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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 • 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.
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.
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
Which one of the following is a triacylglycerol (triglyceride), a fat? A) B) C) D) Question
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
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
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.
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
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
Prostaglandins • Prostaglandins are involved in many biological processes. • Are biosynthesized from linoleic acid (C18) via arachidonic acid (C20).
Diterpenes & PainAspirin’s Mode of Action - Prostaglandin Cascades
Aspirin Inhibits the Synthesis of Prostaglandins (prostaglandin endoperoxide synthase)