Labdane

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Labdane
Labdane.svg
Names
IUPAC name
Labdane
Systematic IUPAC name
(4aR,5S,6S,8aS)-1,1,4a,6-Tetramethyl-5-[(3R)-3-methylpentyl]decahydronaphthalene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C20H38/c1-7-15(2)9-11-17-16(3)10-12-18-19(4,5)13-8-14-20(17,18)6/h15-18H,7-14H2,1-6H3/t15-,16+,17+,18+,20-/m1/s1 Yes check.svgY
    Key: LEWJAHURGICVRE-AISVETHESA-N Yes check.svgY
  • InChI=1/C20H38/c1-7-15(2)9-11-17-16(3)10-12-18-19(4,5)13-8-14-20(17,18)6/h15-18H,7-14H2,1-6H3/t15-,16+,17+,18+,20-/m1/s1
    Key: LEWJAHURGICVRE-AISVETHEBV
  • C2CC([C@@H]1CC[C@@H]([C@@H]([C@@]1(C)C2)CC[C@H](C)CC)C)(C)C
Properties
C20H38
Molar mass 278.524 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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Labdane is a natural bicyclic diterpene. It forms the structural core for a wide variety of natural products collectively known as labdanes or labdane diterpenes. The labdanes were so named because the first members of the class were originally obtained from labdanum, a resin derived from the gum rockrose. [1] [2]

Contents

A variety of biological activities have been determined for labdane diterpenes including antibacterial, antifungal, antiprotozoal, and anti-inflammatory activities. [3] Natural labdanes in tree resin are believed to be the precursors of amber, which polymerise under great pressure.

Example labdane derivatives

See also

References

  1. ↑ Cocker, J. D.; Halsall, T. G.; Bowers, A. (1956). "The chemistry of gum labdanum. I. Some acidic constituents". Journal of the Chemical Society: 4259–62. doi:10.1039/jr9560004259.
  2. ↑ Cocker, J. D.; Halsall, T. G. (1956). "The chemistry of gum labdanum. II. The structure of labdanolic acid". Journal of the Chemical Society: 4262–71. doi:10.1039/jr9560004262.
  3. ↑ Atta-Ur-Rahman, ed. (1988). Studies in Natural Product Chemistry : Bioactive Natural Products, Part F. ISBN   978-0-08-044001-9.
  4. ↑ Kenmogne, Marguerite; Prost, Elise; Harakat, Dominique; Jacquier, Marie-José; Frédérich, Michel; Sondengam, Lucas B.; Zèches, Monique; Waffo-Téguo, Pierre (1 March 2006). "Five labdane diterpenoids from the seeds of Aframomum zambesiacum". Phytochemistry. 67 (5): 433–438. Bibcode:2006PChem..67..433K. doi:10.1016/j.phytochem.2005.10.015. PMID   16321410.
  5. ↑ Parton, K; Gardner, D; Williamson, N.B (1996). "Isocupressic acid, an abortifacient component of Cupressus macrocarpa". New Zealand Veterinary Journal. 44 (3): 109–111. doi:10.1080/00480169.1996.35946. PMID   16031906.
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