Lupane (compound)
Organic compound (C30H50); pentacyclic triterpene hydrocarbon
From Wikipedia, the free encyclopedia
Lupane is a pentacyclic triterpene hydrocarbon with the molecular formula C30H52. It serves as the core skeleton for various bioactive compounds, including lupeol and betulinic acid, which are prevalent in numerous plant species.[1] It actually features a structure composed of five fused rings––four cyclohexane rings and one cyclopentane––and is one of the major triterpene skeletons alongside hopane, oleanane, and ursane types. The compound is common in birch bark.
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| Names | |
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| IUPAC name
(1S,3aR,5aR,5bR,7aS,11aS,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-Hexamethyl-1-propan-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene | |
| Identifiers | |
3D model (JSmol) |
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| 2562721 | |
| ChEBI | |
| ChemSpider | |
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C30H52 | |
| Molar mass | 412.746 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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Occurrence and derivatives
Derivatives of lupane, such as lupeol, betulin, and betulinic acid, are found in high concentrations in birch bark (Betula spp.), mango peels, olives, strawberries, and other fruits.[2]
Similar derivatives
Similar derivatives are the following ones:
- Lupeol (C30H50O) – a hydroxylated lupane at position C‑3, with noted anti-inflammatory and anti‑cancer effects.
- Betulin (C30H50O2) – a diol lupane naturally abundant in birch bark (up to 30% by dry weight) and researched for wound healing and pharmaceutical uses.[citation needed]
- Betulinic acid – the oxidized carboxylic acid form of betulin; one of the most extensively studied lupane-derived compounds with anticancer activity.[3]