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| Names | |
|---|---|
| IUPAC name 5ξ-Gonane | |
| Systematic IUPAC name (3aR,3bS,5aΞ,9aS,9bR,11aS)-Hexadecahydro-1H-cyclopenta[a]phenanthrene | |
| Identifiers | |
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3D model (JSmol) | |
| ChEBI | |
| ChemSpider | |
| KEGG |
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| Properties | |
| C17H28 | |
| Molar mass | 232.411 g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Gonane (cyclopentanoperhydrophenanthrene) is a chemical compound with formulaC
17H
28, whose structure consists of fourhydrocarbon ringsfused together: threecyclohexane units and onecyclopentane. It can also be viewed as the result of fusing a cyclopentane molecule with a fullyhydrogenated molecule ofphenanthrene, hence the more descriptive name "perhydrocyclopenta[a]phenanthrene". The non-systematic version of the above name is "cyclopentanoperhydrophenanthrene".[1]
It has no double bonds, that is, it is completelysaturated and is considered the main structure ofsteroids, often referred to as thesteroid nucleus.[1] There are many forms of gonane, but only a few occur naturally in living organisms. Some common forms include 5α-gonane and 5β-gonane.Estrane,androstane, andpregnane are derivatives of gonane with additional methyl or ethyl groups attached to certain carbon positions. The term gonane is also used to describe a group ofprogestins that are similar tolevonorgestrel but have a slightly different structure than other hormones like estranes.
Gonane is a significant chemical compound in the family ofsteroids because its structure comprises four hydrocarbon rings fused together, consisting of three cyclohexane units and one cyclopentane, which is often referred to as the "steroid nucleus" and serves as the parent compound for steroids.
The discovery of gonane and its role as a steroid nucleus has been fundamental in understanding the structure and function of varioussteroid hormones. The numbering of steroid rings is determined based on the skeletal structure of gonane, providing a framework for the classification and identification of different steroids.
The term gonane is also used to refer to a group ofprogestins[2] that are carbon 18-homologated 19-nortestosterone derivatives includinglevonorgestrel and itsanalogues.[3] This term is used in this way in order to distinguish them fromestranes, which are also 19-nortestosterone derivatives.[3]
Gonane is atetracyclichydrocarbon with no double bonds. It is formally the parent compound of thesteroids, hence it is called the "steroid nucleus".[1][4][5] Some important gonane derivatives are thesteroid hormones, characterized bymethyl groups at the C10 and C13 positions and aside chain at the C17 position.[5]
Because gonane has sixcenters of chirality, it has 64 (26) theoretically possiblestereoisomers,[4] that differ on the position of the lone hydrogens at carbons 5, 8, 9, 10, 13 and 14 in the direction perpendicular to the mean plane of the carbons. However, only a few of these stereoisomers occur in living organisms.[4] The most common are5α-gonane and5β-gonane.
Estrane (C18) is the 13β-methyl variant of gonane,androstane (C19) is the 10β,13β-dimethyl variant of gonane, andpregnane (C21) is the 10β,13β-dimethyl, 17β-ethyl variant of gonane.[6][7]
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