Lipids Chemistry PDF

Definition Classification Biological importance Definition Organic substances relatively insoluble in water but soluble in organic solvents like chloroform, ether and benzene Simple lipid Complex lipid Derived lipids  They are esters of FA with various alcohols...

Definition Classification Biological importance Definition Organic substances relatively insoluble in water but soluble in organic solvents like chloroform, ether and benzene Simple lipid Complex lipid Derived lipids  They are esters of FA with various alcohols Neutral fats or oils Waxes Alcohol is other than Alcohol is GLYCEROL glycerol Esters of FA with alcohol GLYCEROL Uncharged Esters of FA with higher molecular EXAMPLES weight ✓ Lanolin monohydric ✓ Beeswax alcohols ✓ Whale sperm oil  COMPLEX LIPIDS Subclassified according to the type of prosthetic group Phospholipids Glycolipids Lipoproteins  PHOSPHOLIPIDS FA + ALCOHOL + PHOSPHORIC ACID They frequently have nitrogen containing bases  PHOSPHOLIPIDS Phospholipids may be classified on the basis of the type of alcohol present A. Glycerophospholipids B. Spingophospholipids ✓ Phosphatidylcholine ✓ Phosphatidyl ethanolamine ✓ Phosphatidyl serine ✓ Phosphatidyl inositol ✓ Spingomyelins ✓ Plasmalogens ✓ Cardiolipins SPHINGOPHOSPHOLIPID  Functions of phospholipids In association with proteins phospholipids form the structural components of membranes and regulate membrane permeability. Phospholipids participate in the absorption of fat from the intestine. Essential for the synthesis of different lipoproteins, and thus participate in the transport of lipids. Accumulation of fat in liver (fatty liver) can be prevented by phospholipids, hence they are regarded as lipotropic factors. Arachidonic acid, an unsaturated fatty acid liberated from phospholipids, serves as a precursor for the synthesis of eicosanoids (prostaglandins, prostacyclins, thromboxanes etc.).  Functions of phospholipids Phospholipids participate in the reverse cholesterol transport and thus help in the removal of cholesterol from the body. Phospholipids act as surfactants (agent lowering surface tension). Cephalins,an important group of phospholipids participatin blood clotting. Phospholipids( phosphatidyl inositoal ) involved in signal transmission across membranes.  GLYCOLIPIDS FA + ALCOHOL[SPINGOSINE] +CARBOHYDRATE WITH NITROGEN BASE Example ✓Cerebrosides ✓Gangliosides GLYCOLIPIDS  LIPOPROTEINS ✓Chylomicrons Lipid with ✓Very low density lipoprotein (VLDL) prosthetic ✓Low density lipoprotein (LDL) group PROTEIN ✓High density lipoprotein (HDL)  DERIVED LIPIDS These are the derivatives obtained on the hydrolysis of group 1 and group 2 lipids which possess the characteristics of lipids. Example Vitamin A Fatty acids Steroids Cholesterol and D  FUNCTIONS OF LIPIDS Structural Precursor of Act as Protection of Storage form component many steroid thermal internal of energy of cell hormones, insulator organs membrane. vitamin D  FUNCTIONS OF LIPIDS Fats serve as Helps in Acts as Lipoproteins surfactants Improve absorption electric transporting by reducing taste and of fat soluble insulators in lipids surface palatability. vitamins neurons. tension.  Fatty acids Fatty acids are naturally occurring carboxylic acids with an unbranched carbon chain and an even number of carbon atoms. The pathway by which fatty acids are biosynthesized they almost always contain an even number of carbon atoms. Long-chain fatty acids (12 to 26 carbon atoms) are found in meats and fish medium-chain fatty acids (6 to 10 carbon atoms) and short-chain fatty acids (fewer than 6 carbon atoms) occur primarily in dairy products. There are saturated and unsaturated Fatty acids.  Saturated fatty acid : Fatty acid chains that contain only carbon-carbon single bonds are referred to as saturated (Palmitic acid) Unsaturated fatty acid : Those molecules that contain one or more double bonds are said to be unsaturated. There are mono- and polyunsaturated fatty acids (Oleic acid) Prostaglandins are derivative of fatty polyunsaturated acids What are Essential Fatty Acids (EPA)? There are TWO essential fatty acids. Essential means you NEED to get them from the diet because the body cannot manufacture them. -linolenic acid (LNA or ALA): an omega-3 fatty acid 1 ALA COH 1 3 15 12 9 -Linolenic acid O Linoleic acid (LA): an omega-6 fatty acid found abundantly in soy oil, sunflower seeds, pumpkin seeds, sesame seeds, corn oil, and in most nuts. 1 COH 12 9 O Linoleic acid cis-9,12-Octadecadienoic aicd, 18:2(9,12) Functions of EFA Essential fatty acids are required for the membrane structure and function. Transport of cholesterol. Formation of lipoproteins. Prevention of fatty liver etc. They are also needed for the synthesis of another important group of compounds, namely eicosanoids.  Rancidity Rancidity: Rancidity is the term used to represent the deterioration of fats and oils resulting in an unpleasant taste. Fats containing unsaturated fatty acids are more susceptible to rancidity. Rancidity occurs when fats and oils are exposed to air, moisture, light, bacteria etc. Hydrolytic rancidity occurs due to partial hydrolysis of triacylglycerols by bacterial enzymes. Oxidative rancidity is due to oxidation of unsaturated fatty acids. This results in the formation of unpleasant products such as dicarboxylic acids, aldehydes, ketones etc. Rancid fats and oils are unsuitable for human consumption.  Test to Check Purity of Fats and Oils Acid number:- It is the number of milligrams of potassium hydroxide required to completely neutralize the free fatty acids present in 1 g of the oil or fat. In normal circumstances refined oils should be free from any free fatty acids. Oils, on decomposition due to chemical or bacterial contamination-yield free fatty acids. Therefore, oils with increased acid number are unsafe for human consumption  Test to Check Purity of Fats and Oils Saponification number:- It is defined as the mg (number) of KOH required to hydrolyze (saponify) one gram of fat or oil. Saponification number is a measure of the average molecular size of the fatty acids present The value is higher for fats containing short chain fatty acids. Human fat : 195-200 Butter :230-240 Coconut oil : 250-260  Test to Check Purity of Fats and Oils Iodine number:- lt is defined as the grams (number) of iodine absorbed by 100 g of fat or oil. Iodine number is useful to know the relative unsaturation of fats, and is directly proportional to the content of unsaturated fatty acids. Thus lower is the iodine number, less is the degree of unsaturation. Determination of iodine number will help to know the degree of adulteration of a given oil.  Test to Check Purity of Fats and Oils Reichert-Meissl (RM) number:- lt is defined as the number of ml 0.1 N KOH required to completely neutralize the soluble volatile fatty acids distilled from 5 g fat. RM number is useful in testing the purity of butter since it contains a good concentration of volatile fatty acids( butyric acid, caproic acid and caprylic acid). Butter has a RM number in the range 25-30, while it is less than 1 for most other edible oils. Thus any adulteration of butter can be easily tested by this sensitive RM number.  Chemical Reactions of Fatty Acids Esterification reacts fatty acids with alcohols to form esters and water  Fatty Acid Hydrolysis Acid Hydrolysis reverses esterification. Fatty acids are produced from esters  Saponification Saponification is the base-catalyzed hydrolysis of an ester Products of the reaction are – An alcohol – An ionized salt which is a soap Soaps have a long uncharged hydrocarbon tail Also have a negatively charged carboxylate group at end Form micelles that dissolve oil and dirt particles Thank You