# Labdane

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Labdane
> Markdown URL: https://mediated.wiki/source/Labdane.md
> Source: https://en.wikipedia.org/wiki/Labdane
> Source revision: 1316507441
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{chembox
| verifiedrevid = 443914554
| ImageFile=labdane.svg
| ImageSize=150px
| IUPACName=Labdane
| SystematicName=(4a''R'',5''S'',6''S'',8a''S'')-1,1,4a,6-Tetramethyl-5-[(3''R'')-3-methylpentyl]decahydronaphthalene
| OtherNames=
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| 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 = {{stdinchicite|correct|chemspider}}
| 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 = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LEWJAHURGICVRE-AISVETHESA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=561-90-0
| PubChem=9548711
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1087749
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 36505
| SMILES = C2CC([C@@H]1CC[C@@H]([C@@H]([C@@]1(C)C2)CC[C@H](C)CC)C)(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](/source/diterpene).  It forms the structural core for a wide variety of [natural product](/source/natural_product)s collectively known as ''labdanes'' or ''labdane diterpenes''.  The labdanes were so named because the first members of the class were originally obtained from [labdanum](/source/labdanum), a resin derived from the [gum rockrose](/source/Cistus_ladanifer).<ref>{{cite journal|author1=Cocker, J. D. |author2=Halsall, T. G. |author3=Bowers, A. |title=The chemistry of gum labdanum. I. Some acidic constituents|journal=Journal of the Chemical Society|year=1956|pages=4259–62|doi=10.1039/jr9560004259 }}</ref><ref>{{cite journal|author1=Cocker, J. D. |author2=Halsall, T. G. |title=The chemistry of gum labdanum. II. The structure of labdanolic acid|journal=Journal of the Chemical Society|year=1956|pages=4262–71|doi=10.1039/jr9560004262 }}</ref>

A variety of biological activities have been determined for labdane diterpenes including antibacterial, antifungal, antiprotozoal, and anti-inflammatory activities.<ref>{{cite book | title = Studies in Natural Product Chemistry : Bioactive Natural Products, Part F | editor = Atta-Ur-Rahman | isbn = 978-0-08-044001-9| year = 1988 }}</ref> Natural labdanes in [tree](/source/tree) [resin](/source/resin) are believed to be the precursors of [amber](/source/amber), which polymerise under great pressure.

== Example labdane derivatives==
* [Forskolin](/source/Forskolin)
* [Galanolactone](/source/Galanolactone)<ref>{{cite journal |last1=Kenmogne |first1=Marguerite |last2=Prost |first2=Elise |last3=Harakat |first3=Dominique |last4=Jacquier |first4=Marie-José |last5=Frédérich |first5=Michel |last6=Sondengam |first6=Lucas B. |last7=Zèches |first7=Monique |last8=Waffo-Téguo |first8=Pierre |title=Five labdane diterpenoids from the seeds of Aframomum zambesiacum |journal=Phytochemistry |date=1 March 2006 |volume=67 |issue=5 |pages=433–438 |doi=10.1016/j.phytochem.2005.10.015 |pmid=16321410 |bibcode=2006PChem..67..433K }}</ref>
* [Isocupressic acid](/source/Isocupressic_acid) - is an abortifacient component of ''[Cupressus macrocarpa](/source/Cupressus_macrocarpa)''.<ref>{{Cite journal | doi = 10.1080/00480169.1996.35946| pmid = 16031906| title = Isocupressic acid, an abortifacient component of ''Cupressus'' macrocarpa| journal = New Zealand Veterinary Journal| volume = 44| issue = 3| pages = 109–111| year = 1996| last1 = Parton| first1 = K| last2 = Gardner| first2 = D| last3 = Williamson| first3 = N.B| url = https://zenodo.org/record/1234401}}</ref>
*[Medigenin](/source/Medigenin)
*[Sclareol](/source/Sclareol)
* [Stemodene](/source/Stemodene)

== See also ==
* [Abietane](/source/Abietane)

==References==
{{reflist}}

Category:Diterpenes
Category:Decalins

---
Adapted from the Wikipedia article [Labdane](https://en.wikipedia.org/wiki/Labdane) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Labdane?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.