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- Nomenclature, classifications, - identification and exstraction of lipids - Soap CHAPTER II
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Lipid nomenclature systematic names and common or trivial names
The nomenclature of lipids falls into two main categories: systematic names and common or trivial names by International Union of Biochemistry and Molecular Biology (IUPAC-IUBMB) ( clarification of the use of core structures to simplify systematic naming of some of the more complex lipids provision of systematic names for recently discovered lipid classes.
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Palmitic acid Fatty acids Numerical symbol Structure 'Name'
H3C-(R)-CO2H systematic namesa trivial namesb symbol 16:0 -[CH2]14- Hexadecano- Palmit- Pam Fatty acids
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Numerical symbol Structure Stems of 'Name' H3C-(R)-CO2H systematic namesa trivial namesb symbol 1 10:0 -[CH2]8- Decano- Capr-c Dec 2 12:0 -[CH2]l0- Dodecano- Laur- Lau 3 14:0 -[CH2]12- Tetradecano- Myrist- Myr 4 16:0 -[CH2]14- Hexadecano- Palmit- Pam 5 16:1 -[CH2]5CH=CH[CH2]7- 9-Hexadeceno- Palmitole- DPam 6 18:0 -[CH2]16- Octadecano- Stear- Ste 7 18:1(9) -[CH2]7CH=CH[CH2]7- cis-9-Octadeceno- Ole- Ole 8 18:1(11) -[CH2]5CH=CH[CH2]9- 11-Octadeceno- Vaccen- Vac 9 18:2(9,12) -[CH2]3(CH2CH=CH)2[CH2]7- cis,cis-9,12-Octadecadieno- Linole Lin 10 18:3(9,12,15) -(CH2CH=CH)3[CH2]7- 9,12,15-Octadecatrieno- (9,12,15)-Linolen- aLnn 11 18:3(6,9,12) -[CH2]3(CH2CH=CH)3[CH2]4- 6,9,12-Octadecatrieno- (6,9,12)-Linolen- gLnn 12 18:3(9,11,13) -[CH2]3(CH=CH)3[CH2]7- 9,11,13-Octadecatrieno- Eleostear- eSte 13 20:0 -[CH2]18- Icosano-d Arachid- Ach 14 20:2(8,11) -[CH2]6(CH2CH=CH)2[CH2]6- 8,11-Icosadieno-d D2Ach 15 20:3(5,8,11) -[CH2]6(CH2CH=CH)3[CH2]3- 5,8,11-Icosatrieno-d D3Ach 16 20:4(5,8,11,14) -[CH2]3(CH2CH=CH)4[CH2]3- 5,8,11,14-Icosatetraeno-d Arachidon- D4Ach 17 22:0 -[CH2]20- Docosano- Behen- Beh 18 24:0 -[CH2]22- Tetracosano- Lignocer- Lig 19 24:1 -[CH2]7CH=CH[CH2]13- cis-15-Tetracoseno- Nervon- Ner 20 26:0 [CH2]24- Hexacosano- Cerot- Crt 21 28:0 -[CH2]26- Octacosano- Montan- Mon
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LIPID MAPS abbreviations for glycerolipids
Class Abbreviation Examples Monoradylglycerolipids MG MG(16:0/0:0/0:0) Diradylglycerolipids DG DG(16:0/18:1(9Z)/0:0) Triradylglycerolipids TG TG(16:0/18:1(9Z)/16:0)
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LIPID MAPS abbreviations for glycerophospholipids
Class Abbreviation Examples Glycerophosphocholines PC (LPC for lyso species) PC(P-16:0/18:2(9Z,12Z)) Glycerophosphoethanolamines PE (LPE for lyso species) PE(O-16:0/20:4(5Z,8Z,11Z,14Z)) Glycerophosphoserines PS (LPS for lyso species) PS(16:0/18:1(9Z)) Glycerophosphoglycerols PG (LPG for lyso species) - Glycerophosphates PA (LPA for lyso species) PA(16:0/0:0) or LPA(16:0) Glycerophosphoinositols PI (LPI for lyso species) PI(18:0/18:0) Glycerophosphoinositol monophosphates PIP Glycerophosphoinositol bis-phosphates PIP2 Glycerophosphoinositol tris-phosphates PIP3 Glycerophosphoglycerophosphoglycerols (Cardiolipins) CL CL(1'-[16:0/18:1(11Z)],3'-[16:0/18:1(11Z)]) Glycerophosphoglycerophosphates PGP Glyceropyrophosphates PPA CDP-glycerols CDP-DG Glycosylglycerophospholipids [glycan]-GP Glycerophosphoinositolglycans [glycan]-PI Glycerophosphonocholines PnC Glycerophosphonoethanolamines PnE
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Classification of lipids
Although lipid analyst tend to have a firm understanding of what is meant by the term "lipid", there is no widely-accepted definition. The historical origins of the term ‘lipid’ make interesting reading, and should assist with a definition . The term has evolved via ‘lipine’, ‘lipin’, ‘lipoid’ and ‘lipide’ and was originally used in a more restricted sense. Thus, Bloor in 1920 classified lipoids into three groups, simple lipoids (fats and waxes), compound lipoids (phospholipoids and glycolipoids) and derived lipoids (fatty acids, alcohols and sterols). This classification appears to have been accepted until the 1950s. Only later and rather arbitrarily were compounds such as carotenoids, terpenes and steroidal hormones included in the term
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A. Simple lipid - ester of fatty acids with various alcohols
Bloor’s Classification A. Simple lipid - ester of fatty acids with various alcohols 1. Natural fats and oils (triglycerides) 2. Waxes (a) True waxes: cetyl alcohol esters of fatty acids (b) Cholesterol esters (c) Vitamin A esters (d) Vitamin D esters B.Compound lipid - esters of fatty acids with alcohol plus other groups 1. Phospholipids and spingomyelin: contains phosphoric acid and often a nitrogen base 2. Spingolipids (also include glycolipids and cerebrosides): contains aminoalcohol spingosine, carbohydrate, N-base; glycolipids 3.Sulfolipids : contains sulfate group 4. Lipoproteins : lipids attached to plasma/other proteins 5. Lipopolysaccharides: lipids attached to polysaccharides
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C. Derived lipids – hydrolytic products of A & B with lipid characters
1. Saturated & unsaturated fatty acids 2. Monoglycerides and diglycerides 3. Alcohols (b-carotenoid ring, e.g., vitamin A, certain carotenoids) Walter R. Bloor
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There is no definition of lipid that has been accepted by any international body that recommends standards or comments on nomenclature issues. definition was first put forward in until something better is proposed. It is - Lipids are fatty acids and their derivatives, and substances related biosynthetically or functionally to these compounds. A further useful guide to lipid nomenclature and structures is a paper by Fahy and colleagues, which is available from the Journal of Lipid Research as a free download . It is complemented by a website – LIPID MAPS Saccharolipids [SL] Fatty Acyls [FA] Glycerophospholipids [GP] Sterol Lipids [ST] Prenol Lipids [PR] Glycerolipids [GL] Sphingolipids [SP] Polyketides [PK]
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Identification and and extraction of lipids
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1-Iodine number (or value):
Definition: It is the number of grams of iodine absorbed by 100 grams of fat or oil. Uses: It is a measure for the degree of unsaturation of the fat, as a natural property for it. Unsaturated fatty acids absorb iodine at their double bonds, therefore, as the degree of unsaturation increases iodine number and hence biological value of the fat increase. It is used for identification of the type of fat, detection of adulteration and determining the biological value of fat.
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2-Saponification number (or value):
Definition: It is the number of milligrams of KOH required to completely saponify one gram of fat. Uses: Since each carboxyl group of a fatty acid reacts with one mole of KOH during saponification, therefore, the amount of alkali needed to saponify certain weight of fat depends upon the number of fatty acids present per weight. Thus, fats containing short-chain acids will have more carboxyl groups per gram than long chain fatty acids and consume more alkali, i.e., will have higher saponification number.
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soap In chemistry, soap is a salt of a fatty acid.
Soaps are mainly used as surfactants for washing, bathing, and cleaning, but they are also used in textile spinning and are important components of lubricants.
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Saponifiable and Nonsaponifiable Lipids
Lipids can be considered to be biological molecules which are soluble in organic solvents, such as chloroform/methanol, and are sparingly soluble in aqueous solutions. There are two major classes, saponifiable and nonsaponifiable, based on their reactivity with strong bases. The nonsaponifiable classes include the "fat-soluble" vitamins (A, E) and cholesterol.
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Saponification Saponification is the process that produces soaps from the reaction of lipids and a strong base. The saponifiable lipids contain long chain carboxylic acids, or fatty acids, esterified to a “backbone” molecule, which is either glycerol or sphingosine.
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LIPID EXTRACTION necessary to jump to 1879 when Franz von Soxhlet described the first method based on an automatic solvent extraction (diethyl ether) for milk lipids The Soxhlet extractor
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EXTRACTION WITH SPECIFIC INSTRUMENTS
MICROWAVE OVEN SUPERCRITICAL FLUID EXTRACTION PRESSURIZED FLUID EXTRACTION SOXHLET-TYPE EXTRACTION ULTRASOUND-ASSISTED EXTRACTION ROBOT AUTOMATED EXTRACTION
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the next: COMMERCIAL USES of lipids
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