15α-Hydroxy-DHEA sulfate

15α-Hydroxydehydroepiandrosterone sulfate, abbreviated as 15α-hydroxy-DHEA sulfate or 15α-OH-DHEA-S, also known as 15α-hydroxy-17-oxoandrost-5-en-3β-yl sulfate, is an endogenous, naturally occurring steroid and a metabolic intermediate in the production of estetrol from dehydroepiandrosterone (DHEA) during pregnancy.[1][2][3] It is the C3β sulfate ester of 15α-hydroxy-DHEA.[1][2][3]

15α-Hydroxy-DHEA sulfate

Names
IUPAC name [(3S,8R,9S,10R,13S,14S,15R)-15-Hydroxy-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate
Other names 3β,15α-Dihydroxyandrost-5-en-17-one 3β-sulfate; 15α-Hydroxydehydroepiandrosterone sulfate; 15α-Hydroxy-DHEA sulfate; 15α-OH-DHEA-S
Identifiers
3D model (JSmol)	Interactive image
InChI InChI=1S/C19H28O6S/c1-18-7-5-12(25-26(22,23)24)9-11(18)3-4-13-14(18)6-8-19(2)16(21)10-15(20)17(13)19/h3,12-15,17,20H,4-10H2,1-2H3,(H,22,23,24)/t12-,13+,14-,15-,17+,18-,19+/m0/s1 Key: BORVGNZEVLBZIP-CRYRVXFVSA-N
SMILES C[C@]12CC[C@H]3[C@@H](CC=C4C[C@H](CC[C@]34C)OS(O)(=O)=O)[C@@H]1[C@@H](O)CC2=O
Properties
Chemical formula	C19H28O6S
Molar mass	384.49 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

• Pregnenolone sulfate
• Dehydroepiandrosterone sulfate
• 16α-Hydroxydehydroepiandrosterone
• 16α-Hydroxyandrostenedione
• 16α-Hydroxyestrone
• Estrone sulfate
• C₁₉H₂₈O₆S

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.