Fatty acids and glycerides:
Gespeichert in:
| Format: | Buch |
|---|---|
| Sprache: | English |
| Veröffentlicht: |
New York u. a.
Plenum Pr.
1979
|
| Ausgabe: | 2. print. |
| Schriftenreihe: | Handbook of lipid research.
1. |
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XVII, 469 S. graph. Darst. |
| ISBN: | 0306335816 |
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| 336 | |b txt |2 rdacontent | ||
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| 338 | |b nc |2 rdacarrier | ||
| 490 | 1 | |a Handbook of lipid research. |v 1. | |
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| 650 | 7 | |a Glycérides |2 ram | |
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| adam_text | Contents
Chapter 1
Separation and Determination of Structure of Fatty Adds
Amis Kuksis
1.1. Introduction 1
1.2. Preparation and Isolation of Fatty Acids 2
1.2.1. Generation of Free Acids 2
1.2.2. Preparation of Derivatives 4
1.2.3. Transesterification of Bound Acids 6
1.3. Preliminary Fractionation of Fatty Acids 7
1.3.1. Conventional TLC 7
1.3.2. Argentation TLC 9
1.3.3. Other Methods 11
1.4. Identification of Fatty Acids by Gas Liquid
Chromatography 12
1.4.1. Short Chain Acids 13
1.4.2. Saturated Normal and Branched Chain
and Cyclic Acids 14
1.4.3. Ethylenic Acids 21
1.4.4. Acetylenic Acids . . . 30
1.4.5. Oxygenated Acids 36
1.5. Identification of Fatty Acids by Gas
Chromatography/Mass Spectrometry 40
1.5.1. Saturated Normal and Branched Chain
and Cyclic Acids 40
1.5.2. Ethylenic and Acetylenic Acids 43
1.5.3. Oxygenated Acids 45
1.5.4. Stable Isotope Labeled Fatty Acids 48
1.6. Ancillary Methods of Fatty Acid Identification 50
1.6.1. Chemical Methods 50
1.6.2. Spectrometric Methods 53
1.6.3. Enzymatic Methods 61
1.7. Summary and Conclusions 54
1.8. References 66
3d
xit Contents
Chapter 2
Synthesis and Analysis of Stable Isotope and Radioisotope Labeled
Fatty Acids
Edward A. Emken
2.1. Introduction 77
2.2. Synthesis of Stable Isotope Labeled Fatty Acids 7®
2.2.1. Experimental Techniques ........ 7^
2.2.2. Saturated Fatty Acids 79
2.2.3. Monounsaturated Fatty Acids 82
2.2.4. Polyunsaturated Fatty Acids 84
2.2.5. Perdeutero Fatty Acids ........ 85
2.2.6. C Labeled Fatty Acids 88
2.3. Synthesis of Radioisotope Labeled Fatty Acids 91
2.3.1. 14C Labeled Fatty Acids 92
2.3.2. 3H Labeled Fatty Acids 94
2.3.3. Biosynthesis of 14C and H Labeled Lipids .... 99
2.4. Analysis of Radioisotope Labeled Fats ....... 102
2.4.1. Liquid Scintillation Counting 102
2.4.2. Radio Gas Chromatography 103
2.4.3. Thin Layer Chromatography ....... 105
2.4.4. Determination of Radiochemical Purity ..... 105
2.4.5. Chemical Degradation Methods 106
2.4.6. Storage of Radioisotope Labeled Fatty Acids .... 107
2.5. Analysis of Stable Isotope Labeled Fatty Acids 107
2.5.1. Mass Spectrometry 107
2.5.2. Infrared Spectrometry Ill
2.5.3. Nuclear Magnetic Resonance 112
2.6. Summary 115
2.7. References 115
Chapter 3
Separation and Determination of the Structure of Acylglycerols and Their
Ether Analogues
John J. Myher
3.1. Introduction 123
3.2. Nomenclature 123
3.3. Selected Methods for Modifying or Degrading Glycerolipids . . .124
3.3.1. Methanolysis 124
3.3.2. Saponification 124
3.3.3. Phospholipase C Hydrolysis 124
3.3.4. Acetolysis 125
3.3.5. Thermal Cleavage 125
3.3.6. Reductive Hydrogenolysis 125
Contents xiii
3.3.7. Grignard Hydrolysis 126
3.3.8. Oxidative Cleavage of Double Bonds 126
3.3.9. Hydrogenation 127
3.4. Derivatization Procedures 127
3.4.1. Acetates 127
3.4.2. Isopropylidenes 127
3.4.3. Trimethylsilyl Ethers 128
3.4.4. Tertiarybutyldimethylsilyl Ethers 128
3.4.5. Other Derivatives 129
3.5. Determination of the Structural Components of Glycerolipids . .129
3.5.1. Glycerol 129
3.5.2. Fatty Alcohols 131
3.5.3. Monoalkyl and Monoalk 1 enylglycerols 131
3.6. Extraction and Purification of Lipids 131
3.7. Thin Layer Chromatography 132
3.7.1. Plate Preparation 132
3.7.2. Detection of Neutral Lipids 133
3.7.3. Recovery of Lipids from Silica Gel 133
3.7.4. Separations on Silica Gel 133
3.7.5. Separations on Silica Gel Impregnated with Borate or Arsenite . 135
3.7.6. Separations on Silica Gel Impregnated with Silver Nitrate . .136
3.7.7. Reversed Phase TLC 138
3.7.8. Quantitation 139
3.8. Liquid Chromatography 139
3.9. Gas Chromatography 142
3.9.1. Column Packings 142
3.9.2. General Separation Characteristics 143
3.9.3. Equivalent Chain Length 144
3.9.4. Separation of Neutral Lipids 144
3.9.5. Quantitative Gas Chromatography 156
3.10. Mass Spectrometry 158
3.10.1. Monoacylglycerols 159
3.10.2. Monoalkylglycerols 163
3.10.3. Monoalk 1 enylglycerols 169
3.10.4. Diacylglycerols 171
3.10.5. Alkylacylglycerols 176
3.10.6. Triacylglycerols 176
3.10.7. Other Modes of Ionization 179
3.11. Other Techniques 180
3.11.1. Infrared Spectroscopy 180
3.11.2. Nuclear Magnetic Resonance Spectroscopy . . . .181
3.11.3. Optical Rotation and Stereospecific Analysis . . . .182
3.11.4. Calculation Methods 183
3.12. Combined Techniques 183
3.13. Conclusions 188
3.14. References 188
xiv Contents
Chapter 4
Stereospecific Analysis of Triacylglycerols
W. Carl Breckenridge
4.1. Introduction 197
4.2. Physical and Chemical Methods for the Determination of
Stereochemical Distribution of Fatty Acids in Triacylglycerols . .198
4.3. Enzymatic Methods for Determination of Stereochemical Distribution of
Fatty Acids in Triacylglycerols 200
4.3.1. Generation of Diacylglycerols 200
4.3.2. Stereospecific Selection of Diacylglycerols or Their Derivatives . 203
4.3.3. Calculations and Checks on Accuracy 205
4.3.4. Studies with Radioactive Acylglycerols 206
4.4. Positional Distribution of Fatty Acids in Natural Triacylglycerols . . 207
4.4.1. Animal Fats 208
4.4.2. Human Tissues ......... 220
4.4.3. Interorgan and Interspecies Comparisons ..... 223
4.4.4. Plant Oils 224
4.4.5. Yeast and Microorganisms 228
4.5. Concluding Remarks .......... 228
4.6. References 230
Chapter 5
Stereospec(fic Synthesis of Enantiomeric Acylglycerols
Dmytro Buchnea
5.1. Introduction 233
5.2. General Procedures for Specification of Absolute Configuration of
Enantiomeric s« Glycerol Derivatives ....... 234
5.3. Sources and Practical Methods for Preparation of Enantiomeric
sn Glycerol Derivatives 235
5.3.1. D Mannitol and L Mannitol ....... 235
5.3.2. Preparation of 1,2:5,6 Diisopropylidene D and L mannitols . 237
5.3.3. Preparation of 1,2 and 2,3 Isopropylidene s« glycerols . . 238
5.3.4. Preparation of 1 and 3 Benzyl s« glycerols .... 239
5.3.5. Preparation of Enantiomeric Alkyl and Alkenyl sn glycerols . 240
5.4. Methods of Configurational Conversion and Inversion of s« Glycerol
Derivatives . . . . . . . . . . . .241
5.4.1. Conversion of 1,2 Isopropylidene stt glycerol into 2,3
Isopropylidene src glycerol 241
5.4.2. Inversion of 3 Benzyl srt glycerol into 1 Benzyl srt glycerol . 243
5.4.3. Preparation of 1 Benzyl sw glycerol from D Mannitol via
l,3:2,5:4,6 O Trimethylene D mannitol . . . . .243
5.5. Selection of Protective Groups for Stereospecific Synthesis of Acyl ,
Alkyl , and Alkylacyl s« glycerols. ....... 244
5.5.1. Isopropylidene Group ........ 245
Contents xv
5.5.2. Benzylidene Group 246
5.5.3. Triphenylmethyl (Trityl) Group 246
5.5.4. Benzyl Group 247
5.5.5. 2,2,2 Trichloroethoxycarbonyl Group 247
5.5.6. Other Protective Groups 248
5.6. Stereospecific Acylation of Enantiomeric s« Glycerol Derivatives . . 248
5.6.1. Selection of Acylating Reagents 248
5.6.2. Synthesis of Enantiomeric 1 and 3 Monoacyl srt glycerols . 249
5.6.3. Synthesis of 2 Monoacyl s« glycerols 256
5.6.4. Synthesis of Enantiomeric 1,2 and 2,3 Diacyl sn glycerols . 256
5.6.5. Synthesis of Enantiomeric 1,3 Diacyl sn glycerols . . . 261
5.6.6. Synthesis of Enantiomeric Mixed Acid Triacyl SM glycerols . 263
5.7. Synthesis of Enantiomeric Isotope Labeled Acyl and
Alkylacyl sw glycerols 265
5.7.1. Synthesis of Enantiomeric Isotope Labeled Acyl sn glycerols . 265
5.7.2. Synthesis of Enantiomeric Isotope Labeled
Alkylacyl stt glycerols 266
5.8. Methods of Isolation and Purification of Synthetic Acyl s/j glycerols . 267
5.8.1. Selection of Solvents 267
5.8.2. Distillation and Crystallization 268
5.8.3. Chromatography 268
5.9. Determination of Structure and Absolute Configuration of Synthetic and
Natural Acyl sn glycerols 269
5.9.1. Chemical and Enzymatic Methods 269
5.9.2. Physical Methods 271
5.10. Summary and Conclusions 280
5.11. References 281
Chapter 6
Metabolic Studies with Natural and Synthetic Fatty Acids and
Enantiomeric Acylglycerols
Patrick J. A. O Doherty
6.1. Introduction 289
6.2. Activation of Fatty Acids 289
6.3. Biosynthesis of Phosphatidic Acid 291
6.3.1. Acylation of sn Glycerol 3 phosphate 291
6.3.2. Acylation of Dihydroxyacetone Phosphate .... 295
6.3.3. Synthesis of Phosphatidic Acid from Monoacylglycerols and
Diacylglycerols 296
6.3.4. Relative Contributions of the Pathways of Phosphatidic Acid
Synthesis 297
6.4. Biosynthesis of Diacylglycerols 299
6.4.1. Synthesis of Diacylglycerols from Monoacylglycerols . . 299
6.4.2. Synthesis of Diacylglycerols from Phosphatidic Acid . . 304
6.4.3. Synthesis of Other Diacylglycerols 306
* • Contents
6.5. Biosynthesis of Triacylglycerols . . . . . . . 310
6.5.1. Synthesis of Triacylglycerols from Diacylglycerols . . . 310
6.5.2. Triacylglycerol Synthetase . . . . . . 312
6.5.3. Relative Contributions of the Major Pathways of
Triacylglycerol Synthesis 312
6.6. Factors Influencing the Biosynthesis of Acylglycerols . . . .315
6.6.1. Nutritional Factors ......... 316
6.6.2. Hormonal Factors . . . . . . . . 317
6.6.3. Pharmacological Factors 317
6.7. Methods Employed in Studying the Biosynthesis of Acylglycerols . . 320
6.8. Kinetic Problems Encountered in Enzyme Assays Involving Lipid
Substrates 322
6.9. Enzymatic Lipolysis of Acylglycerols 324
6.9.1. Pharyngeal Lipases ......... 324
6.9.2. Pancreatic Lipase 324
6.9.3. Lipoprotein Lipase 325
6.9.4. Hormone Sensitive Lipase ....... 327
6.9.5. Monoacylglycerol Lipase ........ 328
6.10. Summary and Conclusions 328
6.11. References 329
Chapter 7
Composition of Selected Dietary Fats, Oils, Margarines, and Butter
Alan J. Sheppard, John L. Iverson, and John L. Weihrauch
7.1. Introduction 341
7.2. Methodology 344
7.2.1. Extraction Techniques 344
7.2.2. Esterification Techniques for Fatty Acids 346
7.2.3. Gas Chromatographic Analysis of Fatty Acid Methyl Esters . 347
7.2.4. Sterol Derivatization 348
7.2.5. Gas Chromatographic Analysis of Sterols 349
7.2.6. Lipoxidase:cw,c/s Polyunsaturated Fatty Acid Analysis . . 350
7.3. Basic Processing 352
7.3.1. General Discussion 352
7.3.2. Additives 354
7.3.3. Mayonnaise and Salad Dressing 355
7.4. Source Oils 356
7.4.1. Soybean 356
7.4.2. Cottonseed 357
7.4.3. Peanut 357
7.4.4. Corn 357
7.4.5. Safflower 360
7.4.6. Sunflower 360
7.4.7. Rapeseed 360
7.4.8. Other Cruciferae 361
Contents XVI (
7.4.9. Olive 361
7.4.10. Sesame 361
7.4.11. Cocoa 361
7.4.12. Palm and Palm Kernel 362
7.4.13. Coconut 362
7.5. Confectionery Products 362
7.6. Nuts 365
7.7. Cooking Oils 366
7.8. Shortenings 366
7.9. Margarines 36g
7.10. Dairy Products and Creamers 371
7.11. Animal Fats 372
7.12. Marine Products 372
7.13. Summary and Trends 374
7.14. References 375
Chapter 8
Fatty Acid Composition of Glycerolipids of Animal Tissues
Amis Kuksis
8.1. Introduction 381
8.2. Methods of Analysis 382
8.2.1. Isolation and Preparation of Fatty Acids 382
8.2.2. Quantitative Determination of Fatty Acids .... 383
8.2.3. Quality Control 384
8.3. Fatty Acids of Different Animal Species and Man 385
8.3.1. Differences among Homologous Tissues 385
8.3.2. Differences among Homologous Cell Types .... 394
8.3.3. Differences among Homologous Subcellular Fractions . . 396
8.3.4. Differences among Homologous Lipoproteins .... 402
8.4. Fatty Acids of Individual Animal Species and Man .... 406
8.4.1. Tissue Differences 406
8.4.2. Differences among Cell Types 419
8.4.3. Variations among Subcellular Fractions 424
8.4.4. Discrepancies among Plasma Lipoprotein Classes . . . 427
8.4.5. Characteristics of Skin Surface and Fecal Lipids . . . 429
8.5. Summary and Conclusions 435
8.6. References 437
Index 443
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| id | DE-604.BV006099483 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T16:40:16Z |
| institution | BVB |
| isbn | 0306335816 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-003852444 |
| oclc_num | 489885223 |
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| owner | DE-703 |
| owner_facet | DE-703 |
| physical | XVII, 469 S. graph. Darst. |
| publishDate | 1979 |
| publishDateSearch | 1979 |
| publishDateSort | 1979 |
| publisher | Plenum Pr. |
| record_format | marc |
| series | Handbook of lipid research. |
| series2 | Handbook of lipid research. |
| spelling | Fatty acids and glycerides Hrsg. von Arnis Kuksis* 2. print. New York u. a. Plenum Pr. 1979 XVII, 469 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Handbook of lipid research. 1. Acides gras ram Glycérides ram Glyceride (DE-588)4157720-6 gnd rswk-swf Lipide (DE-588)4035873-2 gnd rswk-swf Fettsäuren (DE-588)4154233-2 gnd rswk-swf Fettlösliches Vitamin (DE-588)4154227-7 gnd rswk-swf Fettlösliches Vitamin (DE-588)4154227-7 s DE-604 Glyceride (DE-588)4157720-6 s Fettsäuren (DE-588)4154233-2 s Lipide (DE-588)4035873-2 s Kuksis, Arnis Sonstige oth Handbook of lipid research. 1. (DE-604)BV000141923 1 HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=003852444&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Fatty acids and glycerides Handbook of lipid research. Acides gras ram Glycérides ram Glyceride (DE-588)4157720-6 gnd Lipide (DE-588)4035873-2 gnd Fettsäuren (DE-588)4154233-2 gnd Fettlösliches Vitamin (DE-588)4154227-7 gnd |
| subject_GND | (DE-588)4157720-6 (DE-588)4035873-2 (DE-588)4154233-2 (DE-588)4154227-7 |
| title | Fatty acids and glycerides |
| title_auth | Fatty acids and glycerides |
| title_exact_search | Fatty acids and glycerides |
| title_full | Fatty acids and glycerides Hrsg. von Arnis Kuksis* |
| title_fullStr | Fatty acids and glycerides Hrsg. von Arnis Kuksis* |
| title_full_unstemmed | Fatty acids and glycerides Hrsg. von Arnis Kuksis* |
| title_short | Fatty acids and glycerides |
| title_sort | fatty acids and glycerides |
| topic | Acides gras ram Glycérides ram Glyceride (DE-588)4157720-6 gnd Lipide (DE-588)4035873-2 gnd Fettsäuren (DE-588)4154233-2 gnd Fettlösliches Vitamin (DE-588)4154227-7 gnd |
| topic_facet | Acides gras Glycérides Glyceride Lipide Fettsäuren Fettlösliches Vitamin |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=003852444&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| volume_link | (DE-604)BV000141923 |
| work_keys_str_mv | AT kuksisarnis fattyacidsandglycerides |