Labdane

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title: "Labdane" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["diterpenes", "decalins"] topic_path: "general/diterpenes" source: "https://en.wikipedia.org/wiki/Labdane" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| verifiedrevid = 443914554 | ImageFile=labdane.svg | ImageSize=150px | IUPACName=Labdane | SystematicName=(4aR,5S,6S,8aS)-1,1,4a,6-Tetramethyl-5-[(3R)-3-methylpentyl]decahydronaphthalene | OtherNames= |Section1={{Chembox Identifiers | ChemSpiderID_Ref = | ChemSpiderID = 7827634 | 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 | InChIKey = LEWJAHURGICVRE-AISVETHEBV | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = LEWJAHURGICVRE-AISVETHESA-N | CASNo_Ref = | CASNo=561-90-0 | PubChem=9548711 | ChEMBL_Ref = | ChEMBL = 1087749 | ChEBI_Ref = | ChEBI = 36505 | SMILES = C2CC([C@@H]1CCC@@HC)(C)C |Section2={{Chembox Properties | C=20|H=38 | Appearance= | Density= | MeltingPt= | BoilingPt= | Solubility= |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt =

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.

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

Example labdane derivatives

References

References

  1. (1956). "The chemistry of gum labdanum. I. Some acidic constituents". Journal of the Chemical Society.
  2. (1956). "The chemistry of gum labdanum. II. The structure of labdanolic acid". Journal of the Chemical Society.
  3. (1988). "Studies in Natural Product Chemistry : Bioactive Natural Products, Part F".
  4. (1 March 2006). "Five labdane diterpenoids from the seeds of Aframomum zambesiacum". Phytochemistry.
  5. (1996). "Isocupressic acid, an abortifacient component of ''Cupressus'' macrocarpa". New Zealand Veterinary Journal.

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diterpenesdecalins