Sclarene

Diterpenes are terpenes made of four isoprene units, often with the molecular formula C20H32. Sclarene is one of the diterpenes with two rings, as is labdane. The molecular weight of sclarene is 272.5. Diterpenes are biosynthesized by plants, animals and fungi, with geranylgeranyl pyrophosphate as a primary intermediate.

Sclareol is a bicyclic diterpene alcohol found in Salvia sclarea. Sclareol is extracted by steam distillation of fresh flowers, then purified by further extraction using an organic solvent. It is the most common starting material for manufacturing ambroxide, which is used as a fixative in commercial perfumes.

A different material, with the formula C13H21NO and the chemical name 4,5-decamethyleneoxazole, is sold under the trade name Sclarene. That product is a colourless liquid with a molecular weight of 207.3.

The systematic name of sclarene is (4aS,8S,8aS)-4,4,8a-trimethyl-7-methylidene-8-(3-methylidenepent-4-enyl)-2,3,4a,5,6,8-hexahydro-1H-naphthalene. The compound is also written (+)-sclarene.

Strictly, diterpenes are hydrocarbons and contain no heteroatoms. Functionalized structures should be called diterpenoids, although the two terms are often used interchangeably in scientific literature. The number of rings divides diterpenes broadly: phytane has none, cembrene A has one, abietane and taxadiene have three, and stemarene and stemodene have four.

Salvia sclarea, the clary or clary sage, is a short-lived herbaceous perennial native to the northern Mediterranean Basin and to some areas in North Africa and Central Asia. It is currently grown for its essential oil. Sclareol is mainly produced in the glandular trichomes of sage flower calyces.

Ambroxide is a naturally occurring terpenoid and one of the key constituents responsible for the odor of ambergris. It is an autoxidation product of ambrein.

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