LIPIDS: Fixed Oils, Fats, and Waxes

• Fixed oils, fats, and waxes: Esters of long-chain fatty acids and alcohols, or closely related derivatives

• Saturated Fatty Acids:

• Unsaturated Fatty Acids:

• Fixed Oils:

- Long Chain Fatty Acids: Long chain FA

- Glycerol: glycerol

- From: From vegetables

- Room Temperature: Liquid at room temperature

- Exceptions: Solid FO - myristica

- Use: Use: storage

• Fats:

- Long Chain Fatty Acids: Long chain FA + glycerol

- Glycerol: glycerol

- From: From animals

- Room Temperature: Semi-solid or solid at room temp.

- Exceptions: Exceptions: LF: cod liver oil

- Use: Use: storage

• Waxes:

- Long Chain Fatty Acids: Long chain FA

- Glycerol: HMW alcohol

- From: (cetyl and stearyl alcohol)

- Room Temperature: solid

- Exceptions: Exceptions: LW: jojoba oil

- Use: Use: protectant

• Fats and oils are made from two kinds of molecules:

- Glycerol

- 3 fatty acids joined by dehydration synthesis

• Fatty Acids:

- Saturated Fatty Acids

- Butyric acid: Butter fat

- Lauric acid: Coconut oil

- Myristic acid: Palm oil

- Palmitic acid: Arachis oil, sesame oil

- Stearic acid: Arachis oil

- Arachidic oil: Mustard oil

- Unsaturated Fatty Acids

- Linolenic acid: Linseed oil

- Linoleic acid: Sesame oil, sunflower oil

- Arachidonic acid: Arachis oil

- Oleic acid: Safflower oil, corn oil

METHODS OF EXTRACTION

• Expression:

- Process of mechanically pressing of liquid out of liquid containing solids

- Most widely used for fixed oil

- Types:

- Cold Expression

- Hot Expression

• Rendering:

- Consists of cutting or chopping the fatty tissue into small pieces that are boiled in open vats or cooked in steam digesters

- Most widely used for fats

• Extraction by Solvents:

- Process in which compounds are separated on their solubility

- Hexane is the most used solvent for extraction

- Most widely used for fats

USP TEST FOR LIPIDS

• Acid Value or Acid Number:

- Refers to the number of mg of potassium hydroxide required to neutralize the free acids in 1 g of the oil.

- High acid values arise in rancidified oils.

• Saponification Value/Kottstorfer:

- The hydrolysis reaction of lipids can be used to determine the saponification value of the oil and is expressed as the number of mg of potassium hydroxide required to neutralize the free acids in, and to hydrolyze the esters in, 1 g of the substance.

• Ester Value:

- Is the difference between the saponification and acid values.

• Iodine Value:

- Gives a measure of the unsaturation of the oil.

- The mass of iodine in grams that is consumed by 100 g of fats or oil.

• Acetyl Value:

- The number of milligrams of potassium hydroxide required to neutralize the acetic acid freed by the hydrolysis of the acetylated fat or other substance.

- It is expressed as the number of milligrams of potassium hydroxide required to neutralize the acid combined by acylation of the sample.

- Castor oil – minimum value 150.

LIPID FUNCTIONS

• For Plants:

- Serves as food or energy storage

- Pharmaceutical applications: Emollient, vehicles for emulsions

- In the arts and Industry: Manufacture of soaps, paints, varnishes

- Therapeutic values: As antifungal, dietary supplements, sclerosing agents

TYPES OF LIPIDS

• Fixed Oils:

- Only substances obtained mainly from plant sources.

- Mixtures of glyceryl esters of high MW fatty acids.

- Unsaturated fats.

- Liquid at room temperature except for cocoa butter.

• Physical Characteristics of Fixed Oils:

- Cannot be distilled.

- Leaves a permanent, translucent stain on filter paper.

- Specific gravity < 1.

- All insoluble in water.

- Most develop a rancid odor.

- All have characteristic odor.

- Varying viscosities.

• Classification of Fixed Oils:

- Drying Oil: When exposed to air, undergo oxidation and form tough and hard film. These are usually used in paints and varnishes. For example; Linseed oil.

- Non-Drying Oil: These oils neither undergo oxidation nor form tough and hard film. For example; Olive oil.

- Semi-Drying Oil: When exposed to air, undergo little bit oxidation and form tough and thin film. For example; Cotton seed oil.

FIXED OIL SOURCES

• Castor Oil/Castor Bean:

- Source: Ripe seed of Riccinus communis

- Family: Euphorbiaceae

- Constituent: Ricin and Ricinoleic acid

- Use: ointment base, plasticizer, wetting agents, lubricating agent, stimulant cathartic

• Olive Oil/Sweet Oil:

- Source: Ripe fruit of Olea europaea

- Family: Oleaceae

- Constituent: 75% oleic acid, 10% palmitic acid and 9% linoleic acid

- Use: setting retardant for dental cements, soaps, plasters, emollient, laxative and liniment

• Peanut Oil:

- Source: Ripe seed of Arachis hypogaea

- Family: Leguminosae

- Constituent: 20% protein (thiamine), 50-65% oleic acid, 18-30% linoleic acid, 8 – 10% stearic acid, arachidic, beheric and lignoceric acid

- Use: vehicle for intramuscular medication

• Soybean Oil:

- Source: Ripe seed of Glycine soja Siebold et Zaccarini

- Family: Leguminosae

- Constituent: 50% linoleic acid, 30% oleic acid, 14% palmitic and stearic acid and 7% linolenic acid

- Use: Food for diabetic patients and source of lecithin in parenteral nutrients

• Cotton Seed Oil:

- Source: Ripe seed of cultivated plants of various varieties of Gossypium hirsutum, Linn

- Family: Malvaceae

- Constituent: 4% linoleic acid, 30% oleic acid, 20% myristic acid 1% stearic acid and arachidic acid

- Use: solvent for injections, substitutes for lard and in soaps

• Sesame Seed Oil/Teel/Benne:

- Source: Seed of one or more cultivated varieties of Sesamum indicum Linn.

- Family: Pedaliaceae

- Constituent: 43% linoleic acid, 43% oleic acid, 9% palmitic acid 4% stearic

- Use: solvent for IM injections, nutritive, laxatives, demulcent and emollient

• Almond Oil/Sweet Almond/Bitter Almond:

- Source: ripe seeds different varieties of Prunus amygdalus Batsch

- Family: Rosaceae

- Constituent: 77% oleic acid, 17% linoleic acid, 5% palmitic acid 1% Myristic

- Use: flavoring agent (volatile oil) and emollient (cosmetics)

• Persic Oil/Apricot Kernel Oil/Peach Kernel Oil:

- Source: kernels of varieties of Prunus armeniaca Linn. (Apricot kernel oil) or Prunus persica Siebold et Zuccarini

- Family: Rosaceae

- Use: Same as Almond oil)

• Coconut Oil:

- Source: Dried solid part of endosperm of Cocos nucifera Linn

- Family: Palmae

- Constituent: 50% Lauric acid and 20% Myristic acid

- Use: Balanced dietary supplements

• Corn Oil:

- Source: Embryo of Zea mays Linn

- Family: Poaceae

- Constituent: 50% linoleic, 37% oleic acid, 10% palmitic acid 3% Stearic acid

- Use: Balanced dietary supplements

• Corn Oil:

- Source: Embryo of Zea mays Linn

- Family: Poaceae

- Constituent: 50% linoleic, 37% oleic acid, 10% palmitic acid 3% Stearic acid

- Use: Solvent for IM injection, solvent for irradiated ergosterol and balanced dietary supplements

• Safflower Oil:

- Source: seeds of Carthamus tinctoria Linn.

- Family: Asteraceae

- Constituent: 75% linoleic and 18% oleic acid

- Use: cooking oil, salad oil, margarine, mayonnaise, paints and varnishes

• Sunflower Oil:

- Source: The seeds of cultivated varieties of Helianthus annuus Linn.

- Family: Asteraceae

- Constituent: 44 - 77% linoleic acid and 23% oleic acid

- Use: Alternative to corn oil and safflower for culinary purpose and dietary supplement ingredient

• Ethiodized Oil:

- Source: Papaver somniferum

- Family: Papaveraceae

- Constituent: 35.2% to organically combined iodine

- Use: Radiopaque and is used as a diagnostic aid in hysterosalpingography and lymphography

• LIPIO FLUIDE

- LIPIODOL ULTRA FLUIDE

- 10ml

- NhaThuocLP.com

• Fats:

- Oily substances obtained mainly from animal sources.

- Produced in various organs of animals.

- Saturated fats.

- Solid at room temperature (except for Cod Liver oil).

FATS AND RELATED COMPOUNDS SOURCES

• Theobroma Oil/Cacao Seed/Cacao Beans:

- Source: Roasted seeds of Theobroma cacao

- Family: Sterculiaceae

- Constituent: 35 – 50% fixed oils, 15% starch, 15% Proteins, 1-4% theobromine and 0.070.36% caffeine

- Use: flavoring agent (cocoa syrup) and suppository base

• Lanolin/Hydrous Wool Fat:

- Source: Purified fatlike substance from the wool of the sheep Ovis aries Linn.

- Family: Bovidae

- Constituent: Cholesterol and Isocholesterol

- Use: Water absorbable ointment base and ingredients for cosmetics (cream)

• Anhydrous Lanolin/Wool Fat:

- Lanolin which contains not more than 0.25% water.

- Use: Water absorbable ointment bases and emollient properties

• RANGE PRODUCTS LANOUN

• Cod Liver:

- Source: Fresh livers of Gadus morrhua

- Family: Galidae

- Constituents: EHA and DHA

- Uses: source of Vit. A and D dietary supplement and topical emollients, antirachitic, sclerosing agent

TYPES OF FATTY ACIDS

• Fatty Acids:

- Carboxylic acid with long hydrocarbon chain

- ❑ the hydrocarbon chain 10-30 carbons

- ❑ obtained by the hydrolysis of fats and oils

- Long hydrocarbon chain

- Carboxylic acid group

FATTY ACIDS EXAMPLES

• Saturated Fats

- Formula: CH3(CH2)10СО2H

- Common Name: lauric acid

- Formula: CH3(CH2)12СО2Н

- Common Name: myristic acid

- Formula: CH3(CH2)14СО2Н

- Common Name: palmitic acid

- Formula: CH3(CH2)16СО2H

- Common Name: stearic acid

- Formula: CH3(CH2)18СО2Н

- Common Name: arachidic acid

• Unsaturated Fats

- Formula: СН3(CH7)5CH=CH(CH7)7СО2H

- Common Name: palmitoleic acid

- Formula: CH3(CH7)7CH=CH(CH2)7CO2H

- Common Name: oleic acid

- Formula: CH3(CH7)4CH=CHCH?CH=CH(CH7)7СО2Н

- Common Name: linoleic acid

- Formula: CH3CHZCH=CHCHZCH=CHCHZCH=CH(CH7)7СОЛИ

- Common Name: linolenic acid

- Formula: CH3(CH2)4(CH=CHCH2)4(CH2)2СО2Н

- Common Name: arachidonic acid

FATTY ACID SOURCES

• Stearic Acids:

- Hard, white or faintly yellow soilds or powders, practically insoluble to water

- Stearic Acid

- Pharmaceutical stearic acid: 40% of stearic acid and palmitic acid.

- Purified stearic acid: 90% stearic acid + 96% palmitic acid.

- Use: Emulsion and tablet lubricant

• Oleic Acids:

- Obtained from edible fats and fixed oils.

- By product in the production of stearic acids.

- Use: Emulsion adjunct

- Ethyl oleate: vehicle (less viscous and rapidly absorbs).

- oleyl alcohol: emollient and emulsifying agent.

• Linolenic Acids:

- Polyunsaturated octadecanoic acids.

- Obtained from soybean oil and other.

- Use: dietary supplements

• Undecylenic Acid:

- 10 undecanoic acid.

- Prepared by pyrolysis of ricinoleic acid.

- Use: antifungal (Athlete’s foot)

TYPES OF WAXES

• Waxes:

- Esters of high MW monohydric: alcohols and high MW fatty acids.

- Composed of long chain of fatty acids united with long chain alcohol containing 24 to 36 Carbon atoms (arranged in straight, unbranched chains).

- Found in outer cell walls of epidermal tissue.

WAXES SOURCES

• Synthetic Spermaceti/Cetyl Esters Wax:

- Source: sperm whale Physeter macrocephalus Linn

- Family: Physeteridae

- Constituents: hexadecyl esters of fatty acids

- Uses: emulsifying agent and as stiffening agent in pharmaceutic preparations

• Jojoba Oil:

- Source: liquid wax expressed from seeds of Simmondsia chinensis

- Family: Buxadeceae

- Constituents: 45 -55% Eicosanoic acids: eicosanoids and docosenol

- Uses: Emollient and pharmaceutical necessity

• Beeswax/Yellow Wax:

- Source: Purified wax from the honeycomb of the bee Apis melifera

- Family: Apidae

- Constituents: Myricyl palmitate, myricyl cerotate, hypogaeate, cerotic acid and hydrocarbon

- Bleached/unbleached

- Uses: component of yellow and white ointment, USP; base for cerates and plasters

PROSTAGLANDINS

• Prostaglandins:

- C20 lipid metabolites formed in the body from essential, unsaturated fatty acids of the diet.

- Prostaglandins

• Pharmacological Effects:

- Contraction and relaxation of smooth muscles of female reproductive system and cardiovascular system, intestinal tract and the bronchi.

- Influence gastric secretion and renal function.

PROSTAGLANDINS F2a

• PGF2a/Dinoprost:

- Available as tromethamine salt for use in terminating 2nd trimester pregnancy.

- Stimulates constructions of the uterus oxytoxic agent.

15 METHYLPROSTAGLANDINS F2a

• 15-MethylPGF2a/Carboprost:

- Available as tromethamine salt for use in terminating 2^{nd } trimester pregnancy.

- Stimulates constructions of the uterus oxytoxic agent.

PROSTAGLANDINS E2

• Dinoprostone:

- Uterine stimulant

- Terminates 2nd trimester of pregnancy

- Available as vaginal suppository

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