| Identification | Back Directory | [Name]
1,3,5[10]-ESTRATRIENE-3,16ALPHA-DIOL-17-ONE | [CAS]
566-76-7 | [Synonyms]
C05300
16α-OHE1
16A-hydroxyestrone
Estriol Impurity H
16α-hydroxy Estrone
Hydroxyestrone, 16α-
Estriol EP Impurity H
16ALPHA-HYDROXYESTRONE
16ALPHA-HYDROXYESTERONE
16α-Hydroxyestrone (solution)
Conjugated Estrogens EP Impurity H
16α-Hydroxyestrone Solution, 100ppm
16α-Hydroxyestrone Solution, 100ppm
1,3,5(10)-Estratriene-3,16α-diol-17-one
Estra-1,3,5(10)-triene-3,16α-diol-17-one
Estra-1,3,5(10)-triene-3,16a-diol-17-one
Estriol Impurity 8 (Estriol EP Impurity H)
3,16a-Dihydroxy-1,3,5(10)-estratrien-17-one
1,3,5[10]-ESTRATRIENE-3,16ALPHA-DIOL-17-ONE
1,3,5(10)-ESTRATRIEN-3,16-ALPHA-DIOL-17-ONE
3,16α-Dihydroxy-1,3,5(10)-estratrien-17-one
3,16ALPHA-DIHYDROXY-1,3,5[10]-ESTRATRIEN-17-ONE
(16a)-3,16-Dihydroxyestra-1,3,5(10)-trien-17-one
(16α)-3,16-Dihydroxyestra-1,3,5(10)-trien-17-one
(16R)-3,16α-Dihydroxy-1,3,5(10)-estratriene-17-one
Estra-1,3,5(10)-trien-17-one, 3,16-dihydroxy-, (16α)-
(8R,9S,13S,14S,16R)-3,16-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
(8R,9S,13S,14S,16R)-3,16-Dihydroxy-13-methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-one | [Molecular Formula]
C18H22O3 | [MDL Number]
MFCD00870436 | [MOL File]
566-76-7.mol | [Molecular Weight]
286.37 |
| Chemical Properties | Back Directory | [Melting point ]
209-211°C | [Boiling point ]
493.2±45.0 °C(Predicted) | [density ]
1.249±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C Freezer | [solubility ]
DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
10.23±0.60(Predicted) | [color ]
White to Light Beige |
| Hazard Information | Back Directory | [Description]
The naturally-occurring estrogens are estrone (E1, ), estradiol (E2, ), and estriol (E3, ). 16α-hydroxy Estrone (16α-OHE1) is a hydroxylated metabolite of E1 as well as an interconversion product with E2. E1 is 16α-hydroxylated by cytochrome P450 (CYP) isoforms, including CYP1A1, CYP3A5, CYP3A4, and CYP3A7, with CYP3A5 being breast-specific. 16α-OHE1 is sulphatized or glucuronidated before excretion. It is increased in rheumatoid arthritis and decreased by physical activity. Unlike the parent estrogens and other hydroxylated metabolites of E1, 16α-OHE1 binds covalently and persistently activates estrogen receptors. 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. The levels of 16α-OHE1 are increased in some forms of hormone therapy. Because hormone therapy increases breast cancer risk, 16α-OHE1 has been implicated as a risk factor for breast cancer, although supportive data remains elusive. | [Chemical Properties]
Pale Pink Solid | [Uses]
16α-Hydroxy Estrone (Estriol EP Impurity H) is a major metabolite of Estradiol. | [Uses]
A major metabolite of Estradiol | [Definition]
ChEBI: The 16alpha-hydroxy derivative of estrone; a minor estrogen metabolite. | [IC 50]
Human Endogenous Metabolite | [References]
[1] MAURIZIO CUTOLO Rainer H S Alberto Sulli. Estrogen metabolism and autoimmunity[J]. Autoimmunity reviews, 2012, 11 6: Pages A460-A464. DOI: 10.1016/j.autrev.2011.11.014
[2] CHARLES E MATTHEWS. Association between physical activity and urinary estrogens and estrogen metabolites in premenopausal women.[J]. Journal of Clinical Endocrinology & Metabolism, 2012, 97 10: 3724-3733. DOI: 10.1210/jc.2012-1732
[3] NADIA OBI. Estrogen metabolite ratio: Is the 2-hydroxyestrone to 16α-hydroxyestrone ratio predictive for breast cancer?[J]. International Journal of Women’s Health, 2011, 3: 37-51. DOI: 10.2147/ijwh.s7595
[4] G E SWANECK J F. Covalent binding of the endogenous estrogen 16 alpha-hydroxyestrone to estradiol receptor in human breast cancer cells: characterization and intranuclear localization.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1988, 85 21: 7831-7835. DOI: 10.1073/pnas.85.21.7831
[5] RACHEL H MACKEY. Hormone therapy, estrogen metabolism, and risk of breast cancer in the Women’s Health Initiative Hormone Therapy Trial.[J]. Cancer epidemiology, biomarkers & prevention?: a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology, 2012: 2022-2032. DOI: 10.1158/1055-9965.epi-12-0759
[6] M N OKOBIA C H B. Estrogen metabolism and breast cancer risk–a review.[J]. African journal of reproductive health, 2006, 10 1: 13-25.
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