Retinoic acid

Name: Retinoic acid
Brand: Tocris Bioscience
SKU: 0695

Tocris Bioscience, part of Bio-Techne | Catalog # 0695

Citations (150)

COA / SDS

Endogenous retinoic acid receptor agonist

Key Product Details

Chemical Name:	3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2E,4E,6E,8E,-nonatetraenoic acid
Purity:	≥98%

View Full Technical Details for Retinoic acid

Technical Data
Citations

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 (K_d = 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.

Scientific Data Examples for Retinoic acid

	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

Formula	C₂₀H₂₈O₂
Storage	Store at -20°C
Purity	≥98%
CAS Number	302-79-4

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 for Retinoic acid

Solubility

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

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References for Retinoic acid

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

Kang, Minyong, Han, Yong-Mah Differentiation of human pluripotent stem cells into nephron progenitor cells in a serum and feeder free system. PLoS ONE, 2014;9(4):e94888. 2014 PMID: 24728509
Yang J, Wang J, Pan L, Li H, Rao C, Zhang X, Niu G, Qu J, Hou L BMP4 is required for the initial expression of MITF in melanocyte precursor differentiation from embryonic stem cells. Exp Cell Res, 2014;320(1):54-61. 2014 PMID: 24080013
Whelan J, Wang L, Chen J, Metts M, Nasser T, McGoldrick L, Bridges L Retinoids induce integrin-independent lymphocyte adhesion through RAR-alpha nuclear receptor activity. Biochem Biophys Res Commun, 2014;454(4):537-542. 2014 PMID: 25450689
Fox JT, Sakamuru S, Huang R High-throughput genotoxicity assay identifies antioxidants as inducers of DNA damage response and cell death. Proc. Natl. Acad. Sci. U.S.A., 2012;109(14):5423-8. 2012 PMID: 22431602
Galluzzi et al. Pharmacological modulation of autophagy: therapeutic potential and persisting obstacles. Nat.Rev.Drug.Discov., 2017; PMID: 28529316
Apfel et al. A retinoic acid receptor alpha antagonist selectively counteracts retinoic acid effects. Proc.Natl.Acad.Sci.U.S.A., 1992;89:7129 PMID: 1323127
Dani et al. Differentiation of embryonic stem cells into adipocytes in vitro. J. Cell Sci., 1997;110:1279 PMID: 9202388
Sanquer and Gilchrest Characterisation of human cellular retinoic acid binding proteins-1 and -2: ligand binding affinities and distribution in skin. Arch.Biochem.Biophys., 1994;311:86 PMID: 8185324
Lancaster et al. Generation of Cerebral Organoids from Human Pluripotent Stem Cells Nat.Protoc., 2015;9:2329 PMID: 25188634
Kadoshima et al. 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., 2013;110:20284 PMID: 24277810
Stehlin-Gaon et al. All-trans retinoic acid is a ligand for the orphan nuclear receptor RORβ. Nat.Struct.Biol., 2003;10:820 PMID: 12958591

Product Documents for Retinoic acid

COA

Certificate of Analysis

To download a Certificate of Analysis, please select a batch below.

SDS

⚠ 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