A metabolite of all-trans retinoic acid
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Parent Compound(s)
11017all-trans Retinoic Acid
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all-trans-4-hydroxy Retinoic Acid

Item No. 21378

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-hydroxy-retinoic acid
CAS Number
66592-72-1
Synonyms
  • 4-hydroxy atRA
  • 4-hydroxy RA
Molecular Formula
C20H28O3
Formula Weight
316.4
Purity
≥90%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Slightly solubleMethanol: Slightly soluble
SMILES
CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(O)=O)C(C)(C)CCC1O
InChi Code
InChI=1S/C20H28O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13,18,21H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+
InChi Key
KGUMXGDKXYTTEY-FRCNGJHJSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    1 mg

    $439

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    Product Description

    all-trans-4-hydroxy Retinoic acid is a metabolite of all-trans retinoic acid (Item No. 11017) formed by the cytochrome P450 (CYP) isoforms CYP26A1, B1, and C1.1,2 It binds to retinoic acid receptors (RARs) with a lower affinity than other all-trans retinoic acid metabolites (IC50s = 606, 298, and 892 nM for RARα, RARβ, and RARγ, respectively, in a radioligand binding assay). It also transactivates RARs with a lower efficacy than other metabolites (EC50s = 791, 64, and 94 nM for RARα, RARβ, and RARγ, respectively) but induces transcription of a reporter plasmid equipotently. all-trans-4-hydroxy Retinoic acid inhibits cell growth, halts the cell cycle in the G1 phase, and induces differentiation of NB4 acute promyelocytic leukemia cells (EC50 = 79.8 nM).3

    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. Taimi, M., Helvig, C., Wisniewski, J., et al. A novel human cytochrome P450, CYP26C1, involved in metabolism of 9-cis and all-trans isomers of retinoic acid. The Journal of Biological Chemisty 279(1), 77-85 (2004).

    3. Idres, N., Benoît, G., Flexor, M.A., et al. Granulocytic differentiation of human NB4 promyelocytic leukemia cells induced by all-trans retinoic acid metabolites. Cancer Res. 61(2), 700-705 (2001).