Terpene

Terpenes are aromatic compounds found in many plants, including cannabis, contributing to their distinct scents. They play a key role in the plant’s defense mechanisms and in attracting pollinators. In cannabis, terpenes are significant for their potential therapeutic effects and for influencing the plant’s overall effect on users, known as the “entourage effect.”

History and Terminology

• The term ‘terpene’ was coined by German chemist August Kekulé in 1866.
• Terpene is a shortened form of terpentine, an obsolete spelling of turpentine.
• Terpenoids are modified terpenes with additional functional groups.
• Terpenes and terpenoids have strong odors for protection or attraction.
• Leopold Ružička won the 1939 Nobel Prize for his work on higher terpenes.

Biological Function

• Terpenes are biosynthetic building blocks.
• Terpenes mediate ecological interactions in plants.
• Terpenoids play roles in cell growth, light harvesting, and more.
• Trees release more terpenes in warmer weather for cloud seeding.
• Some insects use terpenes for defense mechanisms.

Applications

• Natural rubber (polyisoprene) is a major terpene with various applications.
• Turpentine and rosin are commercial terpene products.
• Terpenes are used in fragrances, flavors, and consumer products.
• Some terpenes form hydroperoxides for polymer production.
• Terpenes have pharmacological effects and are used in traditional medicines and pesticides.

Physical and Chemical Properties

• Terpenes are colorless, non-polar, and flammable.
• Boiling points increase with molecular size.
• Terpenoids are more polar and slightly soluble in water.
• Derivatives of terpenoids like glycosides are water-soluble solids.
• Terpenes can cause irritation and gastrointestinal disturbances if ingested.

Biosynthesis and Structure

• Terpenes follow the biogenetic isoprene rule.
• Isoprene units DMAPP and IPP are building blocks for terpenes.
• Terpenes result from linking isoprene units head to tail, with structural diversity arising from isomerism.
• Chirality is common in terpenes and terpenoids, with most exhibiting unsaturation with C=C groups.
• Terpenes are classified by the number of isoprene units, with monoterpenes having 2 isoprene units (C10) and triterpenes having 6 isoprene units (C30).

Terpene Data Sources