Cholesterol sulfate - Misplaced Pages

Cholesterol sulfate
Names

IUPAC name -2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopentaphenanthren-3-yl] hydrogen sulfate
Other names Cholest-5-en-3β-ol sulfate
Identifiers
CAS Number	1256-86-6
3D model (JSmol)	Interactive image
ChEBI	CHEBI:41321
ChEMBL	ChEMBL1231592
ChemSpider	58586
PubChem CID	65076
UNII	KU576NT9O9
InChI InChI=1S/C27H46O4S/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(31-32(28,29)30)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25H,6-8,10-17H2,1-5H3,(H,28,29,30)/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1Key: BHYOQNUELFTYRT-DPAQBDIFSA-N InChI=1/C27H46O4S/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(31-32(28,29)30)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25H,6-8,10-17H2,1-5H3,(H,28,29,30)/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1Key: BHYOQNUELFTYRT-DPAQBDIFBL
SMILES C(CCCC(C)C)1CC21(CC32CC=C43(CC(C4)OS(=O)(=O)O)C)C
Properties
Chemical formula	C₂₇H₄₆O₄S
Molar mass	466.72 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Cholesterol sulfate, or cholest-5-en-3β-ol sulfate, is an endogenous steroid and the C3β sulfate ester of cholesterol. It is formed from cholesterol by steroid sulfotransferases (SSTs) such as SULT2B1b (also known as cholesterol sulfotransferase) and is converted back into cholesterol by steroid sulfatase (STS). Accumulation of cholesterol sulfate in the skin is implicated in the pathophysiology of X-linked ichthyosis, a congenital disorder in which STS is non-functional and the body cannot convert cholesterol sulfate back into cholesterol.

References

^ Peter M. Elias (21 January 2016). Advances in Lipid Research: Skin Lipids. Elsevier. pp. 45–46. ISBN 978-1-4832-1545-7.
^ P. Itin; G. Jemec (15 September 2010). Ichthyoses. Karger Medical and Scientific Publishers. pp. 59–. ISBN 978-3-8055-9395-3.

Others

to HMG-CoA	Acetyl-CoA Acetoacetyl-CoA HMB HMB-CoA HMG-CoA
Ketone bodies	Acetone Acetoacetic acid β-Hydroxybutyric acid
to DMAPP	Mevalonic acid Phosphomevalonic acid 5-Diphosphomevalonic acid Isopentenyl pyrophosphate Dimethylallyl pyrophosphate
Geranyl-	Geranyl pyrophosphate Geranylgeranyl pyrophosphate
Carotenoid	Prephytoene diphosphate Phytoene

Nonhuman

To Sitosterol	Cycloartenol Cycloeucalenol Obtusifoliol 4α-methylfecosterol Isofucosterol 24-Methylenelophenol Sitosterol More Phytosterols see here instead.
To Ergocalciferol	Fecosterol Episterol Ergostatrienol Ergostatetraenol Ergosterol Ergocalciferol

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