Estriol sulfate

Estriol sulfate, or estriol 3-sulfate, is a conjugated metabolite of estriol that is present in high quantities during pregnancy. It is formed from estriol in the liver and is eventually excreted in the urine by the kidneys. It has much higher water solubility than does estriol. Estriol sulfate is the second most prevalent conjugated metabolite of estriol during pregnancy; 35 to 46% is estriol glucuronide and 15 to 22% is estriol 3-sulfate, while the double conjugate estriol sulfate glucuronide also occurs.^[1][2] Estriol sulfate was a component, along with estriol glucuronide, of the early pharmaceutical estrogens Progynon and Emmenin.^[3][4][5][1]

Estriol sulfate

Names
IUPAC name 16α,17β-Dihydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulfate
Systematic IUPAC name (1R,2R,3aS,3bR,9bS,11aS)-1,2-Dihydroxy-11a-methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthren-7-yl hydrogen sulfate
Other names Estriol 3-sulfate; Estra-1,3,5(10)-triene-3,16α,17β-triol 3-sulfate
Identifiers
CAS Number	481-95-8 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL2074797
ChemSpider	59789
PubChem CID	66415
UNII	LZ7JHK6R2A Y
CompTox Dashboard (EPA)	DTXSID50963999
InChI InChI=1S/C18H24O6S/c1-18-7-6-13-12-5-3-11(24-25(21,22)23)8-10(12)2-4-14(13)15(18)9-16(19)17(18)20/h3,5,8,13-17,19-20H,2,4,6-7,9H2,1H3,(H,21,22,23)/t13-,14-,15+,16-,17+,18+/m1/s1 Key: ZORQMBLUMWNJEQ-ZXXIGWHRSA-N
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)O)CCC4=C3C=CC(=C4)OS(=O)(=O)O
Properties
Chemical formula	C18H24O6S
Molar mass	368.44 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

• Catechol estrogen
• Estradiol glucuronide
• Estradiol sulfate
• Estrogen conjugate
• Estrone glucuronide
• Estrone sulfate
• Lipoidal estradiol

References

1. N. S. Assali (3 September 2013). The Maternal Organism. Elsevier. pp. 339–. ISBN 978-1-4832-6380-9.
2. Helmut Sies; Lester Packer (2005). Phase II Conjugation Enzymes and Transport Systems. Gulf Professional Publishing. pp. 294–. ISBN 978-0-12-182805-9.
3. Thom Rooke (1 January 2012). The Quest for Cortisone. MSU Press. pp. 54–. ISBN 978-1-60917-326-5.
4. Gregory Pincus (22 October 2013). Recent Progress in Hormone Research: The Proceedings of the Laurentian Hormone Conference. Elsevier Science. pp. 307–. ISBN 978-1-4832-1945-5.
5. Robert K. Creasy; Robert Resnik; Charles J. Lockwood; Jay D. Iams; Michael F. Greene; Thomas Moore (2013). Creasy and Resnik's Maternal-Fetal Medicine: Principles and Practice. Elsevier Health Sciences. pp. 104–. ISBN 978-1-4557-1137-6.