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LIPIDS Introduction

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LIPIDS Introduction LIPIDS Introduction Definition: water insoluble compounds • Most lipids are fatty acids or esters of fatty acids • They are soluble in non-polar solvents such as petroleum ether, benzene, chloroform Lipids Functions 1. Store energy: fat cells Thermal blanket 2. Chemical messengers: find in nerve fibers and hormones. 3. Parts of membranes: insoluble in water 4. Precursors of hormones (steroids and prostaglandins) Lipids There are 2 types of lipids; •those that contain the structural component of a fatty acid; and •those that contain the structural component of a four member steroid molecule. Lipids Lipids with fatty acids 1. Simple lipids: Store energy, insulation Triglycerides (Fats & Oils), Waxes Cell 2. Complex lipids Glycerophospholipids membrane Sphingolipids 3. Eicosanoids Pain, fever, inflammation Lipids without fatty acids Chemical messenger Steroids (Cholesterol & steroid hormones) Cell membrane Properties of fats and oils • fats are solids or semi solids • oils are liquids • melting points and boiling points are not usually sharp (most fats/oils are mixtures) • when shaken with water, oils tend to emulsify • pure fats and oils are colorless and odorless (color and odor is always a result of contaminants) – i.e. butter (bacteria give flavor, carotene gives color) Lipids Lipids can be categorized as: 1. Hydrolyzable lipids can be converted into small molecules by aqueous hydrolysis. Lipids Lipids can be categorized as: 2. Nonhydrolyzable lipids cannot be cleaved into smaller molecules by aqueous hydrolysis. Hydrolysis Most hydrolyzable lipids contain an ester. Hydrolysis: reaction with water. (breaking a bond and adding the elements of water) O O Heat RCOR' + H2O H+ or enzyme RC- OH + H-OR' An ester A carboxylic acid An alcohol Fatty acids • Fatty acids can be classified either as: ➢saturated (C-C bonds) or unsaturated (also C=C) ➢according to chain length: • short chain FA: 2-4 carbon atoms • medium chain FA: 6 –10 carbon atoms • long chain FA: 12 – 26 carbon atoms ➢ essential fatty acids vs those that can be biosynthesized in the body: – linoleic and linolenic are two examples of essential fatty acid – oleic, stearic – nonessential Fatty acids • Carboxylic acid are derivatives of long chain hydrocarbons COOH Stearic acid (18:0) (mp 70°C) – Nomenclature COOH Oleic acid (18;1) (mp 16°C) • Stearate – stearic acid – C18:0 – n-octadecanoic acid COOH Linoleic acid (18:2) – General structure of saturated fatty acids: (mp-5°C) COOHLinolenic acid (18:3) (mp -11°C) Cn H2n+1 COOH n - carbon atoms in a molecule Nomenclature of fatty acids SATURATED FATTY ACIDS Common name Systematic name Formula C4:0 Butyric Butanoic acid C3H7COOH C6:0 Caproic acid Hexanoic acid C5H11COOH C8:0 Caprylic acid Octanoic acid C7H15COOH C10:0 Capric acid Decanoic acid C9H19COOH C12:0 Lauric acid Dodecanoic acid C11H23COOH C14:0 Myristic acid Tetradecanoic acid C13H27COOH C16:0 Palmitic acid Hexadecanoic acid C15H31COOH C18:0 Stearic acid Octadecanoic acid C17H35COOH C20:0 Arachidic Eicosanoic acid C19H39COOH C24:0 Lignoceric acid Tetracosanoic acid C23H47COOH C16:0 Palmitic acid (C15H31COOH) Structural formula of palmitic acid CH3 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 COOH CH3(CH2)14COOH Condensed structural formula of palmitic acid O C OH Skeletal formula of palmitic acid Fatty acids Hydrolyzable lipids are derived from fatty acids. Fatty acids are: COOH Stearic acid (18:0) (mp 70°C) COOH Oleic acid (18;1) • Long-chain unbranched carbon (mp 16°C) attached to a carboxyl group (-COOH). COOH Linoleic acid (18:2) (mp-5°C) • Typically 12-20 carbon atoms. COOHLinolenic acid (18:3) (mp -11°C) • They have an even number of C atoms. COOH Stearic acid (18:0) (mp 70°C) • Insoluble in water. COOH Oleic acid (18;1) (mp 16°C) Cis COOH Linoleic acid (18:2) (mp-5°C) COOHLinolenic acid (18:3) (mp -11°C) Fatty acids CH3(CH2)14COOH (palmitic acid) polar portion = hydrophillic nonpolar portion = hydrophobic Hydrophobic portion is much bigger than hydrophilic portion. Insoluble in water Saturated and unsaturated Fatty acids Saturated fatty acids have no double bonds in their long hydrocarbon chains. Stearic acid: CH3(CH2)16COOH They are solids at room temperature. Packed together COOH COOH COOH COOH COOH Saturated and unsaturated Fatty acids Unsaturated fatty acids have 1 or more double bonds (generally cis) in their long hydrocarbon chains. Oleic acid: CH3(CH2)7CH=CH(CH2)7COOH They are liquids at room temperature. Kinks They can not pack together COOH COOH COOH COOH COOH Unsaturated fatty acids • Various conventions are in use for indicating the number and position of the double bond(s) 18 9 1 In chemistry H n (Δ) designation: H3C (CH2)7 C CH(CH2)7COOH 10 Carbon atom numbering starts from Δ = delta COOH group 18:1,9 or 9 18:1 2 3 4 5 6 7 8 9 10 18 In biochemistry: H3C CH2CH2CH2CH2CH2CH2CH2CH CH(CH2)7COOH ω designation n 17 10 9 1 ω = omega Carbon atom numbering starts from CH3 group 9, C18:1 or n-9, 18:1 Fatty acids • The human body is capable of synthesizing most fatty acids from carbohydrates or other fatty acids. • Humans do not synthesize sufficient amounts of fatty acids that have more than one double bond. • More than one double bond fatty acids are called essential fatty acids and they must be provided by the diet. Linoleic acid Linolenic acid The Essential Fatty Acids (EFA) are a group of fatty acids that are essential to human health (Omega 6) Fatty acids that contain at least two double bonds, one of them at C6 (carbon atom numbering starts from CH3 group). LINOLEIC ACID 18:2 (9,12) is main representative acid of this group (CH ) COOH H3C (CH2)4 CH2 2 7 1 8 18 CH CH CH CH 6 7 9 10 (Omega 3) Fatty acids that contain at least two double bonds, one of them at C3 (starting from CH3 group) LINOLENIC ACID 18:3 (9,12,15) is the basic acid of this group CH (CH ) COOH H3C CH2 2 CH2 2 7 1 2 5 18 CH CH CH CH CH CH 3 4 6 7 Essential Fatty acids Omega-n acids n: the position of the first double bond Linoleic acid is called an omega-6 acid, because of the position of the first C=C in the nonpolar chain. carbon atom numbering starts from CH3 group Essential Fatty acids Linolenic acid is called an omega-3 acid, because of the position of the first C=C in the nonpolar chain. Omega-3 sources: Omega-6 sources: Flaxeed oil/canola oil Corn oil Fish liver oils/Fish Peanut oil eggs Cottonseed oil Human Milk Soybean oil Seafood/Fatty fish Many plant oils - albacore tuna - mackerel - salmon -sardines ➢Proper n-6 to n-3 ratio in a diet is 4:1 Fatty acids • C3H7COOH butyric acid (butanoic acid) – short chain FA • Common medium-chain saturated fatty acids: C5H11COOH caproic acid (hexanoic acid) C7H15COOH caprylic acid (octanoic acid) C9H19COOH capric acid (decanoic acid) CH2 CH2 COOH 5 3 1 caproic acid H3C CH2 CH2 6 4 2 ➢ liquid (C1 to C6), solid (from C7) Fatty acids • common long-chain saturated FA’s: C11H23COOH : lauric acid (n-dodecanoic acid; C12:0) C13H27COOH : myristic acid (n-tetradecanoic acid; C14:0) C15H31COOH : palmitic acid (n-hexadecanoic acid; C16:0) C17H35COOH; stearic acid (n-octadecanoic acid; C18:0) C19H39COOH; arachidic (eicosanoic acid; C20:0) C23H47COOH; lignoceric acid C25H51COOH; cerotic acid Less common fatty acids H C 3 R= COOH R • R iso – isobutyric acid H3C H3C • odd carbon fatty acid – propionic acid CH3 • hydroxy fatty acids – ricinoleic acid, dihydroxystearic acid, cerebronic acid (found in higher plants) • cyclic fatty acids – hydnocarpic, chaulmoogric acid (nonedible fat and oil isolated from chaulmoogra oil, used in LEPROSY treatment) (CH2)12-CO2H (CH2)10-CO2H chaulmoogric acid hydnocarpic acid MonoUnsaturated fatty acids MUFA • Monoenoic acid (monounsaturated) Cn H2n-1 COOH There is free rotation about C-C bonds in the fatty acid hydrocarbon, except where there is a double bond. Double bond is always cis in natural fatty acids. CH3 (CH2)6 CH2 CH2 (CH2)6 COOH 18 11 8 1 C C 10 9 H H COOH Oleic acid 18:1 n-9(cis) or 18:1 (Δ9) Chemical formula Elaidic acid • C18H34O2 18:1 (9trans) • C17H33 COOH Unsaturated fatty acids • Dienoic acid: linoleic acid 18:2 (9cis, 12cis) CH3 (CH2)4 CH=CH CH2 CH=CH (CH2)7 COOH Chemical formula C H O 18 32 2 cis C17H31COOH linoleic acid Trienoic acid: linolenic acid 18:3 (9cis, 12cis, 15cis) PolyUnsaturated fatty acids PUFAs • Polyenoic acid (polyunsaturated, tetranoic acid) COOH CH3 Arachidonic acid 20:4 (Δ 5,8,11,14) PUFAs are fatty acids that contain more than one double bond in their backbone UNSATURATED FATTY ACIDS Oleic acid 9 COOH CH -(CH ) -CH=CH-(CH ) -COOH 18:1 ω-9 cis Δ 18 3 2 7 2 7 9 CH -(CH ) -CH=CH-(CH ) -COOH Elaidic acid 18 3 2 7 2 7 18:1 ω-9 trans Δ9 COOH 9 12 9 CH3-(CH2)4-(CH=CH-CH2)2-(CH2)6-COOH Linoleic acid (LA) COOH 9,12 18:2 ω-6 cis Δ 18 12 9 6 CH3-(CH2)4-(CH=CH-CH2)3-(CH2)3-COOH γ-Linolenic acid (GLA) 6,9,12 18:3 ω-6 cis Δ 18 COOH CH3-CH2-(CH=CH-CH2)3-(CH2)6-COOH α-Linolenic (ALA) 9,12,15 COOH 18:3 ω-3 cis Δ 18 9 14 11 8 5 CH3-(CH2)4-(CH=CH-CH2)4-(CH2)2-COOH Arachidonic acid COOH 5,8,11,14 20:4 ω-6 cis Δ 20 17 14 11 8 5 CH -CH -(CH=CH-CH ) -(CH ) -COOH Eicosapentaenoic acid 20 COOH 3 2 2 5 2 2 (EPA) 20:5 ω−3 cis Δ 5,8,11,14,17 19 7 4 CH -CH -(CH=CH-CH ) -CH -COOH Docosahexaenoic acid 22 16 13 10 3 2 2 6 2 (DHA) COOH 22:6 ω−3 cis Δ 4,7,10,13,16,19 Comparison of melting points Melting Points of Saturated vs.
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