Zymosterol - Misplaced Pages

Zymosterol
Names


IUPAC name 5α-Cholesta-8,24-dien-3β-ol
Systematic IUPAC name (1R,3aR,5aS,7S,9aS,11aR)-9a,11a-Dimethyl-1--2,3,3a,4,5,5a,6,7,8,9,9a,10,11,11a-tetradecahydro-1H-cyclopentaphenanthren-7-ol
Identifiers
CAS Number	128-33-6
3D model (JSmol)	Interactive image
ChemSpider	83724
ECHA InfoCard	100.004.438
PubChem CID	92746
UNII	PU2755PT4O
CompTox Dashboard (EPA)	DTXSID201028211
InChI 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/s1Key: CGSJXLIKVBJVRY-XTGBIJOFSA-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/s1Key: CGSJXLIKVBJVRY-XTGBIJOFBJ
SMILES O4CC3(/C2=C(/1CC((C)CC\C=C(/C)C)1(C)CC2)CC3C4)C
Properties
Chemical formula	C₂₇H₄O
Molar mass	344.328 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

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.

References

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.

Cholesterol and steroid metabolic intermediates

Mevalonate pathway

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

Non-mevalonate pathway

To Cholesterol

From Cholesterol
to Steroid hormones

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

This article about a steroid is a stub. You can help Misplaced Pages by expanding it.

Categories: