2-Methoxyestrone
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2-Methoxyestrone
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CAS No:
362-08-3
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Formula:
C19H24O3
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Chemical Name:
2-Methoxyestrone
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Synonyms:
Estra-1,3,5(10)-trien-17-one,3-hydroxy-2-methoxy-;Estrone,2-methoxy-;3-Hydroxy-2-methoxyestra-1,3,5(10)-trien-17-one;2-Methoxyestrone;2-Hydroxyestrone 2-methyl ether;GSS 33;2-Methoxy-3-hydroxyestra-1,3,5(10)-trien-17-one;2-Methoxy-17-oxoestra-1,3,5(10)-trien-3-ol
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CAS No:
Description
2-Methoxyestrone is a methoxylated catechol estrogen and metabolite of estrone, with a pKa of 10.81.
Solid
2-methoxyestrone is a 17-oxo steroid that is estrone in which the hydrogen at position 2 has been replaced by a methoxy group. It has a role as a human metabolite and a mouse metabolite. It is a 3-hydroxy steroid, a 17-oxo steroid, an alicyclic ketone, a member of phenols, an aromatic ether and a phenolic steroid. It derives from an estrone.|2-Methoxyestrone is a metabolite formed during the methylation of 2-hydroxyestrone (2-OHE1) by catechol-O-methyltransferase (COMT), with potential anticarcinogenic and minimal estrogen activities. The mechanism of action for the antitumor activity of 2-methoxyestrone (2-OMeE1) is not known. A high 2-methoxyestrone (2-OMeE1)/2-OHE1 ratio indicates higher methylation efficiency and correlates with a lower cancer risk.
Characteristics
46.5
3.39
Solid
1.2±0.1 g/cm3
187.0-189.5 °C
463.5±45.0 °C at 760 mmHg
165.9±22.2 °C
1.576
174.47 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]|201.71 Ų [M+Na]+ [CCS Type: DT, Method: stepped-field]|184.55 Ų [M-H]- [CCS Type: DT, Method: stepped-field]|183.9 Ų [M-H]-
Safety Information
UN3077 9/PG 3
3
40-50/53
22-36-61-60
Xn: Harmful;N: Dangerous for the environment;
P273-P281-P501
H351-H410
Drug Information
2-Methoxyestrone has known human metabolites that include (8R,9S,13S,14S)-2-Methoxy-13-methyl-3-[(2R,3R,4S,5S,6S)-3,4,5,6-tetrahydroxyoxan-2-yl]oxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one.
2-methoxyestrone
2-Methoxyestrone Use and Manufacturing
2-Methoxyestrone is a endogenous estrogen metabolite. 2-Methoxyestrone detection can be used as a breast cancer biomarker and help assess the risk-factors for development of breast cancer.
Lipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C18 steroids (estrogens) and derivatives [ST0201]
Computed Properties
Molecular Weight:300.4
XLogP3:3.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:300.17254462
Monoisotopic Mass:300.17254462
Topological Polar Surface Area:46.5
Heavy Atom Count:22
Complexity:462
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes