THE OILY PRESS

Written by Kare Larsson, Peter Quinn, Kiyotaka Sato and Fredrik Tiberg. Published 2006, ISBN-13: 978-0-9531949-9-5 (ISBN-10: 0-9531949-9-X)

On this page you can read a Forward by the Publisher, the Author's Preface, and reviews of this book written in the scientific literature. For more details of the chapters and to buy the book, please see the main Lipids: Structure, Physical Properties and Functionality web page.

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Foreword | Preface | Reviews

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Over ten years have passed since the publication of Kåre Larsson’s Lipids – Molecular Organization, Physical Functions and Technical Applications (LMO) by The Oily Press, then based in Dundee, Scotland, and run by Dr William W. Christie. The book was soon recognized as a major contribution to the literature (“This is a book without comparison in the lipid literature...”, Stig E. Friberg in the Journal of Dispersion Science and Technology, 1995, Vol. 16, p. 295 and “... the content is excellent”, Philip W. Wertz in Chemistry and Physics of Lipids, 1994, Vol. 74, p. 99). Dr Christie’s excellent choice of Kåre Larsson as the author was also confirmed (“His expertise in describing the various states of lipids is second to none”, Edward G. Perkins in INFORM, 1994, Vol. 5, p. 1394 and “... written by an acknowledged world expert in his field”, Fred B. Padley, Lipid Technology, 1994, Vol. 6, p. 102). Until the publication of LMO there had been no single, concentrated source of so much information on the subject: “The strength of this book – and it is enormous – is the fact that the author has been able to compile in one volume information otherwise found only in the most widely different kinds of scientific journals” (Friberg).

When LMO was published, Kåre Larsson was a Professor of Food Technology in the Chemical Centre at Lund University, Sweden. He is now cofounder of Camurus AB and Probi AB, and earlier of Biogram AB (which later became Bioglan AB), and serves as Chairman of the Board of the Camurus Lipid Research Foundation in Lund. Camurus is a provider of drug delivery systems and works closely with pharmaceutical manufacturers. Kåre Larsson is a Fellow of the Royal Swedish Academy of Science and the Academy of Engineering Science and has authored more than 200 original papers and five books covering areas of lipid biophysical chemistry, food science and nutrition, and biomedicine. He is also the named inventor on several patents, of which four have led to industrial products. In 2001 he won the Rhodia prize of the European Colloid and Interface Society for his discovery of cubosomes and hexosomes and explorative work on their applications.

When I asked Kåre Larsson to write a second edition, the comprehensive coverage of LMO became an obstacle – the subject area had expanded to such an extent that one author could not cover it alone. But we did not want to resort to the usual edited book with each chapter written by a different author. The solution was to invite three other well-known scientists in this field to act as coauthors – and it is a tribute to Kåre’s reputation that all three agreed.

Peter Quinn, Professor of Biochemistry in the Department of Life Sciences at King’s College London, UK, is renowned for his work on biological membranes and their constituents, as evidenced by the publication of ten books, more than 400 research papers, and several patents.

Kiyotaka Sato, Professor in the Graduate School of Biosphere Sciences, Hiroshima University, Japan, is widely recognized as a leading expert in the physical chemistry and biophysics of fats and lipids and in the crystallization of biological soft materials. Among other awards, he was presented with the 2005 AOCS Stephen S. Chang Award for distinguished accomplishments in basic research that have been used by industry for the improvement or development of products related to lipids in the area of lipid crystallization and crystallography.

Fredrik Tiberg is President, Chief Executive Officer and Head of Research & Development at Camurus AB, and also Adjunct Professor of Surface and Colloid Chemistry at Lund University. He has published more than 80 original scientific papers, coauthored several books, and been named as inventor on a number of patents.

With some major changes in the areas covered, and with four authors instead of one, we were obliged to define the resulting publication as a new book with a new ISBN number, rather than as a second edition retaining the old number. Therefore we took the opportunity of also giving it a new and more appropriate title: Lipids: Structure, Physical Properties and Functionality. With the knowledge and experience of the above-named four authors behind it, I am confident that this new book will build on the reputation of LMO and be a valued source of information for many years to come.

The ambition behind the new edition of this book is to provide an up-to-date description of the diversity of lipid molecular arrangements in different physical states, as a basis for the understanding of lipid functionality in biological and technical systems. The first edition was published in 1994 with Kåre Larsson as author, and when he was asked by the publisher to revisit the text he realized that he could not cover this broad field alone. Three colleagues joined forces with him, and the present edition has therefore in many aspects been extended. In some cases the description is deeper with a more narrow focus. For example, the chapter on the solid state in the earlier edition covered all lipids, whereas in this new edition there is a very complete demonstration of the crystal structures and crystallization properties of fatty acids and fats. These general principles, however, can be applied to all lipids.

In biology, as well as in technical applications such as foods, we are dealing with soft matter. Lipids form aqueous phases alone or in conjunction with proteins and polysaccharides. The combination of short-range disorder and long-range order into liquid-crystalline structures plays a crucial role. A driving force is the dualistic properties of the molecules in relation to water. Molecular regions avoiding water contact, in combination with regions striving towards such contact and interaction, lead to self-assembly, and even in the liquid state to the formation of organized structures on the colloidal level. This new edition presents many new results, particularly on the structure and functions of dispersions of liquid-crystalline phases forming nanostructures and mesoporous systems.

With regard to the role of lipids in cellular and molecular biology, this book focuses on biophysical aspects, and discussion of lipid biochemistry is limited to a chapter on cell membranes.

Kare Larsson, Peter Quinn, Kiyotaka Sato and Fredrik Tiberg

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Dr J. Peter Slotte, Abo Akademi University, Turku, Finland, writing in European Journal of Lipid Science and Technology, 2008, Vol.110, p.593.

This book is the ninteenth contributon to the Oily Press series of book on lipids and lipid technology. Although branded as a new book, it is in fact a revised edition of a previous book (Lipids - MoIecular Organization, Physical Functions and Technical Applicatons by Kare Larsson, 1994, The Oily Press).

The physical properties of lipids and lipid aggregates in the dry and hydrated state are covered in depth, and the industrial and technical/application point of view is never far away. The treatment of some topics in the book is very comprehensive and state of the art, whereas other chapters are more brief and only "scratch the surface". The focus in the book is more on the propertes of the aggregate state than on properties of individual lipid species (the two are of course inter-related and inter-dependent to a significant extent). The molecules discussed belong dominantly to simple (fatty acids) and nonpoIar 1ipid classes (diacyl- and triacylglycero1s). Only occasionally are more complex membrane lipids (phospholipids, sphingolipids) dealt with in more detai1 (chapters 9 and 10).

The chapter on solid state behaviour of lipids and fatty acids (chapter 2) is extensive and the treatment of the subject is clear and complemented with many supporting figures and schemes. This chapter, together with chapters on liquid crystalline lipid-water phases (chapter 3), the liquid state (chapter 4), lipid behaviour at interfaces (chapter 5; surface films, bubb1es and foams), and lipid dispersions in water (chapter 6)comprise about half of the book. The topics are covered from technical, physical and biological points of view and are informative with up to date referencing.

The remaining half of the book deals with interactions of lipids with proteins (chapter 7), emulsions (chapter 8; o/w and w/o), lipids in biological membranes (chapter 9), lipids in barrier function (chapter 10) and drug delivery (chapter l l), and finally lipids in foods (chapter 12). Of these topics, the chapter on lipids in biological membranes is the one which has undergone the heaviest revision compared to the previous version of the book. The membrane lipid composition is discussed in relation to recent advances in mass spectrometry,and membrane structure is discussed based on new knowledge of domains and the lateral structure of membranes. The second half of the chapter on lipids in biological membranes is devoted to function, lipid diversity and adaptation. It contains a good discussion on 1ipid remodeling and includes a thorough section dealing with the central lipases that are involved in that process and in the maintenance of lipid homeostasis in general.

The layout of the book is classical Oily Press format, with many hand-drawn figures and schemes in black-and-white (the book includes about 120 figures and micrographs altogether). The number of listed references reaches about 600, but there is some redundancy among references in different chapters. The book is well written and easy to read, and its chapter structure and content is logically laid out. The book is a valuable addition to lipidologists and certainly useful for scientists working in fields where lipids are not the core interest but still have importance for solving scientific and/or technica1 issues.

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Ian C. Baianu, University of Illinois at Urbana-Champaign, Illinois, USA, writing in Inform (magazine of the American oil Chemists Society), June 2008, Vol.19, No.6, p.404.

This is a well-organized book covering extensively the fundamental aspects of fats and fatty acid structures, including a concise review in the first three chapters of liquid-crystalline structures and lipid-water phases. This topic is elegantly presented and precisely illustrated with numerous figures. Lipid dispersions in water as well as lipid monolayers and multilayers are discussed in Chapters 5 and 6, with a brief section covering structure-functionality relationships.

The interactions of lipids with proteins and polypeptides are summarily addressed in Chapter 7, mostly in a biochemical vein, thus missing much of both classical and recent findings from either magnetic resonance or laser/fluorescence spectroscopy. A very brief outline of emulsions is provided in Chapter 8, but the discussion lacks a clear explanation of how emulsions are either formed or stabilized.

Membrane lipid composition is succinctly presented in Chapter 9, and high quality illustrations of membrane cross-sections/internal structures are provided as freeze-fracture electron micrographs of chloroplasts and thylakoid membranes. Biochemical, metabolic, and genetic aspects of lipid homeostasis are also concisely presented in Chapter 9, with special emphasis on phospholipases A2, C , D, and the acyltransferases from several bacteria (e.g., E. coli, B. cereus, and Pseudomonas faciens). The lipid bilayer asymmetry found in biomembranes is emphasized and the transbilayer asymmetry generated by ATP-dependent aminophospholipid translocases is also discussed, however, without entering into either detailed physicochemical mechanisms or their deeper physiological implications for membrane bioenergetics.

The last two chapters summarize very important applications of liposomes to drug delivery and lipid interactions in foods. The latter topic is, unfortunately, only very generally sketched in the last chapter (12), below the level of undergraduate courses in food chemistry. Overall, the book contains eleven worthwhile chapters that cover a surprisingly wide range of fat and specific, lipid related topics that are of marked quality in contrast to the final chapter on food applications. The interesting lipid-related topics covered in the book could be readily expanded to a standard textbook twice the size of this compact book.

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Dr Stig E. Friberg, University of Virginia, Charlottesville, Virginia, USA, writing in Journal of Dispersion Science and Technology, 2007, Vol.28, p.653.

"This is a tremendous combination of talent and the book bears witness to the same. In spite of the large number of authors the book is an organic unity describing the different aspects of lipid science and technology in a condensed and readable form.....The book is written in an outstanding manner and there is no need for detailed information about the different chapters....The book is truly and strongly recommended to anyone not only in the field of lipids but also to colloid chemists in general."

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Dr Sven Engström, Chemical and Biological Engineering, Chalmers University of Technology, Gothenburg, Sweden, writing in Lipid Technology, July 2006, Vol.18, No.7, pp.165-166.

"If you want to understand function, study structure" is a phrase used by Francis Crick and is also an underlying theme of this book written by Larsson, Quinn, Sato and Tiberg. The book can be regarded as (but is not) a second edition of Kåre Larsson's Lipids — Molecular Organization, Physical Functions and Technical Applications, published in 1994. The impact from the new authors is clearly distinguishable in the chapters dealing with solid-state behaviour (Sato), lipid dispersions (Tiberg) and lipids in biological membranes (Quinn).

The book is divided into 12 chapters, and every chapter ends with an up-to-date reference list. There are numerous figures and diagrams supporting the text in each chapter. Here and there one recognizes Larsson's ‘hand-drawn-with-a-marker-pen-figures’, a refreshing reminder of the past when less time was spent on finding fancy colour schemes and other visual effects compared with today's computer graphics. Chapters 1–5 (about 130 pages) deal with definitions, solid-state, liquid-crystalline state, liquid state and interfacial behaviour of lipids. The most extensive chapter, more than 20% of the entire book, deals with the solid-state behaviour of fats and fatty acids. This chapter ends with a reference list with more than 140 titles, 80 of them published 1994 or later. For scientists working with lipids in the solid-state, this chapter should be a gold-mine.

In chapter 6 — ‘Dispersions of lipid-water phases’ — the authors present the fascinating non-lamellar ‘Cubosomes’, ‘Hexosomes’ and ‘Flexosomes’ in some detail with beautiful electron micrographs, and relate these ‘-somes’ to the classical liposomes as well as non-lamellar structures in biological systems.

In the rest of the book, the interaction, functionality and application of lipids in various situations are presented. Chapter 7 deals with lipid-protein/polypeptide interactions and chapter 8 with emulsions and emulsion stability. In chapter 9 — ‘Lipids of biological membranes’ — the reader is given a state-of-the-art presentation of membrane lipid chemical analysis, lipid composition and domain formation in biological membranes, membrane function and the biochemistry of lipid homeostasis. As in the solid-state chapter, chapter 9 includes more than 140 references, of which 56 are published in 2000 or later.

The last three chapters deals with lipids as barriers towards the outer environment in skin, gastrointestinal tract and the lung (Ch.10), drug delivery (Ch.11) and foods (Ch.12). Compared to the 1994 book, the food chapter is less than half its size in the new book. This may be seen as a reflection of lipid science entering into new areas, not least as a consequence of the efforts made by the former professor of food technology Kåre Larsson himself.

Since no single chemistry discipline (organic chemistry, biochemistry) teaches the properties of lipids to any greater extent than the others, I strongly recommend this book to anyone working with lipids both in fundamental as well as in applied research. I have used the 1994 book to introduce lipids to graduate and even undergraduate students with great success, and I will not hesitate to use the new book in the same way.

We have provided below several reviews of the earlier version, Lipids - Molecular Organization, Physical Functions And Technical Applications, which was written by Kare Larsson. As explained in the Foreword and Preface shown above, the new book is based on this earlier version. However, it was extended and three co-authors joined Kare Larsson to write the new version under a new title and new ISBN number. The earlier reviews shown below give some idea of the content and quality of the book and how well it was received. However the breakdown into chapters and the chapter headings are not the same for the two books.

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Book reviews of Lipids - Molecular Organization, Physical Functions And Technical Applications, written by Kare Larsson, published by The Oily Press in 1994.

Dr Fred B. Padley (Unilever Research, Bedford, UK) writing in Lipid Technology, 1994, Vol.6, p.102.

It is one thing to have a knowledge of the chemical composition of multi-component products, but to combine this with a knowledge of the structure is to know the product. It has therefore been a long-standing goal of scientists working on complex systems to relate composition to structure and physical behaviour. This has been especially true in food research. An understanding of the inter-relationships between composition, product processing, with texture, mouthfeel and flavour release, can lead to significant advances in the generation of new and improved products and processes. This was, and still is, done by devising suitable hypotheses and testing these out using appropriate experiments to validate predictions, for example the use of pictorial representations and mathematic theory to predict the rheology of complex systems.

The advance of physical measurement techniques proceeds at what appears to be an ever accelerating rate. The combination of computerized data handling and improved electronics has led to a resurgence of spectroscopic techniques, This has given them a new lease of life, providing the scientist with new sensitive methods for characterizing molecular behaviour.

Great strides have also been made in the field of microscopy with the advent of the scanning tunnelling and atomic force microscopes. Publications in this area are still somewhat limited because commercial instruments have only been available relatively recently. The ability to view structures at an atomic level will greatly enhance our knowledge and our ability to predict the behaviour of complex systems.

One ultimate goal is the dynamic observation at a submicroscopic level of product behaviour during transformation. For example, the phase inversion of emulsified products such as creams from oil-in-water to water-in-oil structures. We can anticipate that, slowly but surely, we will gain a much deeper understanding of these complex products with the advent of these new methods of physica1 measurement. In the meantime however most scientists have to make the best use of more readily available techniques to further our understanding.

The recent publication of Lipids — Molecular Organisation, Physical Functions, and Technical Applications written by Kare Larsson is therefore a very welcome addition to the literature. This reviewer is not aware of any related work which discusses the structure of such a wide range of food and non-food products as is presented here in such a concise way. In his preface Professor Larsson outlines his objective: "To describe the remarkable diversity of lipid structures as a basis for the understanding of lipid functionality in biological and technical systems".

The general principles relating to solid-state, liquid crystalline, liquid and dispersed systems are described, together with chapters covering surface chemistry and lipid-protein interactions. The physical basis behind these various phenomena is described in a lucid and concise way. The great diversity of topics covered in the second half of the book will be of great interest and value to a wide audience working not only in research and development but also in the teaching profession. It is not the intention of this review to provide a complete catalogue of topics. Suffice to say that the numerous topics covered range from lipids in biomembranes including skin, to lipids in baking, and from food emulsions to drug delivery.

This is a concise book written by an acknowledged world expert in his feld. It is a book to be read by those interested in understanding the behaviour of lipids and gaining a new insight to their applications.

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Stig E. Friberg writing in the Journal of Dispersion Science and Technology 1995, Vol.16, p.295.

This is a book without comparison in the lipid literature; it treats the entire spectrum of lipid properties from a short introduction about the chemical structure of lipids, thin molecular organization in all states; solid, liquid crystalline and liquid as well as their behavior in monomolecular layers and interaction with proteins.

After these initial chapters, laying the groundwork, follows eight chapters of applications covering all essential aspects of lipid activity: vesicles, emulsions, lubrication, biomembranes, human skin (cosmetics and drug penetration) and gastrointestinal tract, drug delivery and foods. Finally a short chapter is found about future aspects of functional application of lipids.

The strength of this book - and it is enormous - is the fact that the author has been able to compile in one volume information elsewise found only in the most widely different kinds of scientific journals. The book will be extremely useful for all branches of food, cosmetics, pharmaceutics, and household products that formulate with lipids. It is strongly recommended as a textbook within the undergraduate junior and senior programs as well as the graduate level within these educational institutions.

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Edward G. Perkins (University of Illinois Urbana, Illinois, USA) writing in INFORM 1994, Vol.5, p.1394.

This latest offering from The Oily Press is written by Professor K.A. Larsson, who has had considerable experience in the study of lipid structures derived from crystallization, etc. His expertise in describing the various states of lipids is second to none.

This volume is divided into Part I: Fundamental Aspects, which covers the basic concepts of lipids, their structure, properties and methods of characterization. Solid-state behavior in which crystallization, packing features of lipids in crystals illustrating polymorphism, etc., is discussed. Polar and nonpolar lipids are treated in a similar fashion. Fat crystallization in glycerides, both simple and mixed, and phase diagrams are illustrated. The complexities of gel phases and of liquid crystalline lipid water phases, phase transitions, binary and ternary phase diagrams and the behavior of different lipids, including cholesterol ester liquid crystals, are next discussed.

The author goes on to discuss the liquid state, monolayers in surface films, bubbles and foams, lipid interaction with proteins and other polymers, and dispersion of lipid-water phases.

In Part 2, the author covers more practical considerations by discussing emulsion science and technology, lipids in biomembranes, lipids in lubrication, the role of lipids human skin, in drug delivery, the function of lipids in foods, and the future aspects of functional roles for lipids.

A comprehensive index, as well as a detailed reference list, is appended to the book. This book should have wide appeal to formulators, chemists, graduate students and anyone who needs detailed structural information of lipids and their polymorphs, etc.

Although a very difficult topic is undertaken, the book is written clearly with many illustrations to help the reader to gain an understanding. It should be used extensively by many varieties of lipid chemists.

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W. Wertz (University of Iowa Iowa City, Iowa, USA) writing in Chemistry and Physics of Lipids, 1994, Vol.74 pp.99-100.

This monograph is the latest in the very useful series from The Oily Press. The cover of this book is not of high quality, but the content is excellent. The text is divided into two parts: Part 1, Fundamental Aspects (seven chapters, 116 pages) and Part 2, Lipid Functionality (8 chapters, 96 pages).

Chapter 1 (Basic Concepts) introduces some basic terminology and discusses briefly the relationships among lipid chemical structure, physical properties and functional properties. X-ray diffraction, NMR and Raman spectroscopy are presented as methods for characterization of lipid structure.

Chapter 2 (Lipids in the Solid State) discusses crystallization of lipids, lipid crystal forms and hydrocarbon chain packing. Solid-state behavior of a series of specific polar and non-polar lipids is summarized, and significant attention is paid to fat crystallization and the formation of gel phases on interaction with water. Chapter 3 (Liquid-Crystalline Lipid-Water Phases) presents discussions of lamellar, hexagonal and cubic liquid-crystalline phases. Phase transitions and phase diagrams are addressed, and a number of specific examples are given.

Chapter 4 (The Liquid State) deals with the liquid state and includes discussion of oils, L2 and L3 phases and mieroemulsions. Freeze fracture electron micrographs are included to illustrate these different lipid states. Chapter 5 (Monolayers in Surface Films, Bubbles and Foams) discusses the formation, structure, stability and dynamics of lipid monolayers at interfaces.

Chapter 6 (Lipid Interaction with Proteins and Other Polymers) includes brief discussions of protein folding and unfolding as a result of interaction with sodium dodecyl sulfate. Subsections deal with binding of fatty acids to serum albumin and trans- port of circulating lipids by lipoproteins. The different types of interactions between proteins and liquid crystalline phases and monolayers are covered, and a final section discusses interactions of lipids with polymers other than proteins.

Chapter 7 (Dispersions of Lipid-Water Phases) introduces the reader to dispersions of La phase in water, or liposomal dispersions, which are discussed in greater detail in a later chapter. Aqueous dispersions of hexagonal phase, cubic phase, L2 and L3 phases and lipid crystals are also covered here. Chapter 8 (Emulsion Science and Technology) presents in detail the factors governing stability and breakdown of emulsions in general, with specific discussions of oil-in-water and water-in-oil emulsions. The role of emulsification in fat digestion is also addressed.

Chapter 9 (Lipids in Biomembranes; Drug Penetration through Membranes, Membrane Mimicking) covers the roles of lipids in biomembrane structure and relates lipid phase behavior to membrane functions. The roles of glycolipids in specific recognition phenomena are discussed. The penetration of pharmaceutical agents through cell membranes and the possible use of lipid coatings to improve biocompatability of medical implants or devices contacting blood are examined.

Chapter 10 (Lipids in Lubrication) contains sections dealing with lubrication in general and with the specific lubricating properties of liquid-crystalline phases, crystalline phases and grease and plastic fats. Chapter 11 (The Role of Lipids in Human Skin: Skin Care Formulations and Drug Penetration) discusses sebaceous lipids, which are secreted onto the skin surface, as well as epidermal lipids and their role in the permeability barrier of the skin. A section on skin care formulations considers both external and penetrating formulations, and a final section deals with the roles of lipids in transdermal drug delivery.

Chapter 12 (Polar Lipids in Gastrointestinal and Pulmonary Surface Layers and Administration of Exogenous Phospholipids) begins by introducing the reader to the mucous layer coating the gastrointestinal tract and to lung surfactant. This is followed by more extensive discussions of the roles of lipids in the gastrointestinal lining, the intestinal absorption of lipids and pulmonary surfactant. Chapter 13 (Drug Delivery) considers the potential uses of lipid emulsions, liposomal dispersions, cubic phases and lipid crystal dispersions for the delivery of drugs by parenteral, oral and transdermal routes.

Chapter 14 (Lipid Functionality in Foods) covers a wide range of topics, including sections addressing the modification of starch by lipids, milk-based lipid products, cocoa butter and chocolate, oils and oil-water emulsion products, lipids in baked products, lipid oxidation, nutrition, fat substitutes and encapsulation of lipids as a means of retarding oxidation. Chapter 15 (Future Aspects of Functional Applications of Lipids) speculates on the development of new oilseed crops and oil processing methods, enzyme technology, biosurfactants and technologies based on supercritical and high-pressure carbon dioxide.

This volume is authoritatively written and well illustrated (107 illustrations) and includes a subject index and a bibliography of 362 references. It would be a useful reference for investigators working in the areas of lipids, food science or pharmaceutical technology, and would be a suitable text for use in a graduate-level course on the physical chemistry of lipids.

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