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 (6)
Reviews
Protocols (2)
Literature (3)

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.

Motor neurons differentiated from hiPSCs using Retinoic Acid

iPS differentiation with Retinoic Acid

Image shows IBJ6 human fibroblast induced pluripotent stem cells which have been differentiated into motor neurons. This was performed using a combination of LDN 193189 (100 nM) (Cat. No. 6053) and SB 431542 (Cat. No. 1614) followed by Retinoic acid and Purmorphamine (Cat. No. 4551) culture on Laminin for 18 days. Commitment to the motor neuron fate was assessed using the motor neuron marker anti-Human Islet-1 (red, R&D Systems®, Cat. No. AF1837) and the general neuronal marker, beta III tubulin (green, R&D Systems®, Cat. No. MAB1195). For visualization, the neurons were stained using Northernlights™ 557-conjugated Donkey anti-Goat Secondary Antibody (R&D Systems®, Cat. No. NL001) and Northernlights™ 493-conjugated Donkey anti-Mouse Secondary Antibody (R&D Systems®, Cat. No. NL009) and counterstained with DAPI (blue, Cat. No. 5748).

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

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 25
ethanol 3 10

Preparing Stock Solutions

The following data is based on the product molecular weight 300.44. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
0.25 mM 13.31 mL 66.57 mL 133.14 mL
1.25 mM 2.66 mL 13.31 mL 26.63 mL
2.5 mM 1.33 mL 6.66 mL 13.31 mL
12.5 mM 0.27 mL 1.33 mL 2.66 mL

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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

Lancaster et al (2015) Generation of Cerebral Organoids from Human Pluripotent Stem Cells Nat. Protoc. 9 2329 PMID: 25188634

Kadoshima et al (2013) Self-organization of axial polarity, inside-out layer pattern, and species-specific progenitor dynamics in human ES cell-derived neocortex. Proc.Natl.Acad.Sci.USA. 110 20284 PMID: 24277810


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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, Organoids, 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

6 Citations for Retinoic acid

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

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

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

Li et al (2018) Fast Generation of Functional Subtype Astrocytes from Human Pluripotent Stem Cells. Stem Cell Reports 11 998 PMID: 30269954


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Protocols for Retinoic acid

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

Literature in this Area

Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* your copy today!

*Please note that Tocris will only send literature to established scientific business / institute addresses.


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