I

3 9. o o ^ Ç. o « « 2 n ñ 5> i m S S S 6- s. n. a: S-s; O- a a CL

OQQQOOG

c7-Te!radecenoic acid (mynstoteic acid)

c9>Hexadecenoic acid I pa I rni (oleic acid)

HOOC~CW=W\AAA

c6-Octadecenotc acid (petroselinic acid)

HOOC"GHWV\=MAA

c9-Octadecenoic acid (oleic acid)

HOOC~CHWVVWW\

cl 1 -Octadecenoic acid (cis-vaccenic add)

HOOC_CVVWV\=AAM

c13-Docosaenic acid (eoictc acid) Figurm 6.2 Gs- and trans unsaturated fatty acids

[9-Hexadecenoic acid

H00C"CWWWW

t9-Octadecenoic acid (eiaidic acid)

HOOC_CWVWVW

111-Octadecenoic acid (trans-vaccenic acid)

H^~CWVV\AAAAA/

113-Docosaenoic acid (brassidic acid)

easier to refer to arachidonic aeid which unambiguously identifies cicosa-cis6,cisy, cis I2,cis 15-letraenoic aeid, than to use the systematic name.

If there are two or more double bonds in natural fatty acids, they usually recur at 3-carbon intervals. Two families of polyunsaturated fatty acids have particular metabolic importance and have to come from the diet. One family, the omega-3-fatty acids, comprises fatty acids with a double bond between the third and fourth carbon, counting from the acyl end and one or more double bonds at three carbon intervals. Because the counting for this nomenclature starts from the tail end a common notation uses the otnega symbol <ui. sometimes represented as w, or even V). because this is the last letter in the ("¡reek alphabet and traditionally has indicated the end. The other family, the omega-6-fatty acids, comprises fatty acids with double bonds between the sixth and seventh carbon, counting from the acyl end and one or more additional double bonds at three-carbon intervals from there.

Peroxidation by exposure to free radicals can modify unsaturated fatty acids and generate conjugated dienic double bonds adjacent to hydroperoxy or hydroxy groups that dramatically alter their chemical and metabolic properties (e.g. orientation in a membrane).

Tabla 6.3 Polyunsaturated fatty acids

Trivial iume Systematic name Carbons: double bonds

Omefp 6 PUFA Lin oleic acid Gamma-linalenic acid Di homo-gam ma-Itn ole nic acid Arachidonic acid Adrenic acid

Omega 3 PUFA

Alpha-linolenrc acid Steandonic acid Timnodonic acid Clupadomc acid

Other PUFA Mead actd

Conjugated Iinoletc actd (CLA) Rumenic acid (A CLA)

Octadeca-c9,cl2-dienoic acid Octadeca-c6,c9,c12-tnenoic acid Docom-cS.c 11 .cl 4'tnenoic acid Docosa-eS.cS.cl t,c14-tetraenoic acid Docosa-c7,cI0,cl3,cl6 tetraenoic acid, Ota Docosa-c4pc7.c'10,clJ,c16 peniaenoic acid

Hc*adeca-c4rc7,cl0,cl3-tctracnoic acid Octadcca-c9,cl2,clS-trienoic acid Octadeca-c6,c9,c12,c1S-tMraenoic acid Eicosa-c5,c8,c1 1,ct4,c17-pemaenoic acid, EPA Docosa-c7,c10,cI3,c16,c19-pentaenoic acid Docosa-c4,c7.c10,c 13,cl 6,cl 9-henaenoie, DHA

Eicosa-c3,c6,c9-trieno[c acid Cis9, trans 11 octadecadienoic acid

C18:2n6 C1S;3n6 C20:3n6 C20:4n6 C22:4n6 C22:5n6

C16:4n3 C18:3n3 C18:4n3 C20:5n3 C22:5n3 C22:6n3

C20:3n9

HOOC

HOOC

Hexadecaietraenoie acid 14.7,10.13-16 4>

HOOC

HOOC

HOOC

Siesndonrc acid {6.9.12.15-1841

Figure 6,3 Omega-3 polyunsaturated fatty acids

EtcoaapenlHeno*: acid

(5.8.11 14.17-20 5)

HOOC^X/

"V"

A-

-A-

-A-/

Docosapeniaonoic acid (4.7.10.13.16,19-22:6)

HOOC

Siesndonrc acid {6.9.12.15-1841

Figure 6,3 Omega-3 polyunsaturated fatty acids

Docosapeniaonoic acid (4.7.10.13.16,19-22:6)

HOOC

Qctadocaietiaeno*: acid 16,9.12.15-18 3)

Qctadocaietiaeno*: acid 16,9.12.15-18 3)

While ilie va.sl majority of fatty acids in foods have straight chains, there are a few hranched-chain fatty acids in certain foods Iso-fatty acids contain a methyl branch that extends from the second-to-last carbon; anteiso-fatty acids carry their methyl branch at the third-to-last carbon. The very short branehed-chain fatty acids are

HOOC

WWn HOOcW^Vn HOCcVW=V=\

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