodimerization in addition to heterodimerization with between RXR and other partners.

References

1. Kane, M.A.Analysis, occurrence, and function of 9-cis-retinoic acid. Biochimica et Biophysica Acta 1821(1), 10-20 (2012).
2. Wong, M.F., Repa, J.J., Clagett-Dame, M., et al.Synthesis and receptor binding affinity of conformationally restricted retinoic acid analogues. Bioorganic & Medicinal Chemistry Letters 7(17), 2313-2318 (1997).
3. Umemiya, H., Fukasawa, H., Ebisawa, M., et al.Regulation of retinoidal actions by diazepinylbenzoic acids. Retinoid synergists which activate the RXR-RAR heterodimers. Journal of Medicinal Chemistry 40(26), 4222-4234 (1997).
4. Dawson, M.I., and Xia, Z.The retinoid X receptors and their ligands. Biochim Biophys.Acta. 1821(1), 21-56 (2012).
5. Zheng, Y. et al. 1997. Carcinogenesis. 18(11): 2119-2125. PMID: 9395211

Physical State :

Solid

Solubility :

Soluble in chloroform (50 mg/ml), DMSO (~25 mg/ml), ethanol (25 mg/ml), and acetone (25 mg/ml). Insoluble in water.

Storage :

Store at -20° C

Melting Point :

178-180° C

Boiling Point :

462.80° C at 760 mmHg (Predicted)

Density :

1.01 g/cm³ (Predicted)

Refractive Index :

n²⁰_D 1.56 (Predicted)

IC50 :

RXR γ: IC₅₀ = 4 nM (human); RAR α: IC₅₀ = 7 nM (human); RAR β: IC₅₀ = 7 nM (human); RXR β: IC₅₀ = 12 nM (human); RAR γ: IC₅₀ = 17 nM (human)

Ki Data :

RAR β: K_i= 0.5 nM (human); RAR γ: K_i= 1 nM (human); RXR β: K_i= 3.8 nM (human); RXR α: K_i= 8 nM (human); RXR γ: K_i= 11 nM (human)

pK Values :

pK_a: 4.73 (Predicted)

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

WGK Germany :

RTECS :

VH6450000

PubChem CID :

449171

Merck Index :

14: 249

MDL Number :

MFCD00270072

SMILES :

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

Download SDS (MSDS)

Certificate of Analysis

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9-cis-Retinoic acid (CAS 5300-03-8) Product Citations

See how others have used 9-cis-Retinoic acid (CAS 5300-03-8). Click on the entry to view the PubMed entry .

Citations 1 to 6 of 6 total

PMID: # 29072505 Pastorková, B. et al. 2017. Drug Chem Toxicol. 41: 1-7.

PMID: # 26898150 Venne, P. et al. 2016. J Chromatogr A. 1438: 57-64.

PMID: # 26208032 Illés, P. et al. 2015. J. Agric. Food Chem. 63: 7074-83.

PMID: # 24971931 Paquette, MA.|Atlas, E.|Wade, MG.|Yauk, CL.| et al. 2014. PLoS One. 9: e101155.

PMID: # 33055159 Sci Adv.

PMID: # 31231034 Immunity. 119-130.e5.

Citations 1 to 6 of 6 total

Rated 5 out of 5 by SS from Szab Szab , DR. et al. (PubMed 23807211) found that 9-cis-Retinoic acid, a Cox-2 inhibitor that prevents cell proliferation and induces cell differentiation, significantly decreased cell viability and steroid hormone secretion in a concentration- and time-dependent manner in the NCI-H295R cell line. -SCBT Publication Review

Date published: 2015-06-29

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