Cadinenes: Difference between revisions

| verifiedrevid = 439047023

| Name = Cadinenes

| ImageFile = Alpha_cadinene.png

| ImageSize = 135px

| ImageName = α-cadinene

| ImageCaption = α-Cadinene

| ImageFile1 = Gamma-cadinene.png

| ImageSize1 = 135px

| ImageCaption1 = γ-Cadinene

| ImageFile2 = Delta cadinene.png

| ImageSize2 = 135px

| ImageCaption2 = δ-Cadinene

| IUPACName = · (1''S'',4a''R'',8a''R'')-4,7-dimethyl-1-(propan-2-yl)-

1,2,4a,5,6,8a-hexahydronaphthalene (α-cadinene)<br>· (1''S'',4a''R'',8a''R'')-7-methyl-4-methylidene-1-(propan-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene (&gamma;-cadinene)<br>· (1''S'',8a''R'')-4,7-dimethyl-1-(propan-2-yl)-1,2,3,5,6,8a-hexahydronaphthalene (&delta;-cadinene)

| IUPACName_hidden = yes

| CASNo = 24406-05-1

| CASNo_Comment = (α-cadinene)

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo1 = 39029-41-9

| CASNo1_Comment = (&gamma;-cadinene)

| CASNo1_Ref = {{cascite|correct|CAS}}

| CASNo2 = 483-76-1

| CASNo2_Comment = (&delta;-cadinene)

| CASNo2_Ref = {{cascite|correct|CAS}}

| C = 15 | H = 24

| Density =

| MeltingPt =

| BoilingPt =

'''Cadinene''' is the trivial chemical name of a number of [[isomer]]ic [[hydrocarbon]]s that occur in a wide variety of [[essential oil]]-producing plants. The name is derived from that of the [[Juniperus oxycedrus|Cade juniper (''Juniperus oxycedrus'' L.)]], the wood of which yields an oil from which cadinene isomers were first isolated.

Chemically, the cadinenes are [[Bicyclic molecule|bicyclic]] [[sesquiterpene]]s. The term “cadinene” has sometimes been used in a broad sense to refer to any sesquiterpene with the so-called cadalane (4-isopropyl-1,6-dimethyldecahydronaphthalene) carbon skeleton. Because of the large number of known double-bond and stereochemical isomers, this class of compounds has been subdivided into four subclasses based on the [[Stereochemistry|relative stereochemistry]] at the isopropyl group and the two [[Bicyclic molecule|bridgehead]] carbon atoms.<ref>

|author = A.-K. Borg-Karlson, T. Norin and A. Talvitie

|title = Configurations and conformations of torreyol (δ-cadinol), α-cadinol, T-muurolol and T-cadinol

|journal = [[Tetrahedron]]

|volume = 37 |pages = 425–430

|year = 1981

|doi = 10.1016/s0040-4020(01)92031-9

|issue = 2

}}</ref> The name ''cadinene'' is now properly used only for the first subclass below, which includes the compounds originally isolated from [[Juniperus oxycedrus|cade oil]]. Only one [[enantiomer]] of each subclass is depicted, with the understanding that the other enantiomer bears the same subclass name.

Image:Cadinane.svg|Cadinene stereochemistry

Image:Muurolane.svg|Muurolene stereochemistry

Image:Amorphane.svg|Amorphene stereochemistry

Image:Bulgarane.svg|Bulgarene stereochemistry

[[Category:Alkenes]]

[[ca:Cadinè]]

[[de:Cadinene]]

[[ru:Кадинен]]