A hydroxylated metabolite of estrone
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16α-hydroxy Estrone

Item No. 15208

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,16α-dihydroxy-estra-1,3,5(10)-trien-17-one
CAS Number
566-76-7
Synonyms
  • 16α-hydroxy E1
  • 16α-OHE1
Molecular Formula
C18H22O3
Formula Weight
286.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS (pH 7.2) (1:5): 0.15 mg/mlDMSO: 20 mg/ml
λmax
281 nm
SMILES
O=C1[C@H](O)C[C@@]2([H])[C@]3([H])CCC4=CC(O)=CC=C4[C@@]3([H])CC[C@@]21C
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/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,18+/m1/s1
InChi Key
WPOCIZJTELRQMF-QFXBJFAPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    16α-hydroxy Estrone (16α-OHE1) is a hydroxylated metabolite of E1 as well as an interconversion product with E2.1,2 E1 is 16α-hydroxylated by cytochrome P450 (CYP) isoforms, including CYP1A1, CYP3A5, CYP3A4, and CYP3A7, with CYP3A5 being breast-specific.3 16α-OHE1 is sulphatized or glucuronidated before excretion.3 It is increased in rheumatoid arthritis and decreased by physical activity.1,2 Unlike the parent estrogens and other hydroxylated metabolites of E1, 16α-OHE1 binds covalently and persistently activates estrogen receptors.4 In addition, this metabolite increases cell proliferation and does not suppress TNF-α secretion, whereas other estrogen metabolites are not pro-proliferative and have marked effects on TNF-α secretion.1,3 The levels of 16α-OHE1 are increased in some forms of hormone therapy.5 Because hormone therapy increases breast cancer risk, 16α-OHE1 has been implicated as a risk factor for breast cancer, although supportive data remains elusive.6,3,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Cutolo, M., Sulli, A., and Straub, R.H. Estrogen metabolism and autoimmunity. Autoimmun. Rev. 11(6-7), A460-A464 (2012).

    2. Matthews, C.E., Fortner, R.T., Xu, X., et al. Association between physical activity and urinary estrogens and estrogen metabolites in premenopausal women. J. Clin. Endocrinol. Metab. 97(10), 3724-3733 (2012).

    3. Obi, N., Wrieling, A., Heinz, J., et al. Estrogen metabolite ratio: Is the 2-hydroxyestrone to 16α-hydroxyestrone ratio predictive for breast cancer? Int. J. Womens Health 3, 37-51 (2011).

    4. Swaneck, G.E., and Fishman, J. Covalent binding of the endogenous estrogen 16α-hydroxyestrone to estradiol receptor in human breast cancer cells: Characterization and intranuclear localization. Proc. Natl. Acad. Sci. USA 85(21), 7831-7835 (1988).

    5. Mackey, R.H., Fanelli, T.J., Modugno, F., et al. Hormone therapy, estrogen metabolism, and risk of breast cancer in the women’s health initiative hormone therapy trial. Cancer Epidemiol. Biomarkers Prev. 21(11), 2022-2032 (2012).

    6. Okobia, M.N., and Bunker, C.H. Estrogen metabolism and breast cancer risk: A review. Afr. J. Reprod. Health 10(1), 13-25 (2006).