Malabaricane

Chemical compound From Wikipedia, the free encyclopedia

The molecule malabaricane and its derivatives, the malabaricanes, are triterpene and triterpenoid compounds found in various organisms.[1] They are named after the rain forest tree Ailanthus malabarica (Ailanthus triphysa), from which they were first isolated in 1967 by scientists at the National Chemical Laboratory in Pune, India.[2] Later, great varieties of malabaricanes were discovered in other organisms, mostly in marine sponges such as Rhabdastrella globostellata.[3][4]

Quick facts Names, Identifiers ...
Malabaricane
Names
IUPAC name
(3S,3aS,5aS,9aS,9bS)-Dodecahydro-3a,6,6,9a-tetramethyl-3-[(5R)-1,5,9-trimethyldecyl]-1H-benz[e]indene
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C30H56/c1-22(2)12-9-13-23(3)14-10-15-24(4)25-16-17-27-29(25,7)21-18-26-28(5,6)19-11-20-30(26,27)8/h22-27H,9-21H2,1-8H3/t23-,24+,25+,26-,27+,29+,30+/m1/s1
    Key: SGHXJVFMQPUFPZ-LKPKTCMESA-N
  • C[C@@H](CCC[C@H](C)[C@@H]1CC[C@H]2[C@]1(CC[C@H]3[C@@]2(CCCC3(C)C)C)C)CCCC(C)C
Properties
C30H56
Molar mass 416.778 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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Isomalabaricanes are malabaricanes in which the three carbon rings of the molecule are connected in trans−syn−trans conformation, as opposed to other malabaricanes, where the rings are connected in trans−anti−trans conformation. They are of particular research interest because many of them have been reported to show anti-tumour activity in cell culture.[5][6]

References

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