labdane

{{chembox

| 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 = {{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=

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|Section3={{Chembox Hazards

| MainHazards=

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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.{{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 }}{{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 }}

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