A metabolite of estrone
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4-hydroxy Estrone

Item No. 33696

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,4-dihydroxy-estra-1,3,5(10)-trien-17-one
CAS Number
3131-23-5
Synonyms
  • 4-hydroxy E1
  • 4-OHE1
Molecular Formula
C18H22O3
Formula Weight
286.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Slightly solubleEthanol: Slightly, sonicated
SMILES
C[C@@]12[C@](CCC2=O)([H])[C@@]3([H])[C@@](CC1)([H])C4=CC=C(O)C(O)=C4CC3
InChi Code
InChI=1S/C18H22O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h4,6,11-12,14,19,21H,2-3,5,7-9H2,1H3/t11-,12-,14+,18+/m1/s1
InChi Key
XQZVQQZZOVBNLU-QDTBLXIISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    5 mg

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    10 mg

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    25 mg

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    Product Description

    4-hydroxy Estrone is a metabolite of the endogenous estrogen estrone (Item No. 10006485).1 It is formed from estrone primarily by the cytochrome P450 (CYP) isoforms CYP1B1, CYP1A2, and CYP1A1. 4-hydroxy Estrone (5 µM) induces nuclear translocation of phosphorylated p53 and is protective against glutamate-induced oxidative death in HT22 hippocampal neuronal cells.2 It reduces neurodegeneration induced by kainic acid in the rat hippocampus and improves working memory in the Y-maze in rats when administered at a dose of 10 µg/animal. 4-hydroxy Estrone also inhibits proliferation of MCF-7 and MDA-MB-231 breast cancer cells with IC50 values of 30 and 38 µM, respectively.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Cribb, A.E., Knight, M.J., Dryer, D., et al. Role of polymorphic human cytochrome P450 enzymes in estrone oxidation. Cancer Epidemiol. Biomarkers Prev. 15(3), 551-558 (2006).

    2. Choi, H.J., Lee, A.J., Kang, K.S., et al. 4-Hydroxyestrone, an endogenous estrogen metabolite, can strongly protect neuronal cells against oxidative damage. Sci. Rep. 10(1), 7283 (2020).

    3. Seeger, H., Huober, J., Wallwiener, D., et al. Inhibition of human breast cancer cell proliferation with estradiol metabolites is as effective as with tamoxifen. Horm. Metab. Res. 36(5), 277-280 (2004).