Dammarane

Dammarane
Names
IUPAC name
Dammarane[1]
Systematic IUPAC name
(1R,3aR,3bR,5aS,9aS,9bR,11aR)-1-[(2R)-6-Methylheptan-2-yl]-3a,3b,6,6,9a-pentamethylhexadecahydro-1H-cyclopenta[a]phenanthrene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
MeSH C102963
  • InChI=1S/C30H54/c1-21(2)11-9-12-22(3)23-15-19-29(7)24(23)13-14-26-28(6)18-10-17-27(4,5)25(28)16-20-30(26,29)8/h21-26H,9-20H2,1-8H3/t22-,23-,24-,25+,26-,28+,29-,30-/m1/s1 ☒N
    Key: OORMXZNMRWBSTK-LGFJJATJSA-N ☒N
  • InChI=1/C30H54/c1-21(2)11-9-12-22(3)23-15-19-29(7)24(23)13-14-26-28(6)18-10-17-27(4,5)25(28)16-20-30(26,29)8/h21-26H,9-20H2,1-8H3/t22-,23-,24-,25+,26-,28+,29-,30-/m1/s1
    Key: OORMXZNMRWBSTK-LGFJJATJBV
  • C[C@H](CCCC(C)C)[C@H]1CC[C@@]2([C@@H]1CC[C@H]3[C@]2(CC[C@@H]4[C@@]3(CCCC4(C)C)C)C)C
Properties
C30H54
Molar mass 414.75 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dammarane is a tetracyclic triterpene found in sapogenins (forming triterpenoid saponins) like those of ginseng (ginsenosides: panaxatriol and protopanaxadiol). Compounds of the series were first isolated from and named after dammar resin, a natural resin from the tropical trees of the dipterocarp family.[2] [3]

References

  1. ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1535. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. ^ Mills J.S.; Werner A.E.A. (1955). "The Chemistry of Dammar Resin". Journal of the Chemical Society: 3132–40. doi:10.1039/jr9550003132.
  3. ^ Mills J.S. (1956) "The Constitution of the Neutral, Tetracyclic Triterpenes of Dammar Resin" Journal of the Chemical Society 2196-2202


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