Zymosterol

Last updated
Zymosterol
Zymosterol.png
Zymosterol molecule ball.png
Names
IUPAC name
5α-Cholesta-8,24-dien-3β-ol
Systematic IUPAC name
(1R,3aR,5aS,7S,9aS,11aR)-9a,11a-Dimethyl-1-[(2R)-6-methylhept-5-en-2-yl]-2,3,3a,4,5,5a,6,7,8,9,9a,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-ol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.438 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,19-21,23-24,28H,6,8-17H2,1-5H3/t19-,20+,21+,23-,24+,26+,27-/m1/s1 X mark.svgN
    Key: CGSJXLIKVBJVRY-XTGBIJOFSA-N X mark.svgN
  • InChI=1/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,19-21,23-24,28H,6,8-17H2,1-5H3/t19-,20+,21+,23-,24+,26+,27-/m1/s1
    Key: CGSJXLIKVBJVRY-XTGBIJOFBJ
  • O[C@H]4CC[C@@]3(/C2=C(/[C@@H]1CC[C@H]([C@H](C)CC\C=C(/C)C)[C@@]1(C)CC2)CC[C@H]3C4)C
Properties
C27H4O
Molar mass 344.328 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Zymosterol is an intermediate in cholesterol biosynthesis. [1] Disregarding some intermediate compounds (e.g. 4-4-dimethylzymosterol), lanosterol can be considered a precursor of zymosterol in the cholesterol synthesis pathway. The conversion of zymosterol into cholesterol happens in the endoplasmic reticulum. Zymosterol accumulates quickly in the plasma membrane coming from the cytosol. The movement of zymosterol across the cytosol is more than twice as fast as the movement of cholesterol itself.

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References

  1. Dolle, Roland E.; Schmidt, Stanley J.; Erhard, Karl F.; Kruse, Lawrence I. (1989). "Synthesis of zymosterol, fecosterol, and related biosynthetic sterol intermediates". Journal of the American Chemical Society. 111 (1): 278–284. Bibcode:1989JAChS.111..278D. doi:10.1021/ja00183a042.