Retinoic Acid, all trans An activator of RAR and RXR and used in stem cells

Retinoic Acid, all trans (CAS 302-79-4)

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Synonym: Vitamin A acid
Application: An activator of RAR and RXR and used in stem cells
CAS Number: 302-79-4
Purity: ≥98%
Molecular Weight: 300.4
Molecular Formula: C20H28O2
Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
* Refer to Certificate of Analysis for lot specific data (including water content).
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Retinoic Acid, all trans is the oxidized carboxylic acid form of retinol, known in the dietary context as Vitamin A. Retinal (sc-210778) is the aldehyde form of retinol required by the retina of the eye for light absorption and visual processing. Retinoic acid and the other retinoids are involved in a broad range of biological regulations, mediating differentiation, proliferation, and apoptosis. Binding of Retinoic Acid to the nuclear receptors RAR (retinoic acid receptor) and the RXR (retinoid X receptor) initiate signals for transcription and development. The intimate relationship between retinoids and cell cycle regulation has been implicated in suppression of oncogenic proliferation. Also available in a photoactivatable, caged form (sc-202089).


References

1. Leid, M., et al., 1992. Multiplicity generates diversity in the retinoic acid signalling pathways. Trends in biochemical sciences. 17(10): 427-33. PMID: 1333659
2. Allenby, G., et al., 1994. Binding of 9-cis-retinoic acid and all-trans-retinoic acid to retinoic acid receptors alpha, beta, and gamma. Retinoic acid receptor gamma binds all-trans-retinoic acid preferentially over 9-cis-retinoic acid. The Journal of biological chemistry. 269(24): 16689-95. PMID: 8206989
3. Napoli, J L., et al., 1996. Biochemical pathways of retinoid transport, metabolism, and signal transduction. Clinical immunology and immunopathology. 80(3 Pt 2): S52-62. PMID: 8811064
4. Bushue, Nathan., et al., 2010. Retinoid pathway and cancer therapeutics. Advanced drug delivery reviews. 62(13): 1285-98. PMID: 20654663

Physical State :
Solid
Solubility :
Soluble in DMSO (25 mg/mL), ethanol (10 mg/mL), acetate, DMF (20 mg/mL), dimethyl sulfoxide (25 mg/mL), chloroform (40 mg/mL), methanol, acetone (30 mg/mL), and dichloromethane. Insoluble in water, and ether. It is recommended that solutions be made fresh for each use.
Storage :
Store at -20° C
Melting Point :
180-181° C (lit.)
Boiling Point :
~462.80° C at 760 mmHg (Predicted)
Density :
1.01 g/cm3
Refractive Index :
n20D 1.56
IC50 :
Retinoic acid receptor gamma: IC50 = 0.62 nM (human); Retinoic acid receptor alpha: IC50 = 5 nM (mus musculus); Herpesvirus 4: IC50 = 15.4 nM (human)
Ki Data :
Retinoic acid receptor gamma: Ki= 0.7 nM (human); Retinoic acid receptor beta: Ki= 0.5 nM (human); Retinoic acid receptor alpha: Ki= 0.1 nM (human)
pK Values :
pKa: 4.73
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
2
RTECS :
VH6475000
PubChem CID :
444795
Merck Index :
14: 8165
MDL Number :
MFCD00001551
EC Number :
206-129-0
Beilstein Registry :
2057223
SMILES :
CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C

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Retinoic Acid, all trans  Product Citations

See how others have used Retinoic Acid, all trans. Click on the entry to view the PubMed entry .

Citations 1 to 10 of 11 total

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

PMID: # 26345577  Briceño, A. et al. 2016. Neurotox Res. 29: 381-93.

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

PMID: # 20547768  Apostolatos, H. et al. 2010. J Biol Chem. -.

PMID: # 20096012  Britschgi, A. et al. 2010. Br. J. Haematol. 149: 55-64.

PMID: # 18511453  Wang, C. et al. 2008. J. Biochem. 144: 313-321.

PMID: # 18280257  Kiningham, KK. et al. 2008. Free Radic. Biol. Med. 44: 1610-1616.

PMID: # 17596541  Soriano, AO. et al. 2007. Blood. 110: 2302-2308.

PMID: # 17283134  Ohnuma-Ishikawa, K. et al. 2007. Cancer Res. 67: 1019-1029.

PMID: # 17051635  Wu, N. et al. 2006. Proteomics. 6: 6095-6106.

Citations 1 to 10 of 11 total
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Rated 5 out of 5 by from Britschgi et al Britschgi et al. (PubMed ID 20096012) used all-trans retinoic acid (ATRA) to treat acute promyeolocytic leukemia by causing the downregulation of 67LR.
Date published: 2015-05-22
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