Gonane
Tetracyclic hydrocarbon parent of the steroids / From Wikipedia, the free encyclopedia
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Gonane (cyclopentanoperhydrophenanthrene) is a chemical compound with formula C
17H
28, whose structure consists of four hydrocarbon rings fused together: three cyclohexane units and one cyclopentane. It can also be viewed as the result of fusing a cyclopentane molecule with a fully hydrogenated molecule of phenanthrene, hence the more descriptive name "perhydrocyclopenta[a]phenanthrene". The non-systematic version of the above name is "cyclopentanoperhydrophenanthrene".[1]
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IUPAC name
5ξ-Gonane | |
Systematic IUPAC name
(3aR,3bS,5aΞ,9aS,9bR,11aS)-Hexadecahydro-1H-cyclopenta[a]phenanthrene | |
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Properties | |
C17H28 | |
Molar mass | 232.411 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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It has no double bonds, that is, it is completely saturated and is considered the main structure of steroids, often referred to as the steroid 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, and pregnane are variants of gonane with additional methyl or ethyl groups attached to certain carbon positions. The term gonane is also used to describe a group of progestins that are similar to levonorgestrel but have a slightly different structure than other hormones like estranes.