Chemistry:16α-Hydroxy-DHEA

16α-Hydroxy-DHEA
Names
	IUPAC name 3β,16α-Dihydroxyandrost-5-en-17-one
	Systematic IUPAC name (2R,3aS,3bR,7S,9aR,9bS,11aS)-3,7-Dihydroxy-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-1-one
Identifiers
CAS Number	1232-73-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:27771 ;
ChemSpider	92168 ;
PubChem CID	102030;
UNII	WU2DU6GA72 ;
	InChI InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-16,20-21H,4-10H2,1-2H3/t12-,13+,14-,15-,16+,18-,19-/m0/s1 Key: QQIVKFZWLZJXJT-DNKQKWOHSA-N ; InChI=1/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-16,20-21H,4-10H2,1-2H3/t12-,13+,14-,15-,16+,18-,19-/m0/s1 Key: QQIVKFZWLZJXJT-DNKQKWOHBQ;
	SMILES O=C3[C@]2(CC[C@@H]1[C@@]4(C(=C/C[C@H]1[C@@H]2C[C@H]3O)\C[C@@H](O)CC4)C)C;
Properties
Chemical formula	C19H28O3
Molar mass	304.42 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

16α-Hydroxydehydroepiandrosterone (16α-hydroxy-DHEA or 16α-OH-DHEA) is an endogenous metabolite of dehydroepiandrosterone (DHEA). Both 16α-OH-DHEA and its 3β-sulfate ester, 16α-OH-DHEA-S, are intermediates in the biosynthesis of estriol from dehydroepiandrosterone (DHEA).^[1] 16α-OH-DHEA has estrogenic activity.^[2]

References

↑ "Estriol-3-sulfate in human breast cyst fluid. Concentrations, possible origin, and physiologic implications". Ann. N. Y. Acad. Sci. 586: 83–7. 1990. doi:10.1111/j.1749-6632.1990.tb17793.x. PMID 2141460.
↑ "DHEA metabolites activate estrogen receptors alpha and beta". Steroids 78 (1): 15–25. 2013. doi:10.1016/j.steroids.2012.10.002. PMID 23123738.

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