An agonist of RAR isoforms
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all-trans-5,6-epoxy Retinoic Acid

Item No. 22124

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5,6-epoxy-5,6-dihydro-retinoic acid
CAS Number
13100-69-1
Synonyms
  • 5,6-epoxy atRA
  • 5,6-epoxy RA
Molecular Formula
C20H28O3
Formula Weight
316.4
Purity
≥96%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: SolubleMethanol: Soluble
SMILES
CC1(O2)C2(/C=C/C(C)=C/C=C/C(C)=C/C(O)=O)C(C)(C)CCC1
InChi Code
InChI=1S/C20H28O3/c1-15(8-6-9-16(2)14-17(21)22)10-13-20-18(3,4)11-7-12-19(20,5)23-20/h6,8-10,13-14H,7,11-12H2,1-5H3,(H,21,22)/b9-6+,13-10+,15-8+,16-14+
InChi Key
KEEHJLBAOLGBJZ-WEDZBJJJSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    1 mg

    $385

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    Product Description

    all-trans-5,6-epoxy Retinoic acid (5,6-epoxy RA) is an agonist of all isoforms of the retinoic acid receptor (RAR; EC50s = 77, 35, and 4 nM for RARα, RARβ, and RARγ, respectively).1 5,6-epoxy RA (1 µM) also induces growth arrest of MCF-7 and NB4 cells in vitro.2,3 It is a natural metabolite of all-trans retinoic acid (Item No. 11017), which is a metabolite of vitamin A.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Idrest, N., Marill, J., Flexor, M.A., et al. Activation of retinoic acid receptor-dependent transcription by all-trans-retinoic acid metabolites and isomers. The Journal of Biological Chemisty 277(25), 31491-31498 (2002).

    2. Van heusden, J., Wouters, W., Ramaekers, F.C.S., et al. All-trans-retinoic acid metabolites significantly inhibit the proliferation of MCF-7 human breast cancer cells in vitro. Br. J. Cancer 77(1), 26-32 (1998).

    3. McCormick, A.M., and Napoli, J.L. Identification of 5,6-epoxyretinoic acid as an endogenous retinol metabolite. The Journal of Biological Chemisty 257(4), 1730-1735 (1982).