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7α-Hydroxycholesterol

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7α-Hydroxycholesterol
Names
IUPAC name
(3S,7S,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]phenanthrene-3,7-diol
Identifiers
3D model (JSmol)
ChemSpider
MeSH 7+alpha-hydroxycholesterol
UNII
  • InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24-,25+,26+,27-/m1/s1 checkY
    Key: OYXZMSRRJOYLLO-RVOWOUOISA-N checkY
  • InChI=1/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24-,25+,26+,27-/m1/s1
    Key: OYXZMSRRJOYLLO-RVOWOUOIBF
  • CC(C)CCC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](C=C4[C@@]3(CC[C@@H](C4)O)C)O)C
  • O[C@@H]4C/C3=C/[C@@H](O)[C@@H]1[C@H](CC[C@]2([C@H]1CC[C@@H]2[C@H](C)CCCC(C)C)C)[C@@]3(C)CC4
Properties
C27H46O2
Molar mass 402.653 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

7α-Hydroxycholesterol is a precursor of bile acids, created by cholesterol 7α-hydroxylase. Its formation is the rate-determining step in bile acid synthesis.[1]

References

  1. ^ Miao, Ji (2008). Regulation of Bile Acid Biosynthesis by Orphan Nuclear Receptor Small Heterodimer Partner (Ph.D.). University of Illinois at Urbana-Champaign. {{cite thesis}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)