Cholesterol sulfate

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Cholesterol sulfate
Cholesterol sulfate.svg
Names
IUPAC name
[(3S,8S,9S,10R,13R,14S,17R)-10,13-Dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate
Other names
Cholest-5-en-3β-ol sulfate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • 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/s1
    Key: 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/s1
    Key: BHYOQNUELFTYRT-DPAQBDIFBL
  • C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)OS(=O)(=O)O)C)C
Properties
C27H46O4S
Molar mass 466.72 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cholesterol sulfate, or cholest-5-en-3β-ol sulfate, is an endogenous steroid and the C3β sulfate ester of cholesterol.[1][2] It is formed from cholesterol by steroid sulfotransferases (SSTs) such as SULT2B1b (also known as cholesterol sulfotransferase)[2] and is converted back into cholesterol by steroid sulfatase (STS).[1] 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.[1][2]

See also[edit]

References[edit]

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