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CHAPTER 11 Terpenes

CHAPTER 11 Terpenes. Learning outcomes. Terpenes are unsaturated compounds formed by joining together isoprene units. Terpenes are components of a wide variety of fruit and floral flavours and aromas. Terpene derivatives are responsible for the distinctive aroma of spices. Terpenes.

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CHAPTER 11 Terpenes

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  1. CHAPTER 11Terpenes

  2. Learning outcomes • Terpenes are unsaturated compounds formed by joining together isoprene units. • Terpenes are components of a wide variety of fruit and floral flavours and aromas. • Terpene derivatives are responsible for the distinctive aroma of spices.

  3. Terpenes • The name ‘terpene’ is derived from the Greek word ‘terebinth’. • Terebinth is a type of pine tree from which terpene-containing resins are obtained.

  4. What are terpenes? • Natural organic compounds. • Components of a variety of fruit and floral flavours and aromas. • Used in perfumes, essential oils and medicines.

  5. Essential oils contain terpenes • Lavender – used to relieve tension. • Ylang-ylang – used to treat anxiety. • Lemon oil – aids good circulation. • Essential oils often contain a mixture of terpenes.

  6. Spices contain terpenes • Terpenes in plants can be oxidised to produce the compounds responsible for the distinctive aroma of spices. • Terpenes containing oxygen or other functional groups are known as ‘terpenoids’. • Common spices containing terpenes include cloves, cinnamon and ginger.

  7. Terpenes are unsaturated • Terpenes are unsaturated compounds. • All terpenes are built up from units of isoprene.

  8. Isoprene • Isoprene is the common name for 2-methylbuta-1,3-diene

  9. Building terpenes from isoprene Isoprene units can be linked: • head to tail to form linear terpenes • in rings to form cyclic terpenes.

  10. Isoprene

  11. Head Isoprene Tail Head Tail

  12. Head Isoprene Tail Head Tail

  13. Classification of Terpenes

  14. The Isoprene Unit • The isoprene units of myrcene are joined "head-to-tail." head tail tail head

  15. OH O H Representative Monoterpenes a-Phellandrene(eucalyptus) Menthol(peppermint) Citral(lemon grass)

  16. OH O H Representative Monoterpenes a-Phellandrene(eucalyptus) Menthol(peppermint) Citral(lemon grass)

  17. Representative Monoterpenes a-Phellandrene(eucalyptus) Menthol(peppermint) Citral(lemon grass)

  18. Limonene – a cyclic terpene

  19. Menthol – a cyclic terpenoid This terpene has been oxidised to a terpenoid

  20. Representative Sesquiterpenes H a-Selinene(celery)

  21. Representative Sesquiterpenes H a-Selinene(celery)

  22. Representative Sesquiterpenes a-Selinene(celery)

  23. a-Selinene – a cyclic terpene 3 isoprene units 15 carbon atoms

  24. OH Representative Diterpenes Vitamin A

  25. OH Representative Diterpenes Vitamin A

  26. Representative Diterpenes Vitamin A

  27. Diterpenes

  28. Representative Triterpene tail-to-tail linkage of isoprene units Squalene(shark liver oil)

  29. β-carotene – a linear terpene 8 isoprene units 40 carbon atoms

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