fatty acids.pptx
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This document discusses fatty acids, which are carboxylic acids and key building blocks for lipids. Fatty acids can be saturated or unsaturated depending on whether they contain single or double carbon bonds. They are classified based on chain length and the number and position of double bonds. Unsaturated fatty acids have lower melting points than saturated fatty acids. Essential fatty acids like omega-3 and omega-6 must be obtained through diet as the human body cannot synthesize them. Fatty acids play important structural and physiological roles.
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Complex lipids include phospholipids, glycolipids, and lipoproteins. Phospholipids are the major components of cell membranes and contain a phosphate group. The most abundant phospholipid, phosphatidylcholine or lecithin, plays structural and metabolic roles. Glycolipids consist of cerebrosides found in the brain and gangliosides found in gray matter that serve as receptor sites. Deficiencies in the enzymes that break down glycolipids can cause lipid storage diseases.
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fatty acids.pptx
- 1. 13-10-2011
- 2. FATTY ACIDS • Fatty acids are carboxylic acids with hydrocarbon side chain • Simplest form of lipids • Key building blocks for lipids • Chains of carbon atoms with a carboxyl group at one end, and a methyl group at the other • May be “free” or attached to another compound • Determine the characteristics of the fat
- 4. • Omega 3 • Omega 6 • Omega 9
- 5. Classification of fatty acids Depending on total number of carbon atoms 1. Even chain fatty acids: • having carbon atoms 2,4,6 & series • exapmle: Acetic acid Butyric acid Caproic acid Palmitic acid 2. Odd chain fatty acids: • having carbon atoms 3,5,7 etc • Seen in microbial cell walls & also present in milk • Example: Propanoic Valeric
- 6. Cont.. Depending on the length of hydrocarbon chain • Short chain = 2-6 carbons • Medium chain = 8-14 carbons • Long chain = 16 & above, usually up to 24 carbons
- 7. Depending the nature of hydrocarbon chain • Saturated fatty acids • Unsaturated fatty acids • Branched chain fatty acids (e.g. isovaleric acid) • Hydroxy fatty acids (e.g. cerebronic acid)
- 8. • If all the carbon atoms in the chain are joined with single bonds, and the remaining bonds are attached to hydrogen • Long-chain saturated fatty acids stack tightly and form solids at room temperature • Short-chain saturated fatty acids are also liquid at room temperature SATURATED FATTY ACID
- 9. Saturated Fatty Acids Completely Unbranched and saturated with no double bonds
- 11. UNSATURATED FATTY ACID • If adjoining carbons are joined by double bonds • One double bond = monounsaturated fatty acid • Two or more double bonds = poly- unsaturated fatty acid • Monounsaturated and polyunsaturated fatty acids don’t stack compactly and are liquid at room temperature
- 13. Nomenclature of Fatty Acids COOH 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 Number of Double Bonds Position of Double Bonds Carbon Chain Length 18:3 ( 9, 12, 15) The most commonly occurring fatty acids have even number of carbon atoms in an un-branched chain of12-24 carbons
- 14. CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-COOH 12 11 10 9 8 7 6 5 4 3 2 1 or CH3 (CH2)10 –COOH Dodecanoic acid (Lauric) 14:0 tetradecanoic acid 16:0 Hexadecanoic acid 20:0 Eicosanoic acid 22:0 Docosanoic acid 24:0 Tetracosanoic acid No double bonds for eg in 18:0, Octadecanoic acid If one double bond then acid Octadecenoic acid If two double bonds then Octadecadienoic acid If three double bonds Octadecatrienoic acid. Systematic names are based on IUPAC nomenclature:
- 15. General Patterns of Double Bonds The most common positions for double bonds are Δ9, Δ12, and Δ15. The double bonds of polyunsaturated fatty acids are separated by methyl group: -CH=CH-CH2-CH=CH- In almost all the naturally occurring unsaturated fatty acids, the double bonds are in Cis- configuration
- 16. TWO TYPES OF BOND FORMATION: • CIS - hydrogens on the carbons joined by a double bond are on the same side = the carbon chain is bent • TRANS – hydrogens on the carbons joined by a double bond are on the opposite side = the carbon chain is straighter
- 18. Physical Properties of Fatty Acids The physical properties of fatty acids are largely determined by the length and degree of unsaturation of the hydrocarbon chain. The longer the chain and the fewer the double bonds, the lower is the solubility in water, and higher is the melting point. • Addition of double bonds decreases the melting point whereas, increasing the chain length increases the melting point. For example; 4:0 MP -7.9 C, 12:0 MP 44.2 C, 16:0 MP 62.7 C, 18:1 MP 10.5 C, 18:2 MP -5.0 C, 18:3 MP -11 C.
- 19. Chemical Properties of fatty acids • Hydrogenation • Halogenation • Salt formation • Ester formation
- 20. Isomerism • A double bond in Fatty acid chain permits two types of geometrical isomers, cis and trans. • Cis isomers have a curved configuration. • Trans isomers have a linear configuration. • Due to curve configuration cis unsaturated fatty acids have a lower melting point as compared to there trans counterpart. • Most of the natural unsaturated fatty acids have cis double bonds.
- 21. The Packing of Fatty Acids
- 22. Essential fatty acids • The fatty acids that can not be synthesized by the body, & therefore, should be supplied in the diet is known as essential fatty acids • Chemically, they are polyunsaturated • Example: - Linoleic acid (18:2,9,12) - Linolenic acid (18:3,9,12,15) - Arachidonic acid (20:4,5,8,11,14)
- 23. Function of EFA • Structural elements of tissue • Structural elements of gonads • Synthesis of prostaglandins and other compounds • Structural components of mitochondrial membrane • Serum level of cholesterol • Effect on clotting time • Effect on fibrinolytic activity • Role of EFA in fatty liver • Role in vision