lipids - LIPIDS METABOLISM Lipids Definition water...

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LIPIDS METABOLISM
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Lipids Definition: water insoluble compounds Most lipids are fatty acids or ester of fatty acid They are soluble in non-polar solvents such as petroleum ether, benzene, chloroform Functions Energy storage Structure of cell membranes Thermal blanket and cushion Precursors of hormones (steroids and prostaglandins) Enzyme cofactors Membrane anchors for proteins Signalling messengers Electron carriers Pigments (photosynthesis and vision) Emulsifier agents (digestion and blood transport)
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PROPER LIPIDS Proper lipids – ester of fatty acid and glycerol, Mono, di, tri- acylglycerols, also termed glycerides Glycerol is a polyalcohol
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GLYCERIDES O OH OH R O O OH O R O R O O O R O R O O R O MONOGLYCERIDE DIGLYCERIDE TRIGLYCERIDE Three fatty acids can form esters with glycerol - the 3 FA can be of the same type (simple triacylglycerols) - the 3 FA can be different (complex triacylglycerols)
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Fatty acids - linear hydrocarbon chains of various lengths (4 to 36 C) with a carboxylic group at the end - Saturated (all single bonds) or unsaturated (one or more double bonds) - hydrocarbon chain can have substituents (OH, methyl groups, 3 carbon rings) - Nomenclature: length of the chain, column, number of double bonds, delta with positions of the double bonds as superscription brackets. - e.g. C18:1 (Δ9) = oleic acid, 18 carbon fatty acid with a double bond positioned at the ninth carbon counting from and including the carboxyl carbon (between carbons 9 and 10)
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- have even number of carbons because are synthesized by condensation of acetyl (2C) groups - most common have chains between 12 and 24 C - double bonds of polyunsaturated fatty acids are not conjugated (separated by a methylene group) CH=CH-CH2-CH=CH - double bonds usually in „cis” configuration - the most common position for the first double bond is C9, and following double bonds in C12 and C15, but there are exceptions (CH 2 )n CH 3 COOH n is almost always even n = 0 : CH 3 COOH n = 1 : propionic acid
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Saturated fatty acids lower - acetate CH 3 COOH - butyric C 3 H 7 COOH - valeric C 4 H 7 COOH - caproic C 5 H 11 COOH - caprylic C 7 H 15 COOH - capric C 9 H 19 COOH higher - lauric C 11 H 23 COOH - myristic C 13 H 27 COOH - palmitic C 15 H 31 COOH - stearic C 17 H 35 COOH - arachidic C 19 H 39 COOH - behenic C 21 H 43 COOH
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Unsaturated fatty acids oleic – 18:1 (9) linoleic – 18:2 (9, 12) linolenic – 18:3 (9, 12, 15) arachidonic – 20:4 (5, 8, 11, 14)
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Common Name Systematic Name Formula Common source II. Unsaturated Fatty Acids A. Monoethenoic Acids Oleic Cis 9-octadecenoic C17H33COOH plant and animal fats Elaidic Trans 9-Octadecenoic C17H33COOH animal fats B. Diethenoic Acids Linoleic 9,12-Octadecadienoic C17H31COOH peanut, linseed, and cottonseed oils C. Triethenoid Acids Linolenic 9,12,15-Octadecatrienoic C17H29COOH linseed and other seed oils Eleostearic 9,11,13-Octadecatrienoic C17H29COOH peanut seed fats D. Tetraethenoid Acids Moroctic 4,8,12,15- Octadecatetraenoic C17H27COOH fish oils Arachidonic 5,8,11,14- Eicosatetraenoic C19H31COOH traces in animal fats
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Essential Fatty Acids
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