2-Hydroxyestrone

2-Hydroxyestrone
Names
	IUPAC name (8R,9S,13S,14S)-2,3-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
	Other names 2-OHE1; 2,3-Dihydroxyestra-1,3,5(10)-trien-17-one; Estra-1,3,5(10)-trien-2,3-diol-17-one
Identifiers
CAS Number	362-06-1;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:1156;
ChEMBL	ChEMBL1627343;
ChemSpider	389514;
ECHA InfoCard	100.164.607
KEGG	C05298;
PubChem CID	440623;
UNII	UQS3A06ILY;
CompTox Dashboard (EPA)	DTXSID80904315 ;
	InChI InChI=1S/C18H22O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,19-20H,2-7H2,1H3/t11-,12+,14-,18-/m0/s1 Key: SWINWPBPEKHUOD-JPVZDGGYSA-N;
	SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=CC(=C(C=C34)O)O;
Properties
Chemical formula	C18H22O3
Molar mass	286.371 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2-Hydroxyestrone (2-OHE1), also known as estra-1,3,5(10)-trien-2,3-diol-17-one, is an endogenous, naturally occurring catechol estrogen and a major metabolite of estrone and estradiol.^[1]^[2]^[3] It is formed irreversibly from estrone in the liver and to a lesser extent in other tissues via 2-hydroxylation mediated by cytochrome P450 enzymes, mainly the CYP3A and CYP1A subfamilies.^[1]^[3] 2-OHE1 is the most abundant catechol estrogen in the body.^[3] It is not significantly uterotrophic in bioassays, whereas other hydroxylated estrogen metabolites including 2-hydroxyestradiol, 16α-hydroxyestrone, estriol (16α-hydroxyestradiol), 4-hydroxyestradiol, and 4-hydroxyestrone all are.^[1]^[4]

References

^ ^a ^b ^c Oettel, Michael; Schillinger, Ekkehard (6 December 2012). Estrogens and Antiestrogens I: Physiology and Mechanisms of Action of Estrogens and Antiestrogens. Springer Science & Business Media. p. 227. ISBN 978-3-642-58616-3. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
^ Rakel, David (2012). Integrative Medicine. Elsevier Health Sciences. pp. 338–. ISBN 1-4377-1793-4. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
^ ^a ^b ^c Buchsbaum HJ (6 December 2012). The Menopause. Springer Science & Business Media. pp. 64–65. ISBN 978-1-4612-5525-3.
^ Bhavnani BR, Nisker JA, Martin J, Aletebi F, Watson L, Milne JK (2000). "Comparison of pharmacokinetics of a conjugated equine estrogen preparation (premarin) and a synthetic mixture of estrogens (C.E.S.) in postmenopausal women". Journal of the Society for Gynecologic Investigation. 7 (3): 175–83. PMID 10865186.

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