An active metabolite of estrone
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16-Ketoestradiol

Item No. 36033

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,17β-dihydroxy-estra-1,3,5(10)-trien-16-one
CAS Number
566-75-6
Synonyms
  • 16-keto E2
  • NSC 51169
  • 16-Oxoestradiol
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 solubleMethanol: Slightly soluble
SMILES
C[C@@]12[C@](CC([C@@H]2O)=O)([H])[C@@]3([H])[C@@](CC1)([H])C4=CC=C(O)C=C4CC3
InChi Code
InChI=1S/C18H22O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-15,17,19,21H,2,4,6-7,9H2,1H3/t13-,14-,15+,17+,18+/m1/s1
InChi Key
KJDGFQJCHFJTRH-YONAWACDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $390

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    Product Description

    16-Ketoestradiol is an active metabolite of the endogenous estrogen estrone (Item No. 10006485).1 It is formed from estrone via an estriol (Item No. 10006484) or a 16-epiestriol (Item No. 33455) intermediate by oxidation of the C-16 hydroxyl. 16-Ketoestradiol binds to estrogen receptor α (ERα) and ERβ with IC50 values of 112.2 and 50.1 nM for the human receptors, respectively.2 Intravaginal administration of 16-ketoestradiol increases vaginal epithelial thickness, stratification, and cornification in mice, indicating antiestrogenic activity.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Brinton, L.A., Trabert, B., Anderson, G.L., et al. Serum estrogens and estrogen metabolites and endometrial cancer risk among postmenopausal women. Cancer Epidemiol. Biomarkers Prev. 25(7), 1081-1089 (2016).

    2. Zhu, B.T., Han, G.-Z., Shim, J.-Y., et al. Quantitative structure-activity relationship of various endogenous estrogen metabolites for human estrogen receptor α and β subtypes: Insights into the structural determinants favoring a differential subtype binding. Endocrinology 147(9), 4132-4150 (2006).

    3. Martin, L. Dimethylstilbestrol and 16-oxo-estradiol: Anti-estrogens or estrogens? Steroids 13(1), 1-10 (1969).