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Terpinene

(terpinolene) β: 4-Methylene-1-(1-methylethyl)cyclohexene γ: 4-Methyl-1-(1-methylethyl)-1,4-cyclohexadiene δ: 1-Methyl-4-(propan-2-ylidene)cyclohex-1-ene β: 0.838 g/cm3 γ: 0.853 g/cm3 β: 173-174 °C γ: 183 °C

The terpinenes are a group of isomeric hydrocarbons that are classified as monoterpenes. They each have the same molecular formula and carbon framework, but they differ in the position of carbon-carbon double bonds. α-Terpinene has been isolated from cardamom and marjoram oils, and from other natural sources. β-Terpinene has no known natural source but has been prepared from sabinene. γ-Terpinene and δ-terpinene (also known as terpinolene) have been isolated from a variety of plant sources. They are all colorless liquids with a turpentine-like odor.

Production and uses

α-Terpinene is produced industrially by acid-catalyzed rearrangement of α-pinene. It has perfume and flavoring properties but is mainly used to confer pleasant odor to industrial fluids. Hydrogenation gives the saturated derivative p-menthane.

Biosynthesis of α-terpinene

The biosynthesis of α-terpinene and other terpenoids starts with the isomerization of geranyl pyrophosphate to linalyl pyrophosphate (LPP). LPP then forms a resonance-stabilized cation by loss of the pyrophosphate group. Cyclization is then completed thanks to this more favorable stereochemistry of the LPP cation, yielding a terpinyl cation. Finally, a 1,2-hydride shift via a Wagner-Meerwein rearrangement produces the terpinen-4-yl cation. It is the loss of a hydrogen from this cation that generates α-terpinene.

Plants that produce terpinene

  • Cuminum cyminum{{cite journal |display-authors=etal}}{{cite journal |display-authors=etal}}
  • Melaleuca alternifolia
  • Cannabis
  • Origanum syriacum
  • Coriandrum sativum
  • Monarda fistulosa

References

References

  1. {{cite encyclopedia. M. Eggersdorfer. (2005). Wiley-VCH
  2. Dewick, P. M.. (2009). "Medicinal Natural Products: A Biosynthetic Approach". John Wiley & Sons.
  3. (2017). "Structural and Chemical Biology of Terpenoid Cyclases". Chemical Reviews.
  4. Hillig, Karl W. (October 2004). "A chemotaxonomic analysis of terpenoid variation in Cannabis". Biochemical Systematics and Ecology.
  5. (2012-07-01). "Characterization of Coriander (Coriandrum sativum L.) Seeds and Leaves: Volatile and Non Volatile Extracts". International Journal of Food Properties.
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monoterpenes dienes cyclohexenes cyclohexadienes
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