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Lipids

Lipids. Lipids. Lipids are natural products more soluble in nonpolar solvents than in water. Some of them are related in that they have acetic acid (acetate) as their biosynthetic origin. Acetyl coenzyme A serves as the source of acetate.

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Lipids

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  1. Lipids

  2. Lipids • Lipids are natural products more soluble in nonpolar solvents than in water. • Some of them are related in that they have acetic acid (acetate) as their biosynthetic origin. • Acetyl coenzyme A serves as the source of acetate. • Some of them are related in that they have isoprene as their biosynthetic origin.

  3. Fats, Oils, and Fatty Acids

  4. O CH2OCR' O RCOCH CH2OCR" O Fats and Oils • Fats and oils are naturally occurring mixture of triacylglycerols (also called triglycerides). • Fats are solids; oils are liquids.

  5. O O CH2OCR CH2OH O O HOCR R'COCH HOCH R'COH CH2OCR" CH2OH HOCR" O O Fatty Acids • Acids obtained by the hydrolysis of fats and oils are called fatty acids. • Fatty acids usually have an unbranched chain with an even number of carbon atoms. • If double bonds are present, they are almost always cis. H2O

  6. Which one of the following is a triacylglycerol (triglyceride), a fat? A) B) C) D) Question

  7. Question • Which of the following is not an expected product of the acid hydrolysis of fats? • A) CH3(CH2)12CO2H • B) HOCH2CH2(OH)CH2OH • C) CH3(CH2)16CO2H • D) CH3(CH2)14CO2H

  8. O OH H H H H H H H H Fatty Acids Systematic name: (5Z, 8Z, 11Z, 14Z)-5,8,11,14- Icosatetraenoic acid Common name: Arachidonic acid

  9. Phospholipids

  10. Waxes

  11. Waxes • Waxes are water-repelling solids that coat the leaves of plants, etc. • Structurally, waxes are mixtures of esters. The esters are derived from fatty acids and long-chain alcohols.

  12. O CH3(CH2)14COCH2(CH2)28CH3 Waxes • Waxes are water-repelling solids that coat the leaves of plants, etc. • Structurally, waxes are mixtures of esters. The esters are derived from fatty acids and long-chain alcohols. Triacontyl hexadecanoate: occurs in beeswax

  13. Question • When cetyl palmitate is subjected to saponification conditions (NaOH, H2O, heat) which two compounds will be formed? • A) CH3(CH2)15OH + HOCH2(CH2)14CH3 • B) CH3(CH2)14CO2Na + NaO2C(CH2)14CH3 • C) CH3(CH2)14CO2H + HOCH2(CH2)14CH3 • D) CH3(CH2)15OH + NaO2C(CH2)14CH3

  14. Prostaglandins

  15. Prostaglandins • Prostaglandins are involved in many biological processes. • Are biosynthesized from linoleic acid (C18) via arachidonic acid (C20).

  16. Diterpenes & PainAspirin’s Mode of Action - Prostaglandin Cascades

  17. Aspirin Inhibits the Synthesis of Prostaglandins (prostaglandin endoperoxide synthase)

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