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Zymosterol

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Zymosterol
Ball-and-stick model of zymosterol
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

CAS Number

3D model (JSmol)

ChemSpider
ECHA InfoCard 100.004.438 Edit this at Wikidata

PubChem CID

UNII

CompTox Dashboard (EPA)

  • 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 ☒N

    Key: CGSJXLIKVBJVRY-XTGBIJOFSA-N ☒N

  • 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

Chemical formula

C27H44O
Molar mass 384.64 g/mol

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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Infobox references

Zymosterol is an intermediate in cholesterol biosynthesis. 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.