Food Analysis
`
`RIMFROST EXHIBIT 1177 Page 0001
`
`af) Ame)
`Leo M. L. Nollet
`
`
`
`RIMFROST EXHIBIT 1177 Page 0001
`
`Volume I thru 3
`
`Handbook of
`
`second Edition, Revised and Expanded
`
`Physical Characterization and Nutrient Analysis
`
`
`
`
`
`

`

`Handbook of
`
`Food Analysis
`
`Second Edition
`
`Physical Characterization and Nutrient Analysis
`
`edited by
`Leo M.L. Nollet
`Hogescholl Gent
`Ghent, Belgium
`
`(c#*) CRC Press
`
`(ORC Prost an imprint of tian
`Taylor fi Framcis ‘(Groupam informa iui
`
`
`
`
`
`RIMFROST EXHIBIT 1177 Page 0002
`RIMFROST EXHIBIT 1177 Page 0002
`
`

`

`Whe first obbon of thos book was published as the Handbwekt of Fowd Anolpsis: Fotos J ond 2
`
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`
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`
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`
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`RIMFROST EXHIBIT 1177 Page 0003
`RIMFROST EXHIBIT 1177 Page 0003
`
`

`

`9 F
`
`atty Acids
`
`Rosario Zamora and Francisco |. Hidalgo
`fnctituie de fa Grose, (SC, Seville, Spain
`
`L
`
`INTRODUCTION
`
`Lipids consist of a broad group ofcompounds that are
`generally soluble in organic solvents but only sparingly
`soluble in water. They are major constitucnts of
`adipose tissuc, and together with proteins and carbo-
`hydrates, they constitute the principal structural com-
`ponents ofall living cells. Glycerol caters of fatty acids,
`which account
`for about 98% of the lipids in our
`foods and over 90% of the fai
`in the body, have
`been traditionally called fais and oils, based solcly
`on whether the material is solid of liquid at room
`temperature (1-1).
`Food lipids are cither consumed in the form of
`isolated fats or as constitucnis of basic foods.
`Worldwide,
`food lipids’
`intake warics considerably
`from some countrics to others. In general, the con-
`sumplion of food lipids increases with increasing per
`capita income. Thus,
`in developing countrics food
`lipids’ intake is, and has been for many gemeralions,
`10 to 20%. of the energy intake, while in developed
`countnics dictary food lipids’ intake ranges from 35 to
`45% of the total energy intake (4-8).
`Fatty acids are key componcnis of lipids. They arc
`the aliphatic monocarboxylic acids that can be liber-
`ated by hydrolysis from naturally occurring fais.
`Although more than 1000) acids have been identified,
`the number oocurring frequently in most common
`lipids is much fewer than this and most food analysts
`will probably encounter not more than a few tens of
`different acids.
`
`IL STRUCTURE, OCCURRENCE, AND
`PROPERTIES
`
`A. Chemical Structure
`
`Because fatty acids are made biosynthetically from a
`limited number of substrates by a limited number of
`pathways certain sirwctural features recur frequently.
`Thus, moet fatty acids are straight-chain compounds
`with an cven oumber of carbon atoms in cach
`molecule. This chain may have double bonds, which
`has commonly # (eis) configuration, and, in the casc
`of several double bonds,
`these are usually separated
`by one methylene group. All
`these general conclu-
`sions hawe execplions and branched,
`trans, and con-
`jugaied fatty acids may be found to some extent
`in
`most foods.
`In addition, substituted acids are rare,
`but natural hydroxy, cpoxy, and oxo acids have been
`described.
`Fatty acids are classified according to their chain
`length, the existence and the number of double bonds,
`and the presence of branches, cycles, or other groups.
`There is not a generally accepted division of fatty
`acids according to chain length, although shori-chain
`fatty acids are usually considered having from 4 to
`10 carbon atoms; moedium-chain fatty acids, 12 or 14
`carbon atoms; and long chain fatty acids, 16 or more
`carbon atone.
`The following sections will give an overview of the
`Moat significant charactecriatica of the different types of
`fatty acids that can be found in foods. It is out of the
`scope of this chapter to present an exhaustive review of
`
`221
`
`
`
`
`
`
`RIMFROST EXHIBIT 1177 Page 0004
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`

`

`zzz
`
`the different clasecs of Patty acids. Tt can be found
`cekewhere (sec, for cxample, Ref. 8-14).
`
`1. Unbranched Saturated Fatty Acids
`Unbranched, straight-chain molecules with an cven
`number of carbon atoms arc dominant among the
`saturated fatty acids (Table |). These acids are present
`in a high content in animal fats and in some wegetable
`fata such as palm and coconut oils. Medium- and
`short-chain fatty acids are triacylglycerol constitucnis
`in the fat and oil of milk, coconut, and palmaced. Fatty
`acids with odd numbers of carbon atome arc preacniin
`food only in traces (Table 2).
`
`2. Unbranched Unsaturated Fatty Acids
`The unsaturated fatty acids, which arc major conali-
`tucnts of lipids, contain one or more allyl groups in
`their chains. The naturally occurring unsaturated fatty
`acids in fats are almost exclusively in the ecis-form,
`although tran-acids arc abundant in ruminant milk
`fais and in the catalytically hydrogenated fais (17,18).
`In ruminant milk fats, these trons bonds, which may
`constitute about 10% of total unsaturated fatty acids,
`result
`from microbial action in the rumen where
`polyunsaturated fatty acids of the feed are partially
`hydrogenated.
`In the monounsaturated fatty acids, one double
`bond is present in the aliphatic chain (Table 3). Its
`position is determined from the carboxyl cmd (sys-
`tematic and A numbering) or from the methyl end (A
`or a numbering). Thus, for example, palmitoleic acid
`or 4 )-hexadecenoic acid, according to the systematic
`name, is reprcacnied by the numeric symbol 1] A9 or
`loc] a-7. Unless otherwise indicated, the double bond
`has ci configuration.
`The structural relationship that cxisis among wnsa-
`turated fatty acids derived from a common biosyn-
`thetic pathway is better understood when fatty acids
`with the same oecthyl ends are combined into prowps.
`This is because organisms lengthen fatty acid chains by
`adding carbons at the acid cnd of the chain. Using the
`fora sysiem, four family groups of unsaturated fatty
`acids can be distinguished: v-3, a-h, a-7, and m9
`(Table 4). In plants the most widespread methylene-
`interrupted polyene fatty acids are linoleic acid (18:2
`A912) and o-linolenic acid (18:35 49,132,105), which are
`the origin of the #-@ and a-3 familics, reepectively. The
`paeacnec of these two fatty acids in foods is of great
`importance since they cannot be synthesized de novo
`by human and animal tissucs and should thereby be
`provided with the dict. On the other hand, polyenes of
`
`famoru amd Hidalkpo
`
`the a-7 and #-9 familics, derived from palmitoleic (16:1
`AQ) and oleic (18:1 A9) acids, respectively, are rarcly
`encountered in animal food, except when animals arc
`deficient
`in cescntial
`fatty acids (presence of 203
`ASBAT).
`
`(OMther Fatty Acids
`3.
`Tn plant and animal food, leas common fatty acids may
`be preacnt. Thus, short-chain, odd-numbered, and
`branched-chain fatty acids are preacnt
`in ruminant
`milks and their derivatives. The most common type of
`branching isa single methyl group at the positions a-2
`(ise acids) or a-3 (anteise acids). Acids with more than
`one methyl growp generally have them attached to even
`carbon atoms. Hydroxylated fatty acids can be found
`Principally in plant
`lipids. Other oxygenated fatty
`acids, epoxy and keto fatty acids, are usual compo
`ments of several seed oils. Conjugated, allenic, and
`acetylenic fatty acids do not occur to any significant
`extent
`in food lipids. Cyclic fatty acids are usual
`componcnis of seweral seed oils. Thus, the cyclopro-
`pene fatty acids, malvalic and sicrculic, arc found in
`noticeable amounts in baobab and kapok seed oils and
`in trace amounts in cottonseed oil. They are frequently
`accompanied by cyclopropanc fatty acids. Other
`oxygenated and cyclic acids arc formed in certain
`amounis when polyunsaturated fatty acids arc oxidized
`or heated at relatively high temperature (19). More
`detailed information regarding these unusual dictary
`fatty acids can be obtained from specialined books
`(10,12).
`
`B. Occurrence
`
`In general, the following outline of fatty acid composi-
`tion can be given:
`
`© Depot fate of higher land animals consist mainly
`of palmitic, oleic, and stearic acids and arc high
`in saturated fatty acids (Table 3). The total
`content of acids with 18 carbon atoms is about
`70%. Mewertheless,
`the kind of feed consu-
`med by the animals may greatly influence the
`composition of the depot fais.
`* Ruminant milk fats are characterized by a much
`greater
`varicty of component
`faity acids
`(Table 3). Many fatty acids have been identified
`in different studics, and about 15 of the fatty
`acids occur in quandtitics of 1% or more of the
`total fatty acids. Shon saturated acids with 4 to
`10 carbon atoms are present in relatively large
`amounts, The major fatty acids are palmitic,
`
`
`
`
`
`
`
`
`RIMFROST EXHIBIT 1177 Page 0005
`RIMFROST EXHIBIT 1177 Page 0005
`
`

`

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`RIMFROST EXHIBIT 1177 Page 0006
`RIMFROST EXHIBIT 1177 Page 0006
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`RIMFROST EXHIBIT 1177 Page 0007
`RIMFROST EXHIBIT 1177 Page 0007
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`RIMFROST EXHIBIT 1177 Page 0008
`RIMFROST EXHIBIT 1177 Page 0008
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`RIMFROST EXHIBIT 1177 Page 0009
`RIMFROST EXHIBIT 1177 Page 0009
`
`

`

`Fally Acids
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`RIMFROST EXHIBIT 1177 Page 0010
`RIMFROST EXHIBIT 1177 Page 0010
`
`

`

`ze
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`Table 5 Pally Acd Composition of Schocted Land Anomals Fails”
`Boel fat
`Chicken Fat
`Limb (at
`
`Land
`
`Milk fat
`
`Pork. fat
`
`Tallorw
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`4:0
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`11
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`17:
`17:
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`20:1
`20a
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`05
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`03
`
`38
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`62
`
`140
`424
`24
`17
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`“Patty acid compositions areexpressed as mean average weight per cent composition oma fattyacid basis. Patty acids presentin bess than 6.1% of
`the total bawe been cockeded.
`Abbreviations: a, aged branched fatty acid; i, iv bramched fatty acid.
`ouree: Adapted fromm Piels. 2) 24.
`
`oleic, and stearic, According to Jensen and
`Newburg (22) 400 fatty acids hawe been found
`Prcacnt in cow's milk fat. They include even and
`odd saturated acids from 20 to 2890; cwen and
`odd monecnoic acids from 10:1 to 262), with the
`exception of 11:1, and including positional and
`geometric isomers; even unsaturated fatty acids
`from 14:2 to 26:2 with some geometric isomers;
`polyenoaic even acids from 18:3 to 72:6 including
`some conjugated trans isomers; monobranched
`fatty acids 9:0 and 110 to 25:0 (some iso and
`some diteie); multibranched acids from 1600
`to THO, beth odd and even with three to five
`methyl branches; and to clowe
`the list, a
`number of keto, hydroxy, and cyclic acids.
`
`=.
`
`Marine oils also contain a wide variety of fatty
`acids (Tabke 6) Ackman (25) has reported as
`many as 50 or 60 components, although only
`about 14 of theac are of importance in terms of
`weight per cent of the total. They are low in
`saturated fatty acids (mainhy myristic and palmi-
`tic acids) and high in unsaturated fatty acids,
`cepecially those unsaturated acids with long
`chains containing 20 of 22 carbons of more and
`up to six double bonds.
`Fruit coat fats contain mainly palmitic, olic,
`and sometinecs linoleic acids.
`Seod fais can be divided into three groups on the
`hasis of fatty acid composition (Table 7). The
`first group comprises oils containing mainly
`
`
`
`RIMFROST EXHIBIT 1177 Page 0011
`RIMFROST EXHIBIT 1177 Page 0011
`
`

`

`Fally Acids
`
`Table @ Patty Acid Composion of Depot Pats from Selected Fishes*
`
`140
`14:1
`Téciey
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`16
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`164 vl
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`1k:3 93
`1h-4 03
`190
`ah
`21
`22 ni}
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`20:3 93
`2k 93
`25 93
`21:5 az
`220
`22:1
`224 93
`2241 nf
`22:5 93
`22:5 fh
`22:6 93
`0
`24:1
`
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`7A
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`o4
`Oi
`174
`a0
`02
`10
`22
`24
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`1
`12
`08
`03
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`6.7
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`O.5
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`13
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`2A
`10
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`12
`194
`11
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`1.1
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`6.7
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`11
`15
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`6.3
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`0.9
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`0.9
`Ta
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`Ruonbow trout
`20
`a1
`
`3
`178
`i.
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`fit
`1h
`
`44k
`325
`143
`
`03
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`2
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`13
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`03
`10.3
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`24
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`1.7
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`
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`1.1
`26
`0.6
`a
`
`“Pattyachd compnsitions are expressed a; mean average weight per cemt composition om a fatty acd hasis. Patty acids present in less than dl. 1% of
`the total awe been cockeded.
`Abbreviation: b, branched fatty acid.
`Soaree: Adapted from Ptells. 202435.
`
`18 carbon atoms and
`fatty acids with 16 of
`includes most of the seed oil. In this group
`arc cottonaced oil, peanut oil, sunflower oil,
`com oil, sesame oil, olive oil, palm oil, soybean
`oil,
`and
`saMower oil, The second group
`comprises scod oils containing erucic acid (22:1
`AIS). These include rapeseed and mustard aced
`
`oils. The third group is that ofthe vegetable fats,
`comprising coconut ofl and palm kernel oil,
`which are highly saturated, containing large
`amounts of medium- and short-chain fatty
`acids, and cocoa buiter, which is hard and britth
`al room temperature and contains only palmitic,
`stearic, and oleic acids in approximately equal
`
`
`
`
`
`RIMFROST EXHIBIT 1177 Page 0012
`RIMFROST EXHIBIT 1177 Page 0012
`
`

`

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`RIMFROST EXHIBIT 1177 Page 0013
`RIMFROST EXHIBIT 1177 Page 0013
`
`
`
`
`
`

`

`Fally Acids
`
`In addition, plant breeding pro-
`proportions.
`grams are producing new seeds with changed
`fatty acid composition.
`
`C. Physical Properties
`
`i. Polymorphism
`Polymorphism is defined as the ability of a chemical
`compound to form different crystalline or liquid
`crystalline structures. The melting and crystallization
`behavior will differ from one polymorph to another
`(27). Depending on the method by which they arc
`obtained,
`the cewen-numbered saturated fatty acids
`can crystalline in any of the polymorphic forme. In
`decreasing length of long spacings (or increasing tilt of
`the chains), these are designated A, B, and C, the C
`form being the stable crystal form with the highest
`melting temperature. Similarly,
`the acids with odd
`numbers of carbon atoms arc designed A’, B’, and
`(. The A and A’ forms have triclinic subcell chain
`packing,
`the remaining forms are packed in the
`common orthorhombic manner. Differences in crystal
`forms were also obeerved with branched and poly-
`unsaturated fatty acids (28,29).
`
`2. Melting Point
`As usual in homologous series, the melting point of the
`saturated fatty acids (Tables | and 2) increases with
`chain length. However, the melting curve of the even
`members occurs at higher temperature than the curve
`formed by the odd fatty acids, particularly for the
`short-chain fatty acids. Theac differences can be
`explained by the crystal structure of the C and
`forms duc to differences in the packing of the methyl
`cnd groups. A dense packing is achieved in the C form
`of the even saturated fatty acids.
`For unsaturated fatty acids (Tables 3 and 4) there is
`a reduction in the melting point compared to the cor-
`reaponding saturated fatty acids, and the higher the
`number ofdouble bonds the higher the decrease for the
`same chain lengih. The melting point also depends on
`the position of the dowble bonds. In monocnes, it
`is
`lower when the dowhle bond is near to the carboxyl
`group, increasing swocessively toward the methyl end.
`The presacnee of a rane doubk bond increases the
`melting point when compared to the «ix isomer.
`
`3. Boiling Point
`The boiling point of the even saturated fatty acids
`(Table |) increases with chain length. The boiling curve
`
`231
`
`of the odd members (Table 2) is below that of the even
`fatty acids. The preacnoe of a cis double bond slightly
`decreascs the boiling point, and this cffect imercascs
`with the unsaturation. The boiling point of the methyl
`esters is markedly lower than that of the free fatty
`acids. This property is widely used in the analysis of
`long-chain fatty acids by gas liquid chromatography.
`
`4. Solubility
`The solubility of fatty acids in water is generally low
`because of the hydrophobicity of the aliphatic chain in
`relation to the number of carbon atoms. The solubility
`increases with decreasing chain length.
`In addition,
`even and odd fatty acids follow the same curve of
`solubility in water, not showing alicrnation. The solu-
`bility increases slighily with the presence of double
`bonds and with the temperature.
`The solubility of fatty acids in organic solvents is
`relatively high and increases with temperature. In theac
`solvents, even and odd fatty acids alternate, the latier
`being more soluble. Methyl caters of fatty acids are
`more eoluble, in organic solvents, than free fatty acids.
`This property is useful in the analysis of fatty acid
`mecthyl esters by gas and liquid chromatography.
`
`S&S. Other Properties
`Other physical characteristics of fatty acids will not be
`described in this section. Information regarding den-
`sity, viscosity, refractive index, surface tension, and
`diclectric constant are reported in specialized books
`(28-31).
`
`D. Chemical Properties
`
`The chemical propertics offatty acids arc related cither
`to the carboxyl group or to the hydrocarbon chain.
`
`Ll. Reactions of the Carboxyl Group
`From an analytical point of view, one of the most
`important
`reactions of fatty acids is caterification,
`becauac fatty acid caters arc broadly employed for
`chromatographic analyses. Esters can be formed from
`carboxylic acids and alcohols cither directly, by
`transforming the acid inte a more reactive derivative,
`or by activating the aleohol
`for condensation with
`the carboxylate (32,33). The direct csicrification of a
`carboxylic acid by an akeohol
`is a reverse reaction,
`calalyaed by strong acids or Lewis acids. Carbonyl
`activation of a carboxylic group consists in transform-
`ing the hydroxyl
`into a better Icaving group. Acyl
`
`
`
`
`
`RIMFROST EXHIBIT 1177 Page 0014
`RIMFROST EXHIBIT 1177 Page 0014
`
`

`

`Zaz
`
`chlorides are the most frequently used derivatives.
`Activation of the alcohol consists in making it more
`active towards a nucleophilic attack of the carboxylate
`ion. Condensation of an alkaline carboxylate with an
`alkyl halide is favored by using dipolar aprotic solvents
`or phase-transfer conditions. In addition, diazome-
`thane is a wery active source of methyl groupe after
`deprotonation of the acid. Esterification of carboxylic
`acids can also be done by an enzymatic procedure in
`the presence of lipascs.
`Fatty acids are weak acids. Therefore, they may
`react with strong (hydroxides) or weak mineral bases.
`(carbonate, bicarbonate) and organic hascs (amines) to
`Produce metal salts and soaps. This property is used in
`the determination of acid valuc in fais, which measures
`the quantity of potassium hydroxide needed for
`neutralization of free acid in |g of fal Soape can be
`preacnt in small amounts in food lipids.
`Formation of nitrogenous derivatives from fatty
`acids, such as amides, is carried out to a high extent
`became ofthe surface-active propertics ofthe obtained
`products.
`Other reactions of the carboxyl group can produce
`fatty acid chlorides or anhydrides, sulfonic acids,
`peroxy acids, and aldchydes, among others.
`
`2. Reactions of the Aliphatic Chain
`Double bonds are much more reactive than aliphatic
`chains,
`therefore, most
`reactions occur cither in
`unsalurations or in the reactive allylic carbons. The
`reactions that take place in the double bonds are
`isomicrizations,
`including cit—trans isomerization and
`migrations of the double bonds, and addition reac-
`tions. Among addition reactions, hydrogenation & one
`of the most extensively used because it is an industrial
`Process to harden liquids oils for margarine or short-
`cning production. It is
`frequently accompanied by
`doubke-bond migration and ciz—trans isomerization to
`give a wide range of positional and configurational
`isomers. From a nutritional point of view, analysis of
`these isomers in foods is important since differenti
`studics attempted to show a correlation between trav
`fatty acid ingestion and an increase in blood choles-
`terol level (4-36) as well as a relationship between
`trans [aity acids and cardiovascular risks (37-39). As
`discussed above, hydrogenation ako occurs in the
`rumen of cows and sheep through the action of rumen
`bacteria.
`Other addition reactions arc: cposxidation, which
`Produces cpoxidized oils uaed as stabilincr—plasticizer
`compounds; hydroxylation,
`to add one of more
`
`famoru amd Hidalgo
`
`hydroxyl groupe to olefins to form akohols and
`glycols; halogenation, which produces halogenated
`derivatives with interest for analytical and synthetic
`purposcs and it & also the basis of the iodine valuc
`used for measuring total unsaturation, Dicls Alder
`reactions, with wide applications for the production of
`detergents, polyamides, hydrotropes, and foam regu-
`laters; and hydroformylation, which introduces carbon
`monoxide into the fatty acid molecule in the form
`of carbonyl (aldchyde, ketone, acid, ester, cic.) by
`creating a C—C bond. Details of these and other related
`reactions can be found in more specialiacd books
`(32,3340). As well as addition reactions, dowble bonds
`may be broken by ozonolysis, disruptive oxidation,
`Mmectathesis, or alkali
`fusion, all of them having
`analytical or industrial applications.
`Among the reactions kading to allylic derivatives,
`the most important is oxidation. Lipid oxidation is ome
`of the major causes of food spoilage. It is of great
`economic concem to the food industry becawec it leads
`to the development, in edible oils and fat-containing
`foods, of various off-fMavors and off-odors, decreases
`the nutrition