Tirucallane

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Tirucallane
Tirucallane.svg
Names
Preferred 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
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • 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
  • 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
C30H54
Molar mass 414.762 g·mol−1
Density 0.897±0.06 g·cm−3[1]
Boiling point 461.3±12.0 °C[1]
hard in water[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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]

Tirucalladienol

See also[edit]

References[edit]

  1. ^ a b c Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (© 1994-2019 ACD/Labs). Retrieved from SciFinder. [2019-10-19]
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.