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When we discuss the terpenes we are most interested in the carbon skeleton.

Terpenes. When we discuss the terpenes we are most interested in the carbon skeleton. Terpenes contain carbon atoms in multiples of five They are made by joining together 5-carbon isoprene units Oxygen-containing terpenes are sometimes called terpenoids. Terpenes.

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When we discuss the terpenes we are most interested in the carbon skeleton.

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  1. Terpenes • When we discuss the terpenes we are most interested in the carbon skeleton. • Terpenes contain carbon atoms in multiples of five • They are made by joining together 5-carbon isoprene • units • Oxygen-containing terpenes are sometimes called • terpenoids

  2. Terpenes Based on the isoprene structure • Know nomenclature • Understand linkage modes • See structures in Figure • All sterols (including cholesterol) are terpene-based molecules • Steroid hormones are terpene-based

  3. Isoprene Isoprene

  4. Head Isoprene Tail Head Tail

  5. The Isoprene Rule

  6. Head Isoprene Tail Head Tail

  7. Terpene Classification Class Name Isoprene Units Carbon Number • Monoterpene 2 10 • Sesquiterpene 3 15 • Diterpene 4 20 • Triterpene 6 30

  8. CH OH 2 -Terpinene a Monoterpene Examples O Myrcene Geraniol Cineole O O O OH Thujone Carvone Menthone Menthol

  9. Sesquiterpene Examples

  10. Representative Diterpenes

  11. Representative Triterpenes

  12. -Pinene a -Selinene b Isoprene Units in Terpenes O Limonene Camphor OH Guaiol

  13. -Pinene a -Selinene b Isoprene Units in Terpenes O Limonene Camphor OH Guaiol

  14. -Pinene a -Selinene b Isoprene Units in Terpenes O Limonene Camphor OH Guaiol

  15. -Pinene a -Selinene b Isoprene Units in Terpenes O Limonene Camphor OH Guaiol

  16. -Pinene a -Selinene b Isoprene Units in Terpenes O Limonene Camphor OH Guaiol

  17. Non-Isoprenoid Terpenes

  18. Steroids • Based on a core structure consisting of three 6-membered rings and one 5-membered ring, all fused together. • The B, C, and D rings are trans fused • Methyl groups at C-10 and C-13 are called angular methyl groups • Cholesterol is the most common steroid in animals and precursor for all other steroids in animals. • Steroid hormones serve many functions in animals - including salt balance, metabolic function and sexual function.

  19. Steroids • All steroids contain a tetracyclic ring system • Many hormones are steroids • Hormones are chemical messengers

  20. An A-B cis steroid

  21. The B, C, and D rings are trans fused Methyl groups at C-10 and C-13 are called angular methyl groups

  22. Figure 8.19 The structure of cholesterol, shown with steroid ring designations and carbon numbering.

  23. Cholesterol Is a Steroid

  24. Examples of Steroids

  25. Biosynthesis of Cholesterol

  26. Biosynthesis of Cholesterol

  27. Examples of Synthetic Steroids

  28. Practice Problem #1 • For each of the example terpenes given to you, find the isoprene units that are contained in the carbon skeleta.

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