α-Terpinene is a terpene produced through the acid-catalyzed rearrangement of α-pinene, also undergoing hydrogenation to form -menthane. It’s primarily utilized in industrial fluids and perfumes for its pleasant odor. The biosynthesis involves the isomerization of geranyl pyrophosphate and several chemical steps leading to α-terpinene. Plants like Cuminum cyminum and Cannabis, among others, produce terpinene. This compound is part of extensive research for its various uses and effects.
Production and Uses of Terpinene
- α-Terpinene is produced by acid-catalyzed rearrangement of α-pinene.
- Hydrogenation gives the saturated derivative -menthane.
- Mainly used in industrial fluids for its pleasant odor.
- Has perfume and flavoring properties.
Biosynthesis of α-Terpinene
- Biosynthesis starts with isomerization of geranyl pyrophosphate to linalyl pyrophosphate.
- Linalyl pyrophosphate forms a resonance-stabilized cation by losing the pyrophosphate group.
- Cyclization yields a terpinyl cation due to favorable stereochemistry.
- 1,2-hydride shift via Wagner-Meerwein rearrangement produces terpinen-4-yl cation.
- Loss of hydrogen from terpinen-4-yl cation generates α-terpinene.
Plants that Produce Terpinene
- Cuminum cyminum
- Melaleuca alternifolia
- Cannabis
- Origanum syriacum
- Coriandrum sativum
References
M. Eggersdorfer (2005). Terpenes.
Ullmanns Encyclopedia of Industrial Chemistry
Dewick, P. M. (2009). Medicinal Natural Products: A Biosynthetic Approach.
Christianson, David W. (2017). Structural and Chemical Biology of Terpenoid Cyclases.
Li, Rong; Zi-Tao Jiang (2004). Chemical composition of the essential oil of Cuminum cyminum L. from China.
Additional Information
- Wang, Lu; Wang, Z; Zhang, H; Li, X; Zhang, H; et al. (2009). Ultrasonic nebulization extraction coupled with headspace single drop microextraction and gas chromatography–mass spectrometry for analysis of the essential oil in Cuminum cyminum L.
- Iacobellis, Nicola S.; Lo Cantore, P; Capasso, F; Senatore, F; et al. (2005). Antibacterial Activity of Cuminum cyminum L. and Carum carvi L. Essential Oils.
- Hillig, Karl W (October 2004). A chemotaxonomic analysis of terpenoid variation in Cannabis.
- Shahwar, Muhammad Khuram; El-Ghorab, Ahmed Hassan; Anjum, Faqir Muhammad; Butt, Masood Sadiq; Hussain, Shahzad; Nadeem, Muhammad (2012-07-01). Characterization of Coriander (Coriandrum sativum L.) Seeds and Leaves: Volatile and Non Volatile Extracts.
Terpinene Data Sources
| Reference | URL |
|---|---|
| Glossary | https:/glossary/terpinene |
| Wikipedia | https://en.wikipedia.org/wiki/Terpinene |
| Wikidata | https://www.wikidata.org/wiki/Q424891 |
| Knowledge Graph | https://www.google.com/search?kgmid=/m/09b3zd |
| DBPedia | http://dbpedia.org/resource/Terpinene |
| Product Ontology | http://www.productontology.org/id/Terpinene |