Omega 3 Fatty Acids

12 Key excerpts on "Omega 3 Fatty Acids"

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  Advanced Nutrition

  Macronutrients

  • (Author)
  • 2014(Publication Date)
  • Library Press

    (Publisher)

  ________________________ WORLD TECHNOLOGIES ________________________ Chapter- 10 Omega-3 Fatty Acid n −3 fatty acids (popularly referred to as ω−3 fatty acids or omega-3 fatty acids ) are a family of essential unsaturated fatty acids that have in common a final carbon–carbon double bond in the n −3 position ; that is, the third bond from the methyl end of the fatty acid. Nutritionally important n −3 fatty acids include α -linolenic acid (ALA), eicosapentaenoic acid (EPA), and docosahexaenoic acid (DHA), all of which are polyunsaturated. The human body cannot synthesize n −3 fatty acids de novo , but it can form long chain 20-carbon n −3 fatty acids (like EPA) and 22 -carbon n −3 fatty acids (like DHA) from the short chain eighteen-carbon n −3 fatty acid α -linolenic acid. The short chain n −3 fatty acids are converted to long chain forms (EPA, DHA) with an efficiency of approximately 5% in men, and at a greater percentage in women. These conversions occur competitively with n −6 fatty acids, which are essential closely related chemical analogues that are derived from linoleic acid. Both the n −3 α -linolenic acid and n −6 linoleic acid must be obtained from food. Synthesis of the longer n −3 fatty acids from linolenic acid within the body is competitively slowed by the n −6 analogues. Thus accumulation of long-chain n −3 fat ty acids in tissues is more effective when they are obtained directly from food or when competing amounts of n −6 analogs do not greatly exceed the amounts of n −3. History Although omega-3 fatty acids have been known as essential to normal growth and health since the 1930s, awareness of their health benefits has dramatically increased in the past few years. New versions of ethyl esterized omega-3 fatty acids, such as E-EPA and combinations of E-EPA and E-DHA, have drawn attention as highly purified and more effective products than the traditional ones.

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  Advanced Nutrition

  Micronutrients and Macronutrients

  • (Author)
  • 2014(Publication Date)
  • Academic Studio

    (Publisher)

  ________________________ WORLD TECHNOLOGIES ________________________ Chapter- 18 Omega-3 Fatty Acid n −3 fatty acids (popularly referred to as ω−3 fatty acids or omega-3 fatty acids ) are a family of essential unsaturated fatty acids that have in common a final carbon–carbon double bond in the n −3 position; that is, the third bond from the methyl end of the fatty acid. Nutritionally important n −3 fatty acids include α -linolenic acid (ALA), eicosapentaenoic acid (EPA), and docosahexaenoic acid (DHA), all of which are polyunsaturated. The human body cannot synthesize n −3 fatty acids de novo , but it can form long chain 20-carbon n −3 fatty acids (like EPA) and 22 -carbon n −3 fatty acids (like DHA) from the short chain eighteen-carbon n −3 fatty acid α -linolenic acid. The short chain n −3 fatty acids are converted to long chain forms (EPA, DHA) with an efficiency of approximately 5% in men, and at a greater percentage in women. These conversions occur competitively with n −6 fatty acids, which are essential closely related chemical analogues that are derived from linoleic acid. Both the n −3 α -linolenic acid and n −6 linoleic acid must be obtained from food. Synthesis of the longer n −3 fatty acids from linolenic acid within the body is competitively slowed by the n −6 analogues. Thus accumulation of long-chain n −3 fatty acids in tissues is more effective when they are obtained directly from food or when competing amounts of n −6 analogs do not greatly exceed the amounts of n −3. History Although omega-3 fatty acids have been known as essential to normal growth and health since the 1930s, awareness of their health benefits has dramatically increased in the past few years. New versions of ethyl esterized omega-3 fatty acids, such as E-EPA and combinations of E-EPA and E-DHA, have drawn attention as highly purified and more effective products than the traditional ones.

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  An Evidence-based Approach to Phytochemicals and Other Dietary Factors

  • Jane Higdon, Victoria J. Drake(Authors)
  • 2012(Publication Date)
  • Thieme

    (Publisher)

  183 20 Essential Fatty Acids (Omega-3 and Omega-6) Omega-3 and omega-6 fatty acids are polyun-saturated fatty acids (PUFAs), meaning they con-tain more than one cis double bond. 1 In all ome-ga-3 fatty acids, the first double bond is located between the third and fourth carbon atom count-ing from the methyl end of the fatty acid ( n -3). Similarly, the first double bond in all omega-6 fatty acids is located between the sixth and sev-enth carbon atom from the methyl end of the fatty acid ( n -6). Scientific abbreviations for fatty acids tell the reader something about their chem-ical structure. One scientific abbreviation for α-linolenic acid (ALA) is 18:3 n -3. The first part (18:3) tells the reader that ALA is an 18-carbon fatty acid with three double bonds, while the second part ( n -3) tells the reader that the first double bond is in the n -3 position, which defines it as an omega-3 fatty acid. Although humans and other mammals can synthesize saturated fatty acids and some mono-unsaturated fatty acids from carbon groups in carbohydrates and proteins, they lack the en-zymes necessary to insert a cis double bond at the n -6 or the n -3 position of a fatty acid. 1 Conse-quently, omega-6 and omega-3 fatty acids are es-sential nutrients. The parent fatty acid of the omega-6 series is linoleic acid (LA; 18:2 n -6), and the parent fatty acid of the omega-3 series is ALA ( Fig. 20.1 ). Humans can synthesize long-chain (20 carbons or more) omega-6 fatty acids, such as dihomo-γ-linolenic acid (DGLA; 20:3 n -6) and arachidonic acid (AA; 20:4 n -6) from LA and long-chain omega-3 fatty acids, such as eicosapentae-noic acid (EPA; 20:5 n -3) and docosahexaenoic acid (DHA; 22:6 n -3) from ALA (see the Bioavail-ability and Metabolism section below).

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  Health Foods from Ocean Animals

  • K. Gopakumar, Balagopal Gopakumar(Authors)
  • 2020(Publication Date)
  • CRC Press

    (Publisher)

  HAPTER 4

  Omega 3 Fatty Acids: THEIR ROLE IN HUMAN NUTRITION

  4.1      WHAT ARE OMEGA-3 FATTY ACIDS?

  For naming fatty acids in 1953 a new biochemical system of nomenclature was suggested replacing the old Geneva system. According to the new system the unsaturated bonds are numbered with reference to terminal methyl group instead of numbering from the functional group, -COOH. The terminal group is notated as ω (omega) the last Greek letter. The terminal methyl group is numbered 1. The term omega-3 indicates that the first double exists in the 3rd carbon atom with respect to the terminal methyl group (ω)of the long carbon chain unsaturated fatty acid. According to this scheme 4 main families of unsaturated fatty acids are established. For example, Linolenic acid earlier called Alpha- Linolenic acid (ALA), 18:3, is now notated as 18:3 ω 3, meaning there are 18 carbon atoms in the fatty acid, 3 double bonds and the first double bind exists in the 3rd carbon atom with respect to the terminal methyl group(ω). According to this classification, 4 main families of unsaturated fatty acids are established. They are (Fig. 12 ):

  Fig. 12 . Families of polyunsaturated fatty acids

  Table 7 . Unsaturated fatty acid families

  ω-3 Unsaturated	ω-6 Unsaturated	ω-7 Unsaturated	ω-9 Unsaturated
  α-Linolenic (18:3)	Dihomo-γ-linolenic (20:3)	Vaccenic (18:1)	Gondoic (20:1)
  Stearidonic (18:4)	Arachidonic (20:4)	Paullinic (20:1)	Erucic (22:1)
  Eicosapentaenoic (20:5)	Adrenic (22:4)	Oleic (18:1)	Nervonic (24:1)
  Docosahexaenoic (22:6)	Osbond (22:5)	Elaidic (trans-18:1)	Mead (20:3)
  Palmitoleic (16:1)
  γ-Linolenic (18:3)

  Biologically important unsaturated fatty acids

  Fig. 13 : Unsaturated fatty acid

  There are 11 omega-3 fatty acids identified existing in nature. They are listed below:

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  The Role of Alternative and Innovative Food Ingredients and Products in Consumer Wellness

  • Charis M. Galanakis(Author)
  • 2019(Publication Date)
  • Academic Press

    (Publisher)

  Stark et al., 2016 ).

  Fatty acids are separated into three classes—saturated, unsaturated, or polyunsaturated fatty acids (PUFAs)—according to the presence and number of double bonds in their chemical structures (Nabavi et al., 2015 ). Omega-3 (ω-3) and omega-6 (ω-6) represent two distinct families of PUFAs containing 18–22 carbons (Mori, 2017 ). The position of the first double bound in the carbon chain, as counted from the methyl terminus, characterize the classification of “omega”; that is, whether it is ω-3 or not. The most important LC-PUFAs are ω-3, which is characterized by the presence of the first double bond (C C) at the third carbon atom. Ω6 and ω3 fatty acids derive from linoleic acid (LA; 18: 2ω6) and α-linolenic acid (ALA; 18: 3ω3), respectively (Mori, 2017 ). ALA is the simplest ω3 fatty acid, which is synthesized from LA by desaturation. These two fatty acids cannot be synthesized in humans and need to be obtained through diet, since they are termed as “essential fatty acids”. Although EPA and DHA can be synthesized from ALA in the human body, it is an inefficient process with a poor yield (Burdge and Calder, 2005 ; Domenichiello et al., 2015 ). Therefore, adequate levels of EPA and DHA should be obtained from marine sources (Anderson and Ma, 2009 ). There are several microorganisms which can produce omega-3 PUFAs with a chain length above C20, such as lower fungi, bacteria, and marine microalgae (Bajpai et al., 1991 ; Kendrick and Ratledge, 1992 ). The most promising microorganisms for the production of omega-3 PUFAs seem to be the marine microalgae, as they are able to accumulate high amounts of omega-3 PUFAs. The advantage of algae oil compared with fish oil is thus that the oil contains higher levels of, in particular, DHA than fish oil, e.g., up to 52% (Sijtsma and de Swaaf, 2004 ). Cold-water oily fish such as salmon, herring, mackerel, anchovies and sardines are the most widely available sources of EPA and DHA (Bolles and Begg, 2000

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  Sports Nutrition

  Fats and Proteins

  • Judy A. Driskell(Author)
  • 2007(Publication Date)
  • CRC Press

    (Publisher)

  After considerable scientific information, the National Academy of Science’s Insti- tute of Medicine released the Dietary Reference Intakes for Adequate Intakes for linoleic acid and α -linolenic acid for the first time in 2002. Important information is now available about the risk of excessive ω -3 and ω -6 fatty acids intake; however, upper limit intakes have not yet been set. In that regard, although some studies have explored the effects of these polyunsaturated fatty acids on athletes, there is still not enough information to set requirements for individuals engaged in exercise, and more research is needed in that area. Research may focus on supplementation to enhance aerobic performance and to decrease exercise-induced bronchoconstriction in athletes. This chapter provides current information on the properties, metabolism, func- tions, nutrient status assessment, recommended intakes, and other important char- acteristic of ω -3 and ω -6 fatty acids. In addition, available scientific information on the effects of ω -3 and ω -6 fatty acids supplementation on physical performance and exercise is presented. 4.2 CHEMICAL STRUCTURES AND SYNTHESIS Fatty acids are hydrocarbon chains with a carboxyl group (–COOH) at one end and a methyl group (CH 3 ) at the other. Fatty acids vary in chain length, degree of unsaturation, 1 and location of double bonds 2 and can be classified as saturated (no double bonds), monounsaturated (single double bond), and polyunsaturated (several double bonds). Unsaturated fatty acids can be classified in two different ways: the delta ( Δ ) and the omega ( ω ) numbering system. 1,3 In the delta system, the carboxyl carbon is denoted as carbon 1, while in the omega system carbon 1 is the methyl carbon. 3 The number of double bonds in the fatty acid chain are counted from either the carboxyl or the methyl end.

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  Biochemistry and Health Benefits of Fatty Acids

  • Viduranga Waisundara(Author)
  • 2018(Publication Date)
  • IntechOpen

    (Publisher)

  11 Chapter 2 Fatty Acids: From Membrane Ingredients to Signaling Molecules Michio Hashimoto and Shahdat Hossain Abstract Fatty acid constitutes the foundation cell membranes, provides metabolic energy, affects functions of membrane-bound enzymes/receptors, conducts signaling cascades, and helps in learning-related memory cognition in mammals, including humans. Structurally, the fatty acids are of two kinds: saturated and unsaturated; the latter are again of mono- and polyunsaturated types. From nutri-tional perspectives, they are of essential and nonessential types. Omega-6 linoleic acid ( ω -6 LLA, C18:2) and ω -3 alpha linolenic acid ( ω -3 α LLN, C18:3) and ω -6 ara-chidonic acid [( ω -6 AA, C20:4); it is conditional] are essential fatty acids (EFAs). In addition, mammalian brains cannot biosynthesize the ω -3 docosahexaenoic acid ( ω -3 DHA, C22:6) in adequate amounts because of lack of necessary enzymes. Thus, DHA is essential for the growth and development of the brains. Deficiency of DHA produces visual- and learning-related memory impairments, and neurodegen-eration in the aged brains and Alzheimer’s disease brains. Finally, this chapter will highlight and broaden the awareness about the essentiality of different fatty acids with a special emphasis on DHA. Keywords: docosahexaenoic acid, eicosapentaenoic acid, arachidonic acid, alpha-linolenic acid and linoleic acid, eicosanoids, docasonoids, brain cognition 1. Introduction The concept of fatty acid was first introduced by the French chemist Michel Eugène Chevreul as graisse acide (acidic fat) [1]. Fatty acids are chemically defined as carboxylic acids with either saturated or unsaturated aliphatic chains and are derived after hydrolysis of fats or oils. A fatty acid has, therefore, an acid group at one end of its molecule and a methyl group at the other end [2, 3].

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  Fats and Associated Compounds

  • Jose Manuel Miranda Lopez, Alberto Cepeda Saez, Jose Manuel Miranda Lopez, Alberto Cepeda Saez(Authors)
  • 2021(Publication Date)
  • Royal Society of Chemistry

    (Publisher)

  Chapter 6 Essential and Omega-3 Fatty Acids in Human Health

  J. M. Mirandaa , A. C. Mondragóna , S. Ramirez-Montes,b , I. S. Ibarra,b , E. M. Santos,b , A. Lamasa , L. Sinisterra-Lozaiaa and A. Lopez-Santamarinaa

  a Departamento de Química Analítica, Nutrición y Bromatología, Facultad de Veterinaria, pabellón IV, planta baja, campus Universitario s/n, Universidad de Santiago de Compostela, Spain;

  b Area Academica de Quimica, Universidad Autonoma del Estado de HidalgoCarr. Pachuca-Tulancingo km 4.5, 42184 Pachuca, Hidalgo, Mexico Email: [email protected]

  6.1 Introduction

  The nutritional value and human health benefits of some dietary fats were undervalued over a long period of time, by considering all dietary fats to be only an energy source for the human body. It was not until the end of the 1920s that the scientific community began to become aware of the need for certain fat components for the proper maintenance of health. This discovery was made by George Oswald Burr at the University of Minnesota.1 He observed that laboratory rats fed a diet totally devoid of fat developed a deficiency-type disease and consequently concluded that some components of fat were an essential dietary component, the lack of which could cause important syndromes in these animals.

  Since then, large amounts of scientific research activity concerning essential fatty acids has been carried out. According to the Scopus® database, the number of scientific articles including “essential fatty acids” in the filed “title, abstract or keywords” increased from 1 in 1930 to 2032 in 2020 (Figure 6.1 ). Nowadays, both α-linoleic acid (ALA) and linoleic acid (LA) are considered to be essential fatty acids (EFA) in the human body, because the human body cannot synthesize them de novo . This is because humans lack the enzymes to introduce double bonds in fatty acids beyond carbons 9 and 10 as counted from the carboxylic acid end.2 In addition to ALA and LA, usually it is considered that arachidonic acid (ARA), a fatty acid usually obtained from dietary animal sources, is also an essential fatty acid,2 because ARA is converted into different important compounds by the sequential action of various enzymes. After ingestion in the form of dietary triglycerides and absorption in the intestine, EFA can follow different routes into the mammal's body. They can be used to provide energy by β-oxidation, can be esterified into cellular lipids, or can be desaturated and esterified to form n -3 or n -6 PUFA series, mainly in the liver, but can also occur in other tissues.3

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  Fats and Oils in Health and Nutrition

  • Khetarpaul, Neelam(Authors)
  • 2021(Publication Date)
  • Daya Publishing House

    (Publisher)

  2 : 1 serving 85 g (3 oz) cooked portions. Source : Gebauer et al. (2006). Studies on Role of Omega-3 Fatty Acids in Health and Disease As conversion from ALA to EPA and DHA is limited, fish, particularly fatty fish, is a source of the long-chain omega-3 polyunsaturated fatty acids (PUFAs) eicosapentaenoic acid and docosahexaenoic acid. Therefore, individuals who do not eat fish or fish oils (e.g, vegans and non-fish-eating vegetarians and meat-eaters) could be at risk of low or inadequate n-3 PUFA This ebook is exclusively for this university only. Cannot be resold/distributed. status. Various aspects of omega-3 fatty acids through consumption of fish or fish oil and their therapeutic effects have been discussed as under. I. Cardiovascular Disease (CVD) Since the first cross-cultural epidemiologic studies conducted in the 1970s, evidence has been accumulating regarding the role of n–3 polyunsaturated fatty acids in fish (EPA and DHA) in the prevention and management of cardiovascular disease (CVD). α-Linolenic acid (ALA), a plant-derived n–3 fatty acid and a precursor to EPA and DHA (found in walnuts and certain vegetable oils such as flaxseed, canola and soybean), is also of interest for CVD prevention. The AHA Scientific Statement reported by Kris-Etherton et al . (2002) had addressed distinctions between plant-derived (α-linolenic acid, C18:3n-3) and marine-derived (eicosapentaenoic acid, C20:5n-3 [EPA] and docosahexaenoic acid, C22:6n-3 [DHA]) omega-3 fatty acids. Evidence from prospective cohort studies in generally healthy populations and randomized controlled trials (RCTs) in patients with known coronary heart disease suggest that the n–3 polyunsaturated fatty acids in fish are likely to prevent sudden cardiac death, manifested as fatal ischemic heart disease or arrhythmic death (Lemaitre et al., 2003; Siscovick et al., 1993; Albert et al., 1998; Mozaffarian and Rimm, 2006) and possibly as ischemic stroke (Mozaffarian et al., 2005).

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  Health Effects of Polyunsaturated Fatty Acids in Seafoods

  • Artemis P Simopoulos(Author)
  • 2012(Publication Date)
  • Academic Press

    (Publisher)

  PART II. THE IMPACT OF OMEGA-3 FATTY ACIDS ON EICOSANOID FORMATION This page intentionally left blank CHAPTER 2 THE FATE OF POLYUNSATURATED FATTY ACIDS 1 William E.M. Lands Department of Biological Chemistry University of Illinois at Chicago Chicago, Illinois I. INTRODUCTION Several considerations are involved w h e n we place polyunsaturated fatty acids (PUFAs) in our diets: 1. They can replace saturated fatty acids. 2. They can decrease the synthesis of saturated fatty acids. 3. They can decrease levels of circulating lipoproteins. 4. They can influence the synthesis of eicosanoids. High levels of circulating lipoproteins may be a risk factor c o m m o n to several diseases, and excessive eicosanoid formation may be an element common to many disorders. The polyunsaturated fatty acids in fish oil can influence all of the events listed above. The first three events may occur with any dietary unsaturated fatty acid (e.g., see Mattson and Grundy, réf. 1), and customary dietary advice has tended to recommend the inges-tion of unsaturated fatty acids without specifying the chemical structure (ω —3, ω —6, or ω -9 ) of the unsaturated acid. The studies of the greater effectiveness of the ω —6 acids relative to the ω -3 acids as essential nu-^his work was supported by grants from the U.S. Public Health Service (HL34045, GM30509, and GM31494), the E.M. Bane Estate Trust (University of Illinois at Chicago), and a fellowship from General Mills, Inc. Health Effects of Polyunsaturated Fatty Acids in Seafoods 33 Copyright © 1986 by Academic Press, Inc. All rights of reproduction in any form reserved. 34 William E. M. Lands trients (2,3), and the ineffectiveness as prostaglandin precursors of the ω - 3 acids relative to the ω -6 acids (4,5), set the stage for a careful comparison of the fate of these two types of polyunsaturated fatty acids.

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  Introduction to Clinical Nutrition

  • Vishwanath Sardesai(Author)
  • 2011(Publication Date)
  • CRC Press

    (Publisher)

  69 4 Role of Essential Fatty Acids 4.1 FATTY ACIDS Fatty acids are chains of covalently linked carbon atoms, bearing hydrogen atoms, which termi-nate in a carboxylic group that is responsible for their properties as acids. The naturally occurring fatty acids are, for the most part, unbranched and acyclic, but complex structures with branched or cyclic chains do occasionally occur, particularly in lower biological forms. The total number of carbon atoms in a molecule is usually even although fatty acids containing odd-numbered car-bon atoms also are found in nature. They have the basic formula CH 3 [CH 2 ] n COOH, where n can be any number from 2 to 22 and is usually an even number. One method of classification of fatty acids is according to their chain length (i.e., the number of carbon atoms they contain). Fatty acids containing 2–4 carbon atoms are called short-chain fatty acids, while those with 6–10 and 12–24 carbon atoms are called medium-chain and long-chain fatty acids, respectively. Fatty acids can also be classified according to the number of double bonds between the carbon atoms (i.e., the degree of saturation): saturated, with no double bonds; unsaturated, with one double bond; and polyunsaturated fatty acids (PUFAs), with two or more double bonds. Fatty acids with two, three, four, five, and six double bonds are called dienoic, trienoic, tetraenoic, pentaenoic, and hexaenoic, respectively. The carbon atoms of the fatty acids are numbered from the carboxyl group ( Δ numbering system) or lettered (W or n numbering system): numbering system (carboxyl side) CH 3 16 4 3 2 1 (CH ) CH CH CH COOH 1 13 14 15 16 W or number 2 11 2 2 2 n ing system (W-side) Fatty acids are abbreviated in the Δ nomenclature by listing the carbon number and position of double bonds (C a Δ b ). Thus, palmitic acid is abbreviated as C 16 :0 or C 16 :0 Δ 0 , and palmitoleic acid as C 16 :1 or C 16 :1, Δ 9 .

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  Guide to Nutritional Supplements

  • (Author)
  • 2009(Publication Date)
  • Academic Press

    (Publisher)

  In addition, fatty acids and their coenzyme A derivatives have many metabolic regulatory roles. Fatty-Acid Nomenclature Conventions In this article, fatty acids will be identified by their chain length, the number of double bonds present, and the position of the first double bond from the methyl end of the molecule. Thus 14:0 denotes a saturated fatty acid with 14 carbon atoms, 16:1 n -9 denotes a monounsaturated fatty acid with 16 carbon atoms in which one double bond occurs nine carbon atoms from the methyl end, and 20:4 n -6 denotes a polyunsaturated fatty acid with 20 carbon atoms in which the first of four double bonds is found six carbon atoms from the methyl end. Unless otherwise noted, all double bonds are in the cis configuration and double bonds in polyunsaturated fatty acids are separated by a single methylene (–CH 2 –) group. The car-boxyl carbon atom of any fatty acid is carbon-1. The adjacent carbon atom is referred to as either carbon-2 or the -carbon; the next is carbon-3 or the -carbon, and so on. Some examples are shown in Figure 1 . Physical Properties of Fatty Acids Fatty acids are aliphatic organic acids with the fundamental structure CH 3 (CH 2 ) n COOH, where n can range from zero to more than 26. Thus, fatty acids range from the shortest, acetic acid (2:0), to the very long-chain fatty acids containing 26 or more carbon atoms (e.g., 26:0). Although fatty acids with an odd number of carbon atoms exist in nature, most common fatty acids have an even number. The most abundant fatty acids in human lipids and in dietary lipids are the long-chain fatty acids 16:0 (palmitic acid) and 18:1 n -9 (oleic acid) ( Figure 1 ). The hydrophobic nature of the hydrocarbon chain of fatty acids containing more than eight carbon atoms renders them quite insoluble in aqueous media. It has been estimated that for every two additional carbon atoms in the fatty-acid chain its solubility decreases 10-fold.

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