An active metabolite of all-trans retinoic acid
Related Products
Isomer(s)
343884-oxo Isotretinoin
Parent Compound(s)
11017all-trans Retinoic Acid
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4-oxo Retinoic Acid

Item No. 35819

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
CAS Number
38030-57-8
Synonyms
  • all-trans-4-keto Retinoic Acid
  • all-trans-4-oxo RA
  • all-trans-4-oxo Retinoic Acid
  • 4-keto atRA
  • 4-oxo RA
Molecular Formula
C20H26O3
Formula Weight
314.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Slightly solubleMethanol: Slightly soluble
λmax
280, 360 nm
SMILES
OC(/C=C(C)/C=C/C=C(C)/C=C/C(C(C)(CC1)C)=C(C)C1=O)=O
InChi Code
InChI=1S/C20H26O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+
InChi Key
GGCUJPCCTQNTJF-FRCNGJHJSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

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    25 mg

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    Product Description

    4-oxo Retinoic acid is an active metabolite of the vitamin A metabolite and retinoic acid receptor (RAR) ligand all-trans retinoic acid (Item No. 11017).1 It is formed from all-trans retinoic acid by several cytochrome P450 (CYP) isoforms, including CYP1A1, CYP3A7, and CYP26A1.2,3 4-oxo Retinoic acid binds to RARα, RARβ, and RARγ (IC50s = 59, 50, and 142 nM, respectively, in radioligand binding assays) and induces expression of a luciferase reporter in COS-7 cells expressing RARα, RARβ, or RARγ (EC50s = 33, 8, and 89 nM, respectively).1 It increases protein levels of cytokeratin 7 (CK-7) and CK-19 in human epidermal keratinocytes when used at a concentration of 1 µM.4 4-oxo Retinoic acid (10-1,000 nM) inhibits the proliferation of MCF-7 breast cancer cells.5 It is teratogenic to zebrafish embryos (EC50 = 8.1 nM).6

    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. Marill, J., Cresteil, T., Lanotte, M., et al. Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol. Pharmacol. 58(6), 1341-1348 (2000).

    3. Thatcher, J.E., Buttrick, B., Shaffer, S.A., et al. Substrate specificity and ligand interactions of CYP26A1, the human liver retinoic acid hydroxylase. Mol. Pharmacol. 80(2), 228-239 (2011).

    4. Baron, J.M., Heise, R., Blaner, W.S., et al. Retinoic acid and its 4-oxo metabolites are functionally active in human skin cells in vitro. J. Invest. Dermatol. 125(1), 143-153 (2005).

    5. 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).

    6. Pípal, M., Novák, J., Rafajová, A., et al. Teratogenicity of retinoids detected in surface waters in zebrafish embryos and its predictability by in vitro assays. Aquat. Toxicol. 246, 106151 (2022).