BU BI 421 - Lesson 1 Lipid Structure and Nomenclature

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group carbons qg q g Hydrocarbon a nam g 0 gzq 2 g cid 15482 p g Alkylsideohain 16 Lipids Structurally Diverse Class a era d i a o O UMMMM y mmm a sphingosine Fatty acid a am y n y pa m y g yag amlxedtriacylglycerol Classification Of Lipids Head group substituent Lipids that contain fatty acids complex lipids further separated into Storage lipids membrane lipids d Ubiquinone amitochondrial electron Carrierecoenzyme n u l at y 9 46 1 on c yn I Lipids that do not contain fatty acids group 18 10 34T steroid nucleus 4 7 4 1 I tII FET F Poa cid 15483 H cholesterol Vitamins pigments etc Fatty acid Fatty acid so fattyacid Fatty acid Fatty acid n Mono or Fatty acid Poy Alcohol Poa choline oligosaccharide Fatty acid Fatty acid Dlphytanyl g Piphytanyl E Mono or disaccharide 1504 Poc 1 ether linkage Aaas 5 Building blocks of fats Carboxylic acids with hydrocarbon chains containing 4 36 carbons Hydrocarbon almost all natural fatty acids have an even of carbons group i cid 15483 Chain 8 99 9 9 ao cid 15483 F Casa most natural fatty acids are unbranched saturated no double bond between carbons in 1h alkyl chain Monounsaturated one double bond between carbons in the alkyl chains trans Oleic acid Polyunsaturated more than one double bond in the alkyl chain saturated unsaturated 0 Hohman HO Iy Cls Oleic acid 7 Fatty Acid Nomenclature Example Trivial names or common names Oleic Acid ex 10 1 19 cis a Octadecenoic add Systematic names or IUPAC names 192 Octadec 9 enoic acid AX Delta x nomenclature I Cis A Octadecenoic acid N x Nminus x w x or omega x nomenclature ston Carbons 18 159 Double Bond LOCATION of Double Bonds 12 sili 13 Omega 9 fattyacid 0 11 18 1 n 9 or 18 1 w a I Y Si Ho w S paByS6209 is is a stainisto iP 18 1w 9 18 1 C1S 9 Fatty Acid Nomenclature Table Some Naturally Occurring Fatty Acids Structure Properties and Nomenclature Carbon skeleton structure a systematic named common name derivation Melting point Water Benzene 12 0 14 0 16 0 18 0 20 0 24 0 16 1 AP 18 1 99 18 2 94 12 18 3 19 12 15 20 4 15 8 11 14 CH3 CH2 ioCOOH CHy CHe in COOH CH3 CH2 14COOH CH3 CHe isCOOH CH3 CH2 COOH CH3 CHe zzCOOH n bodecanoic acid Lauriad n Tetradecanoic acid n Hexadecanoic acid Myristic acid palmitic acid noctadecanoic acid stearic acid n Eicosanoic acid notetracosanoiacid Arachidic acid lignocer acid CHICHe CH CHICHe COOH cIs 9 Octadecenoic acid Oleicacid CH3 CHe yCH CHCHeCH CH CHe COOH cisias 912 Octadecadenoic acId Linoleicald CHyCHeCH CHCH2CH CHCHECH CHCCHe COOHOctadecatrienoic acid CIS CIS C15 9 12 15 Linolenic acid CH3 CH2 pCH CHCHeCH CHCH2CH CHCHeCH CH CHelsCOOH CISCIS CS CIS S 8 11 14 Icosatetraenoicacid CHy CHe sCH CH CHe COOH Cis 9 Hexadecenoic acid Palmitolecacid 1 t0 0 S Arachidonic acid 49 5 I C 44 2 53 9 63 1 69 6 76 5 86 0 13 4 1 5 211 solubility at30 mg gsolvents 0 003 0 024 0 0083 0 0034 2 600 874 348 124


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