Cholane is a
triterpene
Triterpenes are a class of chemical compounds composed of three terpene units with the molecular formula C30H48; they may also be thought of as consisting of six isoprene units. Animals, plants and fungi all produce triterpenes, including squale ...
which can exist as either of two
stereoisomer
In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in ...
s, 5α-cholane and 5β-cholane. Its name is derived from el, χολή (chole) meaning 'bile' in reference to its original discovery from the bile of the
American bullfrog
The American bullfrog (''Lithobates catesbeianus''), often simply known as the bullfrog in Canada and the United States, is a large true frog native to eastern North America. It typically inhabits large permanent water bodies such as swamps, po ...
(''Rana catesbeiana'').
The compound itself has no known uses. However, various functionalized analogues are produced by plants and animals, typically in the form of
sterol
Sterol is an organic compound with formula , whose molecule is derived from that of gonane by replacement of a hydrogen atom in position 3 by a hydroxyl group. It is therefore an alcohol of gonane. More generally, any compounds that contain the go ...
s,
steroid
A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and a ...
s and
bile acids
Bile acids are steroid acids found predominantly in the bile of mammals and other vertebrates. Diverse bile acids are synthesized in the liver. Bile acids are conjugated with taurine or glycine residues to give anions called bile salts.
Primary b ...
(e.g.
cholic acid
Cholic acid, also known as 3α,7α,12α-trihydroxy-5β-cholan-24-oic acid is a primary bile acid that is insoluble in water (soluble in alcohol and acetic acid), it is a white crystalline substance. Salts of cholic acid are called cholates. Ch ...
).
Image:5alpha-Cholane.svg, 5α-Cholane
Image:5beta-Cholane.svg, 5β-Cholane
See also
*
Cholestane
Cholestane is a saturated tetracyclic triterpene. This 27-carbon biomarker is produced by diagenesis of cholesterol and is one of the most abundant biomarkers in the rock record. Presence of cholestane, its derivatives and related chemical compoun ...
*
Ergostane
Ergostane is a tetracyclic triterpene, also known as 24''S''-methylcholestane. The compound itself has no known uses; however various functionalized analogues are produced by plants and animals. The most important of these are the heavily derivati ...
References
External links
* {{MeshName, Cholanes
Triterpenes
Cholanes
Cyclopentanes