Retinoic acid

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Cat.No. 0695 - Retinoic acid | C20H28O2 | CAS No. 302-79-4
Description: Endogenous retinoic acid receptor agonist
Alternative Names: Tretinoin, ATRA
Chemical Name: 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2E,4E,6E,8E,-nonatetraenoic acid
Purity: ≥99% (HPLC)
Datasheet
Citations (4)
Reviews
Protocols (1)
Literature

Biological Activity

Endogenous agonist for retinoic acid receptors (IC50 = 14 nM for RARα, RARβ and RARγ receptors). Also promotes differentiation of mouse embryonic stem cells (ESCs) into adipocytes, neurons and glia in vitro. Proposed ligand of RORβ (Kd = 280 nM). Activates autophagy.

Compound Libraries

Retinoic acid is also offered as part of the Tocriscreen Epigenetics Toolbox and Tocriscreen Stem Cell Toolbox. Find out more about compound libraries available from Tocris.

Technical Data

M. Wt 300.44
Formula C20H28O2
Storage Store at -20°C
Purity ≥99% (HPLC)
CAS Number 302-79-4
PubChem ID 444795
InChI Key SHGAZHPCJJPHSC-YCNIQYBTSA-N
Smiles CC(/C=C/C1=C(C)CCCC1(C)C)=C\C=C\C(C)=C\C(O)=O

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data

Solubility Soluble to 25 mM in DMSO and to 10 mM in ethanol

Product Datasheets

Certificate of Analysis / Product Datasheet
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References

References are publications that support the biological activity of the product.

Apfel et al (1992) A retinoic acid receptor alpha antagonist selectively counteracts retinoic acid effects. Proc.Natl.Acad.Sci.U.S.A. 89 7129 PMID: 1323127

Dani et al (1997) Differentiation of embryonic stem cells into adipocytes in vitro. J. Cell Sci. 110 1279 PMID: 9202388

Sanquer and Gilchrest (1994) Characterisation of human cellular retinoic acid binding proteins-1 and -2: ligand binding affinities and distribution in skin. Arch.Biochem.Biophys. 311 86 PMID: 8185324

Merck Index 12 8333

Stehlin-Gaon et al (2003) All-trans retinoic acid is a ligand for the orphan nuclear receptor RORβ. Nat.Struct.Biol. 10 820 PMID: 12958591

Galluzzi et al (2017) Pharmacological modulation of autophagy: therapeutic potential and persisting obstacles. Nat.Rev.Drug.Discov. PMID: 28529316


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Keywords: Retinoic acid, Retinoic acid supplier, Endogenous, retinoic, acid, receptor, agonists, modulates, PPARδ, PPARdelta, Positive, modulators, RAR, Retinoic, Acid, Receptors, RXR, Retinoid, X, Peroxisome, Proliferator-activating, PPAR, stem, cells, ATRA, all, trans, trans-retinoic, organoids, Tretinoin, Receptor, Acid-related, Orphan, ESCs, and, iPSC, Autophagy, 0695, Tocris Bioscience

⚠ WARNING: This product can expose you to chemicals including All-trans retinoic acid, which is known to the State of California to cause reproductive toxicity with developmental effects. For more information, go to www.P65Warnings.ca.gov

4 Citations for Retinoic acid

Citations are publications that use Tocris products. Selected citations for Retinoic acid include:

Bohnenpoll (2017) Retinoic acid signaling maintains epithelial and mesenchymal progenitors in the developing mouse ureter. Sci Rep 7 14803 PMID: 29093497

Han et al (2012) Berberine promotes axonal regeneration in injured nerves of the peripheral nervous system. Physiol Behav 15 413 PMID: 22316297

Davies et al (2012) Evolution and functional characterisation of melanopsins in a deep-sea chimaera (elephant shark, Callorhinchus milii). PLoS One 7 e51276 PMID: 23251480

Lewis et al (2015) Inhibition of PAD4 activity is sufficient to disrupt mouse and human NET formation. J Med Food 11 189 PMID: 25622091


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Reviews for Retinoic acid

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Protocols for Retinoic acid

The following protocol features additional information for the use of Retinoic acid (Cat. No. 0695).

Literature in this Area

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