Lipids Lecture PDF

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Baghdad College of Pharmacy

Bader S. Alabdullah

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lipids organic chemistry biology science

Summary

This lecture discusses lipids, a diverse group of organic compounds. It covers various types of lipids (fats, oils, waxes), their properties, and their roles in plants and animals. The lecture also details the extraction methods and applications of different types of lipids in pharmaceuticals and industry.

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10/17/2024 Lipids Bader S. Alabdullah Lipids Lipids are a diverse group of organic compounds that are soluble in nonpolar solvents and insoluble in water Chemically, they are esters of long-chain fatty acids and alcoho...

10/17/2024 Lipids Bader S. Alabdullah Lipids Lipids are a diverse group of organic compounds that are soluble in nonpolar solvents and insoluble in water Chemically, they are esters of long-chain fatty acids and alcohols or closely related derivatives The most common types of lipids include fats, oils, and waxes The key distinction between these forms is their state at room temperature: fats are solid oils are liquid waxes are generally solid cetyl alcohol 10/17/2024 Bader S. Alabdullah 2 1 10/17/2024 Lipids (cont.) Lipids play a crucial role in both plants and animals, energy storage In plants, they are most commonly found in seeds In animals lipids accumulate in adipose tissue insulation, protection, and serve as essential components of cell membranes 10/17/2024 Bader S. Alabdullah 3 Fixed Oils and Fats The glycerides of fatty acids Derived either from plant or animal sources They are mixtures of different triglycerides Three fatty acid molecules bound to one glycerol molecule The nature of the fatty acids presents in these triglycerides determines the physical properties of the lipid Saturated or unsaturated Solid or liquid 10/17/2024 Bader S. Alabdullah 4 2 10/17/2024 Fixed Oils and Fats (Cont.) 2 2 10/17/2024 Bader S. Alabdullah 5 Vegetable Oils Vegetable oils are primarily liquid at room temperature High content of unsaturated fatty acids They are extracted through expression (pressing) methods Cold-pressed Higher quality Hot-pressed Higher quantity 10/17/2024 Bader S. Alabdullah 6 3 10/17/2024 Vegetable Oils (cont.) 1. Olive Oil: Derived from the ripe fruit of the Olea europaea, Olive oil is primarily composed of oleic acid, with smaller amounts of linoleic and palmitic acids. It is widely used as a salad oil, in cooking, and in pharmaceuticals for its emollient and mild laxative properties 10/17/2024 Bader S. Alabdullah 7 Vegetable Oils (cont.) 2. Peanut Oil: Also known as arachis oil peanut oil is extracted from the seeds of Arachis hypogaea It is high in oleic acid and linoleic acid It is suitable for cooking and as a solvent for intramuscular injections 10/17/2024 Bader S. Alabdullah 8 4 10/17/2024 Vegetable Oils (cont.) 3. Coconut Oil: Extracted from the seed kernels of Cocos nucifera Coconut oil is a solid at room temperature Due to its high content of saturated fatty acids, particularly lauric and myristic acids It is extensively used in the cosmetic industry for soaps and shampoos In medicine, it is used in formulations for patients with malabsorption issues, Easily digestible 10/17/2024 Bader S. Alabdullah 9 Vegetable Oils (cont.) 4. Soybean Oil: Rich in linoleic acid soybean oil is used in parenteral nutrition Such as in intravenous lipid emulsions It also serves as a source of lecithin A phospholipid involved in lipid metabolism regulation 10/17/2024 Bader S. Alabdullah 10 5 10/17/2024 Animal Fats Animal fats are typically solid at room temperature Due to their higher content of saturated fatty acids They are often separated from other tissues by rendering A process that involves heating the fat to liquefy it and allowing it to rise to the surface 10/17/2024 Bader S. Alabdullah 11 Animal Fats (Cont.) 1. Lard: Obtained from pigs Used in cooking and baking It has a high content of saturated fatty acids Making it solid at room temperature 10/17/2024 Bader S. Alabdullah 12 6 10/17/2024 Animal Fats (Cont.) 2. Tallow: Extracted from beef or mutton fat, It is used in the production of soap and candles, as well as in the culinary world 10/17/2024 Bader S. Alabdullah 13 Chemical Composition of Lipids The chemical composition of lipids largely determines their physical properties and biological functions The fatty acids in lipids can be classified as saturated or unsaturated Saturated fatty acids have no double bonds between the carbon atoms Which allows them to pack closely together Making them solid at room temperature Unsaturated fatty acids contain one or more double bonds Which introduce kinks in the fatty acid chains Preventing them from packing tightly and thus remaining liquid 10/17/2024 Bader S. Alabdullah 14 7 10/17/2024 Chemical Composition of Lipids (Cont.) Palmitic Acid: A saturated fatty acid found in both plant and animal lipids Stearic Acid: Another saturated fatty acid commonly found in animal fats Oleic Acid: A monounsaturated fatty acid that is the main component of olive oil Linoleic Acid: A polyunsaturated fatty acid that is essential for human health found in high concentrations in vegetable oils like soybean and sunflower oil 10/17/2024 Bader S. Alabdullah 15 Chemical Composition of Lipids (Cont.) Caproic CH3(CH2)4COOH Caprylic CH3(CH2)6COOH Capric CH3(CH2)8COOH Lauric CH3(CH2)10COOH Myristic CH3(CH2)12COOH Palmitic CH3(CH2)14COOH Stearic CH3(CH2)16COOH Arachidic CH3(CH2)18COOH Oleic CH3(CH2)7CH=CH(CH2)7COOH Linoleic CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH Linolenic CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7COOH Ricinoleic CH3(CH2)3CHOHCH2CH=CH(CH2)7COOH 10/17/2024 Bader S. Alabdullah 16 8 10/17/2024 Chemical Composition of Lipids (Cont.) Phospholipids Essential components of cell membranes, and Sterols like cholesterol Play a role in maintaining membrane fluidity and Serve as precursors to important biological molecules such as hormones 10/17/2024 Bader S. Alabdullah 17 Biosynthesis of Lipids Lipid biosynthesis is a complex process that occurs in living organisms It was believed that lipids were synthesized by reversing the reactions that degrade them Biosynthetic studies have shown that lipid formation involves distinct pathways and enzymes 10/17/2024 Bader S. Alabdullah 18 9 10/17/2024 Biosynthesis of Lipids (Cont.) The biosynthesis of fatty acids begins with the formation of acetyl-CoA Which reacts with carbon dioxide to form malonyl-CoA This molecule then undergoes a series of condensation, reduction, and dehydration reactions to extend the fatty acid chain by two carbon atoms at a time This process continues until the fatty acid reaches its final length The glycerol backbone used in lipid synthesis is derived from glycerophosphate Which reacts with fatty acyl-CoA molecules to form triglycerides 10/17/2024 Bader S. Alabdullah 19 Biosynthesis of Lipids (Cont.) 10/17/2024 Bader S. Alabdullah 20 10 10/17/2024 Biosynthesis of Lipids (Cont.) The synthesis of unsaturated fatty acids involves the introduction of double bonds by desaturase enzymes Hydroxylated fatty acids are produced through the action of hydroxylases 10/17/2024 Bader S. Alabdullah 21 Pharmaceutical Applications of Lipids Lipids have a wide range of applications in pharmaceuticals They are used as Emollients Vehicles Active ingredients 10/17/2024 Bader S. Alabdullah 22 11 10/17/2024 Pharmaceutical Applications of Lipids (Cont.) 1. Castor Oil: Known for its strong cathartic properties Castor oil is used to induce bowel movements Its main active component is ricinoleic acid 10/17/2024 Bader S. Alabdullah 23 Pharmaceutical Applications of Lipids (Cont.) 2. Lanolin: Derived from the wool of sheep Lanolin is widely used in skin care products for its emollient properties It has a high capacity to absorb water Making it an excellent base for ointments and creams 10/17/2024 Bader S. Alabdullah 24 12 10/17/2024 Pharmaceutical Applications of Lipids (Cont.) 3. Olive Oil: Olive oil is used in pharmaceuticals As a mild laxative and As a base for liniments and ointments The formulation of certain parenteral nutrition products 10/17/2024 Bader S. Alabdullah 25 Pharmaceutical Applications of Lipids (Cont.) 4. Prostaglandins: Prostaglandins play critical roles in various physiological processes Prostaglandin E2 (PGE2) is used to induce labor by stimulating uterine contractions Prostaglandin F2α (PGF2α) is used in the termination of pregnancies 10/17/2024 Bader S. Alabdullah 26 13 10/17/2024 Pharmaceutical Applications of Lipids (Cont.) 4. Liposomes: lipid-based drug delivery systems These are vesicles composed of phospholipid bilayers Can encapsulate drugs Improving their solubility, stability, and bioavailability 10/17/2024 Bader S. Alabdullah 27 Industrial and Nutritional Uses of Lipids In industry, lipids serve as key ingredients in the production of soaps, cosmetics, and paints. The saponification of fats and oils produces soap A process that involves the reaction of a triglyceride with a strong base to form glycerol and fatty acid salts (soap) 10/17/2024 Bader S. Alabdullah 28 14 10/17/2024 Industrial and Nutritional Uses of Lipids (Cont.) Hydrogenated oils are used in food products like margarine and shortening The process of hydrogenation involves adding hydrogen to unsaturated fats to convert them into saturated fats Increases their melting point and extends their shelf life 10/17/2024 Bader S. Alabdullah 29 Industrial and Nutritional Uses of Lipids (Cont.) Lipids are also important in nutrition They provide a concentrated source of energy They are an essential part of the human diet Calories Fat-soluble vitamins (A, D, E, and K) Essential fatty acids like linoleic and alpha-linolenic acids 10/17/2024 Bader S. Alabdullah 30 15 10/17/2024 Waxes Waxes are another important class of lipids They differ from oils and fats in that they contain long-chain alcohols instead of glycerol Waxes are found in both plants and animals Serve various protective functions Preventing water loss in plants Providing structural integrity to animal structures 10/17/2024 Bader S. Alabdullah 31 Waxes (Cont.) 1. Beeswax: Produced by honeybees Used in cosmetics, candles, and pharmaceuticals Serves as a thickening agent in ointments and creams and Provides a protective barrier on the skin 10/17/2024 Bader S. Alabdullah 32 16 10/17/2024 Waxes (Cont.) 2. Carnauba Wax: Extracted from the leaves of the carnauba palm This wax is harder than beeswax and is Used in products like polishes, coatings, and cosmetics 10/17/2024 Bader S. Alabdullah 33 Waxes (Cont.) 3. Jojoba Oil: Technically a liquid wax Used in cosmetics and skin care products for its emollient properties It is a stable, non-greasy oil Closely resembles the natural oils produced by human skin 10/17/2024 Bader S. Alabdullah 34 17 10/17/2024 Specialty Lipid Products 1. Hydrogenated Vegetable Oil: Used as a tablet lubricant Consists mainly of the triglycerides of stearic and palmitic acids Its solid form at room temperature makes it useful in products where stability is key 10/17/2024 Bader S. Alabdullah 35 Specialty Lipid Products (Cont.) 2. Synthetic Spermaceti: Originally derived from the sperm whale Synthetic alternatives have been developed Used in cosmetics and pharmaceuticals for their emollient properties 10/17/2024 Bader S. Alabdullah 36 18 10/17/2024 Fatty Acids and Their Derivatives Stearic Acid: Used as an emollient and tablet lubricant Stearic acid is a common ingredient in cosmetic formulations Its salts, such as calcium stearate and magnesium stearate, are widely used as lubricants in tablet manufacturing 10/17/2024 Bader S. Alabdullah 37 Fatty Acids and Their Derivatives (Cont.) Oleic Acid: A monounsaturated fatty acid found in high concentrations in olive oil Oleic acid is used as an emollient and emulsifying agent Ethyl oleate is used as a pharmaceutic vehicle for injections 10/17/2024 Bader S. Alabdullah 38 19 10/17/2024 Fatty Acids and Their Derivatives (Cont.) Linoleic and Linolenic Acids: Polyunsaturated fatty acids Essential for human nutrition Often included in dietary supplements Support healthy skin, hair, and overall cellular function 10/17/2024 Bader S. Alabdullah 39 10/17/2024 Bader S. Alabdullah 40 20

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