Retinoic acid

Catalog # Availability Size / Price Qty
0695/50
Retinoic acid | CAS No. 302-79-4 | Retinoic Acid Receptor Agonists
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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%

Product Details
Citations (6)
Reviews

Biological Activity

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.

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

M.Wt:
300.44
Formula:
C20H28O2
Solubility:
Soluble to 25 mM in DMSO and to 10 mM in ethanol
Purity:
≥98%
Storage:
Store at -20°C
CAS No:
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.

Background References

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

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⚠ 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

Citations for Retinoic acid

The citations listed below are publications that use Tocris products. Selected citations for Retinoic acid include:

6 Citations: Showing 1 - 6

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