Sterol

Sterol

Names
IUPAC name 2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17-hexadecahydro-1H-cyclopenta[a]phenanthren-3-ol
Other names Hexadecahydro-3H-cyclopenta[a]phenanthrene-3-ol
Identifiers
3D model (JSmol)	Interactive image Gonan-3-ol: Interactive image
ChEBI	CHEBI:36834 Gonan-3-ol: CHEBI:177508
ChemSpider	1076
KEGG	C00370
PubChem CID	1107
InChI InChI=1S/C17H28O/c18-13-6-9-15-12(10-13)5-8-16-14-3-1-2-11(14)4-7-17(15)16/h11-18H,1-10H2 Key: FPXSXMFOYWRHDX-UHFFFAOYSA-N Gonan-3-ol: InChI=1S/C17H28O/c18-13-6-9-15-12(10-13)5-8-16-14-3-1-2-11(14)4-7-17(15)16/h11-18H,1-10H2/t11-,12?,13?,14+,15-,16-,17+/m0/s1 Key: FPXSXMFOYWRHDX-BBLQPCNESA-N
SMILES C1CC2CCC3C4CCC(CC4CCC3C2C1)O Gonan-3-ol: OC1CC2[C@@]([C@@]3([C@]([C@]4([C@](CC3)(CCC4)[H])[H])(CC2)[H])[H])(CC1)[H]
Properties
Chemical formula	C17H28O
Molar mass	248.410 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Sterol is an organic compound^[1] with formula C
₁₇H
₂₈O, whose molecule is derived from that of gonane by replacement of a hydrogen atom on C3 position by a hydroxyl group. It is therefore an alcohol of gonane. More generally, any compounds that contain the gonane structure, additional functional groups, and/or modified ring systems derived from gonane are called steroids. Therefore, sterols are a subgroup of the steroids. They occur naturally in most eukaryotes, including plants, animals, and fungi, and can also be produced by some bacteria (however likely with different functions). ^[2][3] The most familiar type of animal sterol is cholesterol, which is vital to the structure of the cell membrane, and functions as a precursor to fat-soluble vitamins and steroid hormones.

While technically alcohols, sterols are classified by biochemists as lipids (fats in the broader sense of the term).