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Terpenes: The Isoprene Rule

Terpenes: The Isoprene Rule. Isoprene Links Heads or Tails?. Head to tail couplings are most common. Common Carbon Backbone. Some Common Terpenes. Terpenes. Classification of Terpenes. Class Number of carbon atoms Monoterpene 10 Sesquiterpene 15 Diterpene 20 Sesterpene 25

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Terpenes: The Isoprene Rule

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  1. Terpenes: The Isoprene Rule

  2. Isoprene LinksHeads or Tails? • Head to tail couplings are most common.

  3. Common Carbon Backbone

  4. Some Common Terpenes

  5. Terpenes Classification of Terpenes • Class Number of carbon atoms • Monoterpene 10 • Sesquiterpene 15 • Diterpene 20 • Sesterpene 25 • Triterpene 30 • Tetraterpene 40

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

  7. Terpenes Representative Sesquiterpenes H a-Selinene(celery)

  8. OH Terpenes Representative Diterpenes Vitamin A

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

  10. Terpenes • isoprenyl (C5) --> geranyl (C10) • geranyl (C10) --> farnesyl (C15) • farnesyl (C15) --> squalene (C30) • Generic: C10 monoterpenes, C15sesquiterpenes, C20 diterpenes, C30 triterpenes, C40 tetraterpenes

  11. + OPP OPP Cyclization • Rings form by intramolecular carbon-carbon bond formation. E double bond Z double bond

  12. + – H + Limonene OH H2O a-Terpineol

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