Frank D. Gunstone

The Lipid handbook

Fatty acid structure. Lipid structure. Occurrence and characteristics of oils and fats. Separation and isolation procedures. Processing of fats and oils. Analytical methods. Synthesis. Physical properties - structural and physical characteristics. Physical properties - optical and spectral characteristics. Chemical properties. Lipid metabolism. Medical and agricultural aspects of lipids. Dictionary section. Compound name index. Formula index.

Vegetable oils in food technology: composition, properties and uses.

Preface to the First Edition. Preface to the Second Edition. Contributors. List of Abbreviations. 1 Production and Trade of Vegetable Oils ( Frank D. Gunstone ). 1.1 Extraction, refining and processing. 1.2 Vegetable oils: Production, consumption and trade. 1.3 Some topical issues. 2 Palm Oil ( Siew Wai Lin ). 2.1 Introduction. 2.2 Composition and properties of palm oil and fractions. 2.3 Physical characteristics of palm oil products. 2.4 Minor components of palm oil products. 2.5 Food applications of palm oil products. 2.5.1 Cooking/frying oil. 2.6 Nutritional aspects of palm oil. 2.7 Sustainable palm oil. 2.8 Conclusions. 3 Soybean Oil ( Tong Wang ). 3.1 Introduction. 3.2 Composition of soybean and soybean oil. 3.3 Recovery and refining of soybean oil. 3.4 Oil composition modification by processing and biotechnology. 3.5 Physical properties of soybean oil. 3.6 Oxidation evaluation of soybean oil. 3.7 Nutritional properties of soybean oil. 3.8 Food uses of soybean oil. 4 Canola/Rapeseed Oil ( Roman Przybylski ). 4.1 Introduction. 4.2 Composition. 4.3 Physical and chemical properties. 4.4 Major food uses. 4.5 Conclusion and outlook. 5 Sunflower Oil ( Maria A. Grompone ). 5.1 Introduction. 5.2 Sunflower oil from different types of seed. 5.3 Physical and chemical properties. 5.4 Melting properties and thermal behaviour. 5.5 Extraction and processing of sunflower oil. 5.6 Modified properties of sunflower oil. 5.7 Oxidative stability of commercial sunflower oils. 5.8 Food uses of different sunflower oil types. 5.9 Frying use of commercial sunflower oil types. 6 The Lauric (Coconut and Palm Kernel) Oils ( Ibrahim Nuzul Amri ). 6.1 Introduction. 6.2 Coconut oil. 6.3 Palm kernel oil. 6.4 Processing. 6.5 Food uses. 6.6 Health aspects. 7 Cottonseed Oil ( Michael K. Dowd ). 7.1 Introduction. 7.2 History. 7.3 Seed composition. 7.4 Oil composition. 7.5 Chemical and physical properties of cottonseed oil. 7.6 Processing. 7.7 Cottonseed oil uses. 7.8 Co-product uses. 8 Groundnut (Peanut) Oil ( Lisa L. Dean, Jack P. Davis, and Timothy H. Sanders ). 8.1 Peanut production, history, and oil extraction. 8.2 Oil uses. 8.3 Composition of groundnut oil. 8.4 Chemical and physical characteristics of groundnut oil. 8.5 Health issues. 9 Olive Oil ( Dimitrios Boskou ). 9.1 Introduction. 9.2 Extraction of olive oil from olives. 9.3 Olive oil composition. 9.4 Effect of processing olives on the composition of virgin olive oils. 9.5 Refining and modification. 9.6 Hardening and interesterification. 9.7 Quality, genuineness and regulations. 9.8 Consumption and culinary applications. 10 Corn Oil ( Robert A. Moreau ). 10.1 Composition of corn oil. 10.2 Properties of corn oil. 10.3 Major food uses of corn oil. 10.4 Conclusions. 11 Minor and Speciality Oils ( S. Prakash Kochhar ). 11.1 Introduction. 11.2 Sesame seed oil. 11.3 Rice bran oil. 11.4 Flaxseed (linseed and linola) oil. 11.5 Safflower oil. 11.6 Argan kernel oil. 11.7 Avocado oil. 11.8 Camelina seed oil. 11.9 Grape seed oil. 11.10 Pumpkin seed oil. 11.11 Sea buckthorn oil. 11.12 Cocoa butter and CBE. 11.13 Oils containing a-linolenic acid (GLA) and stearidonic acid (SDA). 11.14 Tree nut oils. Useful Websites. Index.

Fatty acids. Part 50. 13C nuclear magnetic resonance studies of olefinic fatty acids and esters.

Abstract The 13 C-NMR spectra of 48 cis alkenoic acids and esters (C 8 –C 20 ), 18 trans alkenoic acids and esters (C 9 –C 18 ), and 26 polyenoic acids and esters (C 18 –C 22 ) are reported and interpreted. The characteristic features of such spectra which permit structural assignments to be made are discussed.

Lipid technologies and applications

Introduction: fatty acids and lipid structure major sources of lipids phospholipids lipids and nutrition. Processing: extraction of lipids from natural sources refining oil storage, transport, and handling fractionation interesterification of oils and fats hydrogenation of edible oils - technology and applications. Food emulsions: butter, margarine, spread, and baking fats ice cream cream alternatives. Nonaqueous foods: ghee, vanaspati, and special applications of fats in India chocolate and confectionery fats frying oils and salad oils. Special food applications: edible coating and film barriers spray processing of fat-containing foodstuffs - spray drying and cooling low calorie fats food emulsifiers lipid emulsions for intravenous nutrition and drug delivery the role of lipids in animal feeds. Nonfood uses: anionic detergents cationic surfactants nonionic surfactants lipids - their use in personal care products the use of oils and fatty acids in paints and surface coatings lubricants epoxidized oils bio-fuels products from castor oil.

Enzymes as biocatalysts in the modification of natural lipids

Though designed by nature to effect hydrolysis of lipids, lipases can, under appropriate reaction conditions, promote ester formation through reaction of acids and alcohols (esterification) or of esters with acids (acidolysis), alcohols (alcoholysis), or other esters (interesterification). Compared with chemical processes already carried out on an industrial scale enzymic reactions occur under milder (and ‘greener’) conditions though they may take longer. Of greater significance is the specificity shown by the enzymes which permits the formation of lipid derivatives not easily prepared by conventional laboratory procedures. This review describes the lipases and their various specificities and reports on their use in hydrolysis and in the production of phospholipids, fatty acids, alkyl esters, mono- and di-acylglycerols, triacylglycerols, other esters, and amides. Some of these have already led to marketable products but for the most part the full potential of these reactions has yet to be realised. The reactions of other enzymes promoting interesting reactions at unsaturated centres are also described. © 1999 Society of Chemical Industry

Desaturation of positional and geometric isomers of monoenoic fatty acids by microsomal preparations from rat liver

A range ofcis- andtrans-monoenoic fatty acids was tested as substrates for desaturation in microsomal preparations from rat liver.Trans-monoenoic acids were generally desaturated in the Δ9 position to the same extent as stearic acid. Acids with Δ7-trans- and Δ11-trans-olefinic unsaturation produced Δ7-trans,9-cis- and Δ9-cis,11-trans-conjugated dienoic acids, respectively, but the Δ8-trans- and Δ10-trans-monoenoic acids did not give Δ8,9- or Δ9,10-allenes. Of thecis-monoenoic acids examined, only those with double bonds at or beyond the Δ14 position gave any measurable Δ9 desaturation. When Δ9 desaturation of long chain saturated acids was inhibited by adding sterculic acid, these saturated acids were desaturated at the Δ5 and Δ6 positions. Many of the monoenoic acids tested were also desaturated at the Δ5 and/or Δ6 positions, although the percentage conversions were always low. Δ9-cis,11-trans-, Δ9-cis,12-trans- and Δ9-cis,13-trans-dienoic acids, produced in situ by Δ9 desaturation of the corresponding monoenoic acids, were extensively desaturated in the Δ6 position. These results are discussed in terms of: (a) the various models proposed to explain the substrate specificities of the desaturases, and (b) the metabolism of unnatural fatty acids ingested from dietary sources.

Fatty acids, part 16. Thin layer and gas—liquid chromatographic properties of the cis and trans methyl octadecenoates and of some acetylenic esters☆

Abstract The chromatographic properties of the cis and trans methyl octadecenoates and of some C12 and C18 acetylenic esters on thin layers of silica impregnated with silver nitrate and on some GLC systems are reported. The possibility of identification and separation of these isomers is discussed.

Isomers in commercial samples of conjugated linoleic acid

In connection with our analytical activities (MRS Lipid Analysis Unit), we have analyzed several commercial samples of conjugated linoleic acid (CLA). Most of these have been prepared by alkali-isomerization of linoleic acid or of oils, such as sunflower or safflower, rich in this acid. (i) We have examined the methyl esters, which must be prepared from the acids avoiding the use of acidic catalysts, by gas chromatography (GC). With a 25-m carbowax capillary column, most of the samples show two major peaks which are well-resolved from each other, along with minor peaks running later which are first the all-cis and then the all-trans dienes. The two major peaks are usually considered to be only the 9c,11t and 10t,12c isomers. This interpretation is not consistent with the GC/mass spectrometry (MS) data reported below. When examined on a highly polar 100-m capillary column (CP Sil 88), the GC trace is more complex. Several samples show a new peak for 11,13 diene, and some indicate the presence of several other isomers. We also have evidence that the 9,11 peak contains the 8,10 isomer though we have been unable to resolve these. (ii) GC–MS of the diene adducts formed through reaction with 4-methyl2,3,4-triazoline-3,5-dione (MTAD derivatives), with selected ion monitoring, shows the presence of 8,10; 9,11; 10,12; and 11,13 dienes (1). For example, Figure 1 illustrates the selected ion chromatogram for one of the diagnostic ions from each isomer in a commercial CLA preparation. It is clear that four unresolved isomers are present. The proportions of these vary widely (presumably depending on the conditions of alkali-isomerization) and even more isomers are sometimes present. GC–MS of the dimethyloxazoline derivatives confirmed the identity of the major products. (iii) High-resolution 13C nuclear magnetic resonance spectroscopy confirmed the presence of at least four cis,trans conjugated dienes and gave quantitative results in line with those obtained by GC–MS analysis. We conclude that most samples of CLA, though rich in the 9,11 (probably mainly if not entirely the 9c,11t isomer) and 10,12 dienes (probably mainly if not entirely the 10t,12c isomer) also contain at least the 8,10 and 11,13 cis,trans dienes, sometimes at quite high levels. These are accompanied by allcis and all-trans dienes. In one commercial sample of CLA, we found the following dienes: 8,10 (14%), 9,11 (30%), 10,12 (31%), and 11,13 (24%). It is important that those who produce these materials and use them for research purposes appreciate the complex nature of their products. To our knowledge, the identity of the biologically active CLA is not known although it is generally assumed to be 9c,11t-18:2. Nor is it known how the activity of this isomer may be influenced by the presence of other isomeric CLA.

Fatty acids, Part 35 the preparation and properties of the complete series of methyl epoxyoctadecanoates☆

Abstract The complete series of methyl epoxyoctadecanoates (31 isomers) has been made by epoxidation of the octadecenoates. The melting points of the acids are reported along with the chromatographic (TLC and GLC) and spectroscopic (NMR and MS) behaviour of the methyl esters.

Fatty acids. Part 13. The synthesis of all the cis n-octadecenoic acids

Abstract All the cis n-octadecenoic acids (Δ2–Δ17) have been synthesised along with several dodecenoic (Δ7–Δ11), dodecynoic (Δ7–Δ11), and octadecynoic (Δ2, Δ4–Δ12) acids required as intermediat es.