Cadinene

Cadinene the (stress on the third syllable, Cadinene ) are a group of chiral compounds which differ by the position of the double bonds in the molecule, the configuration of the stereo centers and the connection of the two cyclohexane rings. There are unsaturated bicyclic hydrocarbons and belong to the series of sesquiterpenes. Allen is the structure of the saturated parent compound, the cadinane, based.

The name is derived from Juniperus oxycedrus (French Cade juniper, juniper), whose wood Cadinene were first isolated.

Depending on the stereochemical configuration of the individual representatives of the group of substances are also referred to as Muurolene, Amorphene or Bulgarene.

Representative

At the three stereogenic centers of the eight possible stereoisomers are all known, the most important and also the most common of all is sesquiterpene (-)- β - cadinene ( [ α ] D20 -251 °). It is a derivative of hexahydro- 4- isopropyl -1 ,6- dimethylnaphthalene ( Cadalin ), the saturated compound is known as strain cadinane.

Stereochemistry

Depending on the combination of the two cyclohexane - structural elements each representative of the group of materials are also known as Muurolene, Amorphene Bulgarene or a function of the absolute stereochemical configuration.

Configuration of Muurolene

Configuration of Amorphene

Configuration of Bulgarene

Cadinene are sensitive to light and should be kept in dark places.

Occurrence and extraction

(-)- Β - cadinene is to find, among other things in the essential oil of Kubebenpfeffers and in the leaves of some germander species. It is the main component of Cade oil which is obtained by dry distillation of juniper (Juniperus oxycedrus ) in the Mediterranean. Its isomer γ - cadinene occurs in goldenrod species.

Use

• Ointments for skin rashes
• Teerseifen
• Hair albums
• β - cadinene is used as a flavoring in baked goods, candy and chewing gum, as well as a fragrance in cosmetics and detergents.