Zymostenol

Zymostenol
Names
	IUPAC name (3S,5S,10S,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
	Other names (5α)-cholest-8-en-3β-ol
Identifiers
CAS Number	566-97-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16608 ;
ChemSpider	566-97-2 ;
KEGG	C03845 ;
PubChem CID	101770;
UNII	L3GY707BLC ;
CompTox Dashboard (EPA)	DTXSID30205162;
	InChI InChI=1S/C27H46O/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/h18-21,23-24,28H,6-17H2,1-5H3/t19-,20+,21+,23-,24+,26+,27-/m1/s1 Key: QETLKNDKQOXZRP-XTGBIJOFSA-N ;
	SMILES C[C@H](CCCC(C)C)[C@@]1([H])CC[C@@]([C@]1(C)CC2)([H])C3=C2[C@]4(C)[C@](CC3)([H])C[C@@H](O)CC4;
Properties
Chemical formula	C27H46O
Molar mass	386.664 g·mol−1
Appearance	crystalline solid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). (what is ?) Infobox references

Zymostenol is an intermediate compound in the biosynthesis of cholesterol and other sterols. It is formed during the conversion of lanosterol to cholesterol, a critical metabolic pathway in animals, fungi, and some protozoa.^[1]

Biosynthesis

Zymostenol is produced from 14-demethyl lanosterol via the action of sterol Δ8,7-sterol isomerase (emopamil binding protein, EBP). This step is part of the Bloch pathway of cholesterol biosynthesis, where zymostenol is further converted to zymosterol and then to 7-dehydrocholesterol, a direct precursor to cholesterol.^[2]^[3]^[4]^[5]

References

^ Kautsky, Marie P.; Kautsky, Marie B. (1 July 1981). Steroid Analysis by HPLC: Recent Applications. CRC Press. p. 255. ISBN 978-0-8247-1324-9. Retrieved 23 July 2025.
^ "Zymostenol powder Avanti Polar Lipids". Sigma Aldrich. Retrieved 23 July 2025.
^ Hu, Xiao; Wang, Yahong; Hao, Ling-Yang; Liu, Xikui; Lesch, Chuck A.; Sanchez, Brian M.; Wendling, Jay M.; Morgan, Rodney W.; Aicher, Tom D.; Carter, Laura L.; Toogood, Peter L.; Glick, Gary D. (February 2015). "Sterol metabolism controls TH17 differentiation by generating endogenous RORγ agonists". Nature Chemical Biology. 11 (2): 141–147. doi:10.1038/nchembio.1714. ISSN 1552-4469. PMID 25558972. Retrieved 23 July 2025.
^ Rozman, Damjana; Gebhardt, Rolf (10 August 2020). Mammalian Sterols: Novel Biological Roles of Cholesterol Synthesis Intermediates, Oxysterols and Bile Acids. Springer Nature. p. 12. ISBN 978-3-030-39684-8. Retrieved 23 July 2025.
^ Ridgway, Neale; McLeod, Roger (24 July 2015). Biochemistry of Lipids, Lipoproteins and Membranes. Elsevier. p. 349. ISBN 978-0-444-63449-8. Retrieved 23 July 2025.

[1] Kautsky, Marie P.; Kautsky, Marie B. (1 July 1981). Steroid Analysis by HPLC: Recent Applications. CRC Press. p. 255. ISBN 978-0-8247-1324-9. Retrieved 23 July 2025.

[2] "Zymostenol powder Avanti Polar Lipids". Sigma Aldrich. Retrieved 23 July 2025.

[3] Hu, Xiao; Wang, Yahong; Hao, Ling-Yang; Liu, Xikui; Lesch, Chuck A.; Sanchez, Brian M.; Wendling, Jay M.; Morgan, Rodney W.; Aicher, Tom D.; Carter, Laura L.; Toogood, Peter L.; Glick, Gary D. (February 2015). "Sterol metabolism controls TH17 differentiation by generating endogenous RORγ agonists". Nature Chemical Biology. 11 (2): 141–147. doi:10.1038/nchembio.1714. ISSN 1552-4469. PMID 25558972. Retrieved 23 July 2025.

[4] Rozman, Damjana; Gebhardt, Rolf (10 August 2020). Mammalian Sterols: Novel Biological Roles of Cholesterol Synthesis Intermediates, Oxysterols and Bile Acids. Springer Nature. p. 12. ISBN 978-3-030-39684-8. Retrieved 23 July 2025.

[5] Ridgway, Neale; McLeod, Roger (24 July 2015). Biochemistry of Lipids, Lipoproteins and Membranes. Elsevier. p. 349. ISBN 978-0-444-63449-8. Retrieved 23 July 2025.

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