Tirucallane

Tirucallane
Names
	IUPAC name (20S)-13α,14β,17α-Lanostane
	Systematic IUPAC name (1S,3aR,3bR,5aS,9aR,9bS,11aS)-3a,6,6,9a,11a-Pentamethyl-1-[(2S)-6-methylheptan-2-yl]hexadecahydro-1H-cyclopenta[a]phenanthrene
	Other names (13α,14β,17α,20S)-Lanostane
Identifiers
CAS Number	2151853-72-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:73301;
ChemSpider	21376191;
PubChem CID	12312922;
UNII	CWP59NF9TF ;
CompTox Dashboard (EPA)	DTXSID501310798 ;
	InChI InChI=1S/C30H54/c1-21(2)11-9-12-22(3)23-15-19-30(8)25-13-14-26-27(4,5)17-10-18-28(26,6)24(25)16-20-29(23,30)7/h21-26H,9-20H2,1-8H3/t22-,23-,24-,25+,26-,28+,29-,30+/m0/s1 Key: ZQIOPEXWVBIZAV-RSKDDJKESA-N;
	SMILES C[C@@H](CCCC(C)C)[C@@H]1CC[C@]2([C@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CCCC4(C)C)C)C)C;
Properties
Chemical formula	C30H54
Molar mass	414.762 g·mol−1
Density	0.897±0.06 g·cm−3
Boiling point	461.3±12.0 °C
Solubility in water	hard in water
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tirucallane is a tetracyclic triterpene with the chemical formula C₃₀H₅₄. It is the 20S-stereoisomer of euphane and its derivatives, such as tirucalladienol,^[2] are found in Euphorbia^[3] and other plants.^[4]

References

1 2 3 Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (© 1994-2019 ACD/Labs). Retrieved from SciFinder. [2019-10-19]
↑ Arigoni D, Wyler H, Jeger O (1954). "Zur Kenntnis der Triterpene. 179. Mitteilung. Über die gegenseitigen Beziehungen bei Elemadienolsäure, Tirucalladienol und Euphorbadienol". Helvetica Chimica Acta. 37 (5): 1553–1558. doi:10.1002/hlca.19540370524.
↑ Wang LY, Wang NL, Yao XS, Miyata S, Kitanaka S (2003). "Euphane and tirucallane triterpenes from the roots of Euphorbia kansui and their in vitro effects on the cell division of Xenopus". J Nat Prod. 66 (5): 660–663. doi:10.1021/np0205396. PMID 12762796.
↑ Xu J, Xiao D, Lin QH, He JF, Liu WY, Xie N, Feng F, Qu W (2016). "Cytotoxic Tirucallane and Apotirucallane Triterpenoids from the Stems of Picrasma quassioides". J Nat Prod. 79 (8): 1899–1910. doi:10.1021/acs.jnatprod.5b01137. PMID 27494664.