Polar Lipids

Biology, Chemistry, and Technology

Moghis U. Ahmad, Xuebing Xu

• Publisher: Academic Press and AOCS Press
• Year: 2015
• ISBN:
  9781630670450
• Topic: Biological Sciences
• Subtopic: Biochemistry
• Index: Biological Sciences

Polar Lipids is a valuable reference resource providing thorough and comprehensive coverage of different types of polar lipids known to lipid science and industry today. This book covers important applications and utilization of polar lipids, either in the area of food and nutrition, or health and disease.

Each chapter covers chemistry and chemical synthesis, biosynthesis and biological effects, functional and nutritional properties, applications, processing technologies, and future trends of a variety of polar lipids—including glycolipids, ether lipids, phenol lipids, serine phospholipids, omega-3 phospholipids, rice lecithin, palm lecithin, sunflower lecithin, sugar- and protein-based lipids, lysophospholipids, and more.

• Presents new and relatively unexplored polar lipids for researchers to consider to use in food and health applications
• Includes details on the chemistry and chemical synthesis, biosynthesis and biological effects, functional and nutritional properties, applications, and future trends of a variety of polar lipids
• Presents the latest analytical techniques for use in polar lipids research, including NMR and Supercritical Fluid Chromatography/Mass Spectrometry

1

Soybean Lecithin: Food, Industrial Uses, and Other Applications

G.R. List, USDA, Retired

Introduction

Lecithin has long been an important component of a myriad of both food and nonfood products and is one of the most versatile and valuable byproducts of the oilseed industry. In foods, lecithin provides about a dozen functions, including as an emulsifier, as a wetting agent, for viscosity reduction, as release agents, and for crystallization control. Lecithin also provides functions in numerous industrial applications as well (Hilty, 1948; Sipos, 1989). Much of the lecithin technology was developed in Germany by Bollman and Rewald who held a number of patents describing the process of recovering phosphatides from oilseeds(Bollmann, 1923, 1928, 1929). Bollman also patented a process for improved salad oil manufacture (Bollman, 1926). By 1940, the U.S. lecithin industry was well established (Wendel, 2000). The emulsifying and other functional properties of lecithin were well-recognized and incorporated in numerous foods including margarine, shortenings, baked goods, chocolates, candy, macaroni and noodles, ice cream, instant cocoa beverages, powdered milk, and as crystal inhibitors and antioxidants in fats and oils (Eichberg, 1939; Wiesehahn, 1937). Moreover, a number of nonfood uses were described, including petroleum lubricants, textiles, leather, coatings, rubber, resins, and soaps. The benefits of lecithin were recognized by the cosmetic and pharmaceutical industries as well (Wittcoff, 1951). Phosphatides may undergo numerous chemical reactions including autoxidation, complexing with metal ions, and reactions within the fatty acids or the phosphatide groups (Ghyczy, 1989; Pryde, 1985). However, only a few have been exploited by the industry.

Much of the work on chemical modification of phosphatides, including sulfonation (Scharf, 1953), halogenation (Denham, 1939), hydroxylation (Wittcoff, 1948, 1949), hydrogenation (Arveson, 1942), acetylation (Davis, 1970, 1971; Hayes and Wolff, 1957), alcohol fractionated (Julian and Iveson, 1958), acid/base hydrolyzed (Davis, 1970, 1971), blending (Wiesehahn, 1940), and oil free lecithin (Thurman, 1947), have been detailed in the patent literature. Enzymatic modification was patented by Pardun (1972) and reviewed by Schneider (2008). Pardun was an early pioneer in lecithin usage and held a number of patents (Pardun, 1967, 1969, 1970, 1972a, 1972b, 1972c). His bio can be found on the Lipid Library website (www.lipidlibrary.org). Buer (1913) was an early worker in the lecithin field, especially in the nutritional arena. An excellent review of the chemistry of phosphatides can be found in Deuel (1951). Jordan (1932, 1935, 1949) was also a pioneer in lecithin applications.

Bonekamp (2008) wrote an excellent review of the chemical modification of lecithins and Doig and Diks (2003) have reviewed methods for the modification of the lecithin headgroup. Only three major chemical reactions have seen industrial adaptation. These include acetylation by the reaction of acetic anhydride with the amino group of phosphatidylethanolamine, hydroxylation by reaction of hydrogen peroxide with double bonds of unsaturated phospholipids, and chemical/enzymatic modification cleaving the acyl group on the fatty acid chains with the formation of lysophosphatides (Arrigo and Servi, 2010).

A number of reviews have covered the food, industrial, and manufacturing uses of lecithin (Brian, 1976; Dashiell, 1989; Flider, 1985; Gunstone, 2009; Hernandez and Quezada, 2008; List, 1989; Orthoefer and List, 2006; Prosise, 1985; Schmidt and Orthoefer, 1985; Schipinov, 2002; Schneider, 2008; Sipos and Szuhaj, 1996; Stanley, 1951; Szuhaj, 1983, 2005; van Nieuwenhyzen, 1976, 1981, 2008; van Nieuwenhuyzen and Tomas, 2008; Wendel, 1995). The reader is directed to an early discussion of phosphatides containing nearly 200 references up to 1944 (Markley and Goss, 1944).

Liposomes in drug delivery systems were reviewed by Sharma and Sharma (1997), Immordino et al. (2006), and Mufamadi (2011). By 1991, well over 100 refereed publications on liposomes had been published. The classification, preparation, and applications of liposomes were recently reviewed by Akbarzadeh et al. (2013).

The lecithin industry is a mature one, but several factors have affected it. Although historically soybean has been the major source of lecithin worldwide, others are being sought because of increased demands for non-GMO (genetically modified organism) lecithin, including canola and sunflower (van Nieuwenhuyzen, 2014). Although lecithin from GMO soybeans has been shown to be equivalent to non-GMO lines (List et al., 1999), the European market prefers non-GMO lecithin. Over the past few decades, lecithin has become more important as a neutraceutical and food supplement ingredient. Moreover, the discovery of liposomes has provided a new and more efficient means for drug delivery. This chapter will review the lecithin industry, manufacture and properties of commercial products, their quality control and modification, and food and nonfood uses.

An Overview of the U.S. Lecithin Industry

The American lecithin industry is composed of over 30 companies who manufacture and/or sell a wide variety of products, including fluid bleached/unbleached, acetylated, hydroxylated, water dispersible (chemically or enzymatically modified), fluid identity preserved, fluid non-GMO, and granular and powdered deoiled products.

Virtually all food-grade lecithin produced in the United States is derived from soybeans and oil. A U.S. company in Florida offers soy, sunflower, and canola lecithin. U.S. production has remained fairly constant over the period from 1994 to 2010 (the last year for which statistics are available). Production has varied from a low of about 83,000 short tons in 1994 to a high of 112,000 short tons in 2003. The 17 year average is slightly over 98,000 short tons and amounts to an annual production of nearly 197 million pounds.

Manufacturing and distribution of specialized phospholipids and lecithin is global in scope, with a number of plants located in China, India, Croatia, Peru, Egypt, Sri Lanka, and Japan. China and India have 20 plants combined. In 2010, well over 100 countries imported lecithin/phospholipids. The top five include the Netherlands ($124.4 million), the United States ($65.7 million), Germany ($54.7 million), China ($45.3 million), and Italy ($38.8 million).

Worldwide, prices of lecithin vary widely depending in part of the degree of refining, source, and purity. High purity phosphatidylcholine (PC) from vegetable oils may sell for $5–10/kg up to over $1/gr. PC derived from eggs may sell for $15–100/kg up to $950–1000/kg. PC from soy extracts sell for around $20–30/kg. Very pure lyso PC may cost $740/gr or $800/500 gr. Soy-based lecithin sold in the United States is in the forms of fluid, granular, or modified. Although prices are not available, they vary with the degree of refining (in order of increasing costs): fluid, fluid single bleached, fluid double bleached, deoiled (95% AI), deoiled (97% AI), modified (acetylated, hydroxylated, chemically/enzymatically modified).

Soy-based fluid lecithin sold on the international market varies in price from $700–1200/ton in large lots. Imported prices range from $0.90–1/kg in Australia, $1/kg in South America, $2.07/kg in North America, and $3.50/kg in Europe and Japan.

Commercial Lecithins

Lecithins can be classified as fluid, oil-free, and modified. Gums from the treatment of crude oils (soybean, canola, sunflower) contain about 70% phospholipids and 30% oil and water. The lecithin is recovered by drying. Fluidization is accomplished by the addition of free fatty acids, metal salts, and/or oil. Specifications for fluid lecithin usually indicate a minimum of 62% acetone insolubles. Where color is important, lecithin may be bleached (Bollmann, 1929; Schwieger, 1934) via a...

Table of contents

• Cover image
• Title page
• Table of Contents
• Copyright
• Preface
• List of Abbreviations
• Chapter 1: Soybean Lecithin: Food, Industrial Uses, and Other Applications
• Chapter 2: Rice Bran Lecithin: Compositional, Nutritional, and Functional Characteristics
• Chapter 3: Sunflower Lecithin
• Chapter 4: Palm Phospholipids
• Chapter 5: Milk and Dairy Polar Lipids: Occurrence, Purification, and Nutritional and Technological Properties
• Chapter 6: Phosphatidylserine: Biology, Technologies, and Applications
• Chapter 7: Phenolipids as New Antioxidants: Production, Activity, and Potential Applications
• Chapter 8: Sugar Fatty Acid Esters
• Chapter 9: Production and Utilization of Natural Phospholipids
• Chapter 10: Autoxidation of Plasma Lipids, Generation of Bioactive Products, and Their Biological Relevance
• Chapter 11: Lysophospholipids: Advances in Synthesis and Biological Significance
• Chapter 12: NMR of Polar Lipids
• Chapter 13: Polar Lipid Profiling by Supercritical Fluid Chromatography/Mass Spectrometry Method
• Chapter 14: Omega-3 Phospholipids
• About the Editors
• Contributors
• Index