Lupane (compound)

Lupane

Names
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
CAS Number	464-99-3
3D model (JSmol)	Interactive image
Beilstein Reference	2562721
ChEBI	CHEBI:36485
ChemSpider	2340755
PubChem CID	9548715
CompTox Dashboard (EPA)	DTXSID40963569
InChI InChI=1S/C30H52/c1-20(2)21-12-16-27(5)18-19-29(7)22(25(21)27)10-11-24-28(6)15-9-14-26(3,4)23(28)13-17-30(24,29)8/h20-25H,9-19H2,1-8H3/t21-,22+,23-,24+,25+,27+,28-,29+,30+/m0/s1 Key: NKMDIWKRKQFYPH-VIUFNMEASA-N
SMILES CC(C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CCCC([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)C)C
Properties
Chemical formula	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). Infobox references

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. 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.

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.

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.
• Betulinic acid – the oxidized carboxylic acid form of betulin; one of the most extensively studied lupane-derived compounds with anticancer activity.