Sabinene is a natural bicyclic

monoterpene Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen func ...

with the molecular formula C₁₀H₁₆. It is isolated from the essential oils of a variety of plants including

Marjoram Marjoram (; ''Origanum majorana'') is a cold-sensitive perennial herb or undershrub with sweet pine and citrus flavours. In some Middle Eastern countries, marjoram is synonymous with oregano, and there the names sweet marjoram and knotted marj ...

, holm oak (''Quercus ilex'') and Norway spruce (''Picea abies''). It has a strained ring system with a

cyclopentane Cyclopentane (also called C pentane) is a highly flammable alicyclic hydrocarbon with chemical formula C5H10 and CAS number 287-92-3, consisting of a ring of five carbon atoms each bonded with two hydrogen atoms above and below the plane. It occu ...

ring fused to a cyclopropane ring. Sabinene is one of the chemical compounds that contributes to the spiciness of

black pepper Black pepper (''Piper nigrum'') is a flowering vine in the family Piperaceae, cultivated for its fruit, known as a peppercorn, which is usually dried and used as a spice and seasoning. The fruit is a drupe (stonefruit) which is about in dia ...

and is a major constituent of carrot seed oil. It also occurs in tea tree oil at a low concentration. It is also present in the essential oil obtained from nutmeg, ''

Laurus nobilis ''Laurus nobilis'' is an aromatic evergreen tree or large shrub with green, glabrous (smooth) leaves. It is in the flowering plant family Lauraceae. It is native to the Mediterranean region and is used as bay leaf for seasoning in cooking. ...

'', and ''

Clausena anisata :''Should not be confused with syzygium anisatum, a tree native to eastern Australian rainforests, used as a culinary herb.'' ''Clausena anisata'' (Willd.) Hook.f. ex Benth. is a deciduous shrub or small tree, belonging to the Rutaceae or Citr ...

''.

Biosynthesis

Sabinene, a bicyclic monoterpene, is present in the (+) and (-) enantiomers. It is biosynthesized from the common terpenoid precursor,

geranyl pyrophosphate Geranyl pyrophosphate (GPP), also known as geranyl diphosphate (GDP), is the pyrophosphate ester of the terpenoid geraniol. Its salts are colorless. It is a precursor to many natural products. Occurrence GPP is an intermediate in the isopreno ...

(GPP) that undergoes polycyclization catalyzed by sabinene synthase (SabS). GPP is formed from the terpenoid synthesis pathway with the starter units,

isopentenyl pyrophosphate Isopentenyl pyrophosphate (IPP, isopentenyl diphosphate, or IDP) is an isoprenoid precursor. IPP is an intermediate in the classical, HMG-CoA reductase pathway (commonly called the mevalonate pathway) and in the ''non-mevalonate'' MEP pathway of i ...

(IPP) and

dimethylallyl pyrophosphate Dimethylallyl pyrophosphate (DMAPP; or alternatively, dimethylallyl diphosphate (DMADP); also isoprenyl pyrophosphate) is an isoprenoid precursor. It is a product of both the mevalonate pathway and the MEP pathway of isoprenoid precursor biosynt ...

(DMAPP). The starter units, IPP and DMAPP, can be synthesized from either the mevalonate (MVA) or the methylerythritol 4-phosphate (MEP) pathway. With the head-to-tail condensation of IPP and DMAPP catalyzed by GPP synthase, GPP is formed. Sabinene synthase (SabS) then catalyzes the ionization and isomerization of GPP to form 3R-linalyl pyrophosphate. Further ionization and cyclization results in the formation of sabinene. Sabinene BIosynthesis

References

Hydrocarbons Alkene derivatives Monoterpenes Cyclopropanes Cyclopentanes Isopropyl compounds {{hydrocarbon-stub

Biosynthesis

See also

References