Lanostane
Encyclopedia
Lanostane or 4,4,14-trimethylcholestane is a chemical compound
with formula . It is a polycyclic hydrocarbon, specifically a triterpene
. It is an isomer of cucurbitane
.
The name is applied to two stereoisomers, distinguished by the prefixes 5α- and 5β-, which differ by the handedness of the bonds at a particular carbon
atom (number 5 in the standard steroid numbering scheme).
Replacement of a hydrogen
atom attached to carbon
number 3 in the 5α isomer with a hydroxyl group results in lanosterol
, the biogenetic
precursor of the steroid
s in animals.
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...
with formula . It is a polycyclic hydrocarbon, specifically a triterpene
Triterpene
Triterpenes are terpenes consisting of six isoprene units and have the molecular formula C30H48.The pentacyclic triterpenes can be classified into lupane, oleanane or ursane groups.Animal- and plant-derived triterpenes exist, such as:*squalene...
. It is an isomer of cucurbitane
Cucurbitane
Cucurbitane is a chemical compound with formula . It is a polycyclic hydrocarbon, specifically a triterpene. It is an isomer of lanostane , from which it differs by the formal shift of a methyl group from the 10 to the 9β position in the standard steroid numbering scheme.The name is applied to...
.
The name is applied to two stereoisomers, distinguished by the prefixes 5α- and 5β-, which differ by the handedness of the bonds at a particular carbon
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...
atom (number 5 in the standard steroid numbering scheme).
Replacement of a hydrogen
Hydrogen
Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...
atom attached to carbon
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...
number 3 in the 5α isomer with a hydroxyl group results in lanosterol
Lanosterol
Lanosterol is a tetracyclic triterpenoid, which is the compound from which all steroids are derived.-Role in creation of steroids:Elaboration of lanosterol under enzyme catalysis leads to the core structure of steroids. 14-Demethylation of lanosterol by CYP51 eventually yields...
, the biogenetic
Biogenesis
Biogenesis is the law that living things come only from other living things, e.g. a spider lays eggs, which develop into spiders. It may also refer to biochemical processes of production in living organisms.-Spontaneous generation:...
precursor of the steroid
Steroid
A steroid is a type of organic compound that contains a characteristic arrangement of four cycloalkane rings that are joined to each other. Examples of steroids include the dietary fat cholesterol, the sex hormones estradiol and testosterone, and the anti-inflammatory drug dexamethasone.The core...
s in animals.