16α-Hydroxyestrone
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16α-Hydroxyestrone
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CAS No:
566-76-7
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Formula:
C18H22O3
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Chemical Name:
16α-Hydroxyestrone
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Synonyms:
Estra-1,3,5(10)-trien-17-one,3,16-dihydroxy-,(16α)-;Estra-1,3,5(10)-trien-17-one,3,16α-dihydroxy-;(16α)-3,16-Dihydroxyestra-1,3,5(10)-trien-17-one;16α-Hydroxyestrone;3,16α-Dihydroxy-1,3,5(10)-estratrien-17-one;Estra-1,3,5(10)-triene-3,16α-diol-17-one
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CAS No:
Description
Pale Pink Solid
Solid
16alpha-hydroxyestrone is the 16alpha-hydroxy derivative of estrone; a minor estrogen metabolite. It has a role as a mouse metabolite, a human blood serum metabolite, an estrogen and a human urinary metabolite. It is a 16alpha-hydroxy steroid, a secondary alpha-hydroxy ketone, a 3-hydroxy steroid and a 17-oxo steroid. It derives from an estrone.|16alpha-Hydroxyestrone is a metabolite formed during the catabolism of estrone by the liver through the hydroxylation of the carbon at position 16 by cytochrome P450 (CYP) family enzymes, including CYP3A4 and 3A5, with potential carcinogenic activity. With increased estrogenic activity compared to the parent compound, 16alpha-hydroxyestrone (16alpha-OHE1) increases the expression of ER-responsive genes, which leads to increased proliferation of susceptible tumor cells. The ratio between the two estrogen metabolites, 2-hydroxyestrone (2-OHE1), a weak estrogen and metabolite from the 2-hydroxylation pathway, and 16alpha-OHE1, a metabolite from the 16-hydroxylation pathway, may be used to assess the risk of certain cancers; a higher ratio of 2-OHE1:16alpha-OHE1 correlates with decreased cancer risk.
Characteristics
57.53000
2.32
Solid
1.3±0.1 g/cm3
214 °C
493.2±45.0 °C at 760 mmHg
266.2±25.2 °C
1.612
-20ºC Freezer
Safety Information
3
R40
S22-S36
Xn
P201, P202, P281, P308+P313, P405, P501
H351
|Warning|H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]|P201, P202, P281, P308+P313, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory.
16α-Hydroxyestrone Use and Manufacturing
A major metabolite of Estradiol
Lipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C18 steroids (estrogens) and derivatives [ST0201]
Computed Properties
Molecular Weight:286.4
XLogP3:2.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Exact Mass:286.15689456
Monoisotopic Mass:286.15689456
Topological Polar Surface Area:57.5
Heavy Atom Count:21
Complexity:448
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes