15α-Hydroxy-DHEA

15α-Hydroxydehydroepiandrosterone, abbreviated as 15α-hydroxy-DHEA or 15α-OH-DHEA, is an endogenous metabolite of dehydroepiandrosterone (DHEA).[1][2][3] Both 15α-OH-DHEA and its 3β-sulfate ester, 15α-OH-DHEA-S, are intermediates in the biosynthesis of estetrol from dehydroepiandrosterone (DHEA).[1][2][3]

15α-Hydroxy-DHEA
Names
IUPAC name
3β,15α-Dihydroxyandrost-5-en-17-one
Systematic IUPAC name
(3S,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
Other names
15α-Hydroxydehydroepiandrosterone; 15α-Hydroxy-DHEA; 15α-OH-DHEA
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)16(22)10-15(21)17(13)19/h3,12-15,17,20-21H,4-10H2,1-2H3/t12-,13+,14-,15-,17+,18-,19+/m0/s1
    Key: SWXQUEHVFFSZOW-CRYRVXFVSA-N
  • InChI=1/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)16(22)10-15(21)17(13)19/h3,12-15,17,20-21H,4-10H2,1-2H3/t12-,13+,14-,15-,17+,18-,19+/m0/s1
    Key: SWXQUEHVFFSZOW-CRYRVXFVBS
  • C[C@]12CC[C@@H](CC1=CC[C@@H]3[C@@H]2CC[C@]4([C@H]3[C@H](CC4=O)O)C)O
Properties
C19H28O3
Molar mass 304.430 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. Roger Smith (Prof.) (1 January 2001). The Endocrinology of Parturition: Basic Science and Clinical Application. Karger Medical and Scientific Publishers. pp. 91–. ISBN 978-3-8055-7195-1.
  2. J.B. Josimovich (11 November 2013). Gynecologic Endocrinology. Springer Science & Business Media. pp. 32–. ISBN 978-1-4613-2157-6.
  3. Jerome F. Strauss, III; Robert L. Barbieri (13 September 2013). Yen and Jaffe's Reproductive Endocrinology. Elsevier Health Sciences. pp. 257–. ISBN 978-1-4557-2758-2.



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