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

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)
Molecular Weight:	300.44

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.

Retinoic acid synthesized to Ancillary Material Grade also available.

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

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 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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References for Retinoic acid

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

Sanjurjo-Soriano Retinoic acid delays initial photoreceptor differentiation and results in a highly structured mature retinal organoid. Stem Cell Res.Ther. 2022 PMID: 36114559
Tao and Zhang Neural subtype specification from human pluripotent stem cells. Cell Stem Cell 2016 PMID: 27814479
Alekseenko Robust derivation of transplantable dopamine neurons from human pluripotent stem cells by timed retinoic acid delivery. Nat.Commun. 2022 PMID: 35650213
Lancaster Generation of Cerebral Organoids from Human Pluripotent Stem Cells Nat.Protoc. 2015 PMID: 25188634
Kadoshima 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 PMID: 24277810
Galluzzi Pharmacological modulation of autophagy: therapeutic potential and persisting obstacles. Nat.Rev.Drug.Discov. 2017 PMID: 28529316
Stehlin-Gaon All-trans retinoic acid is a ligand for the orphan nuclear receptor RORβ. Nat.Struct.Biol. 2003 PMID: 12958591
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 PMID: 8185324
Dani Differentiation of embryonic stem cells into adipocytes in vitro. J. Cell Sci. 1997 PMID: 9202388
Apfel A retinoic acid receptor alpha antagonist selectively counteracts retinoic acid effects. Proc.Natl.Acad.Sci.U.S.A. 1992 PMID: 1323127

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