Dammarane

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Dammarane
Dammarane.svg
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
PubChem CID
  • 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 X mark.svgN
    Key: OORMXZNMRWBSTK-LGFJJATJSA-N X mark.svgN
  • 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

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Dammar, also called dammar gum, or damar gum, is a resin obtained from the tree family Dipterocarpaceae in India and Southeast Asia, principally those of the genera Shorea or Hopea. The resin of some species of Canarium may also called dammar. Most is produced by tapping trees; however, some is collected in fossilised form on the ground. The gum varies in colour from clear to pale yellow, while the fossilised form is grey-brown. Dammar gum is a triterpenoid resin, containing many triterpenes and their oxidation products. Many of them are low molecular weight compounds, but dammar also contains a polymeric fraction, composed of polycadinene. The name dammar is a Malay word meaning ‘resin’ or ‘torch made from resin’.

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30
H
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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