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Submit ReviewRetinoic acid
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: ≥98% (HPLC)
Biological Activity for Retinoic acid
Retinoic acid is an endogenous agonist for retinoic acid receptors (IC50 = 14 nM for RARα, RARβ and RARγ receptors). Retinoic acid specifies anterior-posterior patterning of neural progenitors. It promotes differentiation of mouse embryonic stem cells (ESCs) into adipocytes, neurons and glia in vitro. Retinoic acid also promotes differentiation of human PSCs into dopaminergic neurons and maturation of retinal organoids. It is a proposed ligand of RORβ (Kd = 280 nM). Activates autophagy.
For more information about how Retinoic acid may be used, see our protocols: Generation of β cells from hPSCs, Cultivating Cerebral Organoids.
Retinoic acid synthesized to Ancillary Material Grade also available.
Scientific Data
IBJ6 human fibroblast induced pluripotent stem cells which have been differentiated into motor neurons. Performed using a combination of LDN 193189 (100 nM) (Catalog # 6053,Tocris) and SB 431542 (Catalog # 1614, Tocris) followed by Retinoic acid and Purmorphamine (Catalog # 4551, Tocris) culture on Laminin for 18 days. Commitment to the motor neuron fate was assessed using the motor neuron marker anti-Human Islet-1 (red, Catalog # AF1837, R&D Systems) and the general neuronal marker, beta III tubulin (green, Catalog # MAB1195, R&D Systems). For visualization, the neurons were stained using Northernlights™ 557-conjugated Donkey anti-Goat Secondary Antibody (Catalog # NL001, R&D Systems) and Northernlights™ 493-conjugated Donkey anti-Mouse Secondary Antibody (Catalog # NL009, R&D Systems) and counterstained with DAPI (blue, Catalog # 5748, Tocris).
Technical Data for Retinoic acid
| M. Wt | 300.44 |
| Formula | C20H28O2 |
| Storage | Store at -20°C |
| Purity | ≥98% (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 for Retinoic acid
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 7.51 | 25 | |
| ethanol | 3 | 10 |
Preparing Stock Solutions for Retinoic acid
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.
| 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 for Retinoic acid
References for Retinoic acid
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
Tao and Zhang (2016) Neural subtype specification from human pluripotent stem cells. Cell Stem Cell 19 573 PMID: 27814479
Alekseenko et al (2022) Robust derivation of transplantable dopamine neurons from human pluripotent stem cells by timed retinoic acid delivery. Nat.Commun. 13 3046 PMID: 35650213
Sanjurjo-Soriano et al (2022) Retinoic acid delays initial photoreceptor differentiation and results in a highly structured mature retinal organoid. Stem Cell Res.Ther. 13 478 PMID: 36114559
If you know of a relevant reference for Retinoic acid, please let us know.
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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, Autophagy, Organoids, Retinal, Stem, Cells, Neural, 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:
Bohnenpoll (2017) Retinoic acid signaling maintains epithelial and mesenchymal progenitors in the developing mouse ureter. Sci Rep 7 14803 PMID: 29093497
Lewis et al (2015) Inhibition of PAD4 activity is sufficient to disrupt mouse and human NET formation. J Med Food 11 189 PMID: 25622091
Jaako et al (2016) Prolyl endopeptidase is involved in the degradation of neural cell adhesion molecules in vitro. J Cell Sci 129 3792 PMID: 27566163
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
Li et al (2018) Fast Generation of Functional Subtype Astrocytes from Human Pluripotent Stem Cells. Stem Cell Reports 11 998 PMID: 30269954
Han et al (2012) Berberine promotes axonal regeneration in injured nerves of the peripheral nervous system. Physiol Behav 15 413 PMID: 22316297
Do you know of a great paper that uses Retinoic acid from Tocris? Please let us know.
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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.
Retinoid Receptors Scientific Review
Written by Alexander Moise, this review summarizes the nature of retinoid receptors, their isotype and isoform variants and modulation of retinoid signaling. Compounds available from Tocris are listed.