ω−n Common name Lipid Numbers Δn Structural Formula Trans or Cis Naturally Occurring in ω−3 α-Linolenic acid C18:3 Δ9,12,15 CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7COOH cis flaxseeds, chia seeds, walnuts ω−3 Stearidonic acid C18:4 Δ6,9,12,15 CH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CH( CH2)4COOH cis seed oils of hemp, blackcurrant, corn gromwell ω−3 Eicosapentaenoic acid C20:5 Δ5,8,11,14,17 CH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2 CH=CH(CH2)3COOH cis cod liver, herring, mackerel, salmon, menhaden and sardine ω−3 Cervonic acid C22:6 Δ4,7,10,13,16,19 CH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2 CH=CHCH2CH=CH(CH2)2COOH cis maternal milk, fish oil ω−6 Linoleic acid C18:2 Δ9,12 CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH cis peanut oil,Oil, peanut, salad or cooking: search for peanut oil on chicken fat, olive oil ω−6 Linolelaidic acid C18:2 Δ9,12 CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH trans partially hydrogenated vegetable oils ω−6 γ-Linolenic acid C18:3 Δ6,9,12 CH3(CH2)4CH=CHCH2CH=CHCH2CH=CH(CH2)4COOH cis borage oil, black currant oil, evening primrose oil and safflower oil ω−6 Dihomo-γ-linolenic acid C20:3 Δ8,11,14 CH3(CH2)4CH=CHCH2CH=CHCH2CH=CH(CH2)6COOH cis only in trace amounts in animal productsHorrobin, D. F., 1990a. Gamma linolenic acid. Rev. Contemp. Pharmacother. 1, 1-45Huang, Y.-S. and Mills, D. E. (Eds.), 1996. Gamma-linolenic acid metabolism and its roles in nutrition and medicine. AOCS Press, Champaign, Illinois, 319 pp. ω−6 Arachidonic acid C20:4 Δ5,8,11,14 CH3(CH2)4CH=CHCH2CH=CHCH2CH=CHCH2 CH=CH(CH2)3COOH cis ω−6 Docosatetraenoic acid C22:4 Δ7,10,13,16 CH3(CH2)4CH=CHCH2CH=CHCH2CH=CHCH2 CH=CH(CH2)5COOH cis ω−7 Palmitoleic acid C16:1 Δ9 CH3(CH2)5CH=CH(CH2)7COOH cis macadamia nuts ω−7 Vaccenic acid C18:1 Δ11 CH3(CH2)5CH=CH(CH2)9COOH trans dairy products such as milk, butter, and yogurtNatural trans fats may be good for you. May 19, 2008 ω−7 Paullinic acid C20:1 Δ13 CH3(CH2)5CH=CH(CH2)11COOH cis guarana ω−9 Oleic acid C18:1 Δ9 CH3(CH2)7CH=CH(CH2)7COOH cis olive oil, pecan oil, canola oil ω−9 Elaidic acid C18:1 Δ9 CH3(CH2)7CH=CH(CH2)7COOH trans hydrogenated vegetable oil ω−9 Gondoic acid C20:1 Δ11 CH3(CH2)7CH=CH(CH2)9COOH cis jojoba oil (edible but non-caloric and non-digestible) ω−9 Erucic acid C22:1 Δ13 CH3(CH2)7CH=CH(CH2)11COOH cis wallflower seed, mustard oil ω−9 Nervonic acid C24:1 Δ15 CH3(CH2)7CH=CH(CH2)13COOH cis King salmon, flaxseed, sockeye salmon, sesame seed, macadamia nuts ω−9 Mead acid C20:3 Δ5,8,11 CH3(CH2)7CH=CHCH2CH=CHCH2CH=CH(CH2)3COOH cis cartilage

Fatty acid molecular species

Mono-unsaturated fatty acid The following fatty acids have one unsaturated bond.

Crotonic acid Crotonic acid has 4 carbons, is included in croton oil, and is a trans-2-mono-unsaturated fatty acid. C3H5 CO2H, IUPAC organization name (E)-but-2-enoic acid, trans-but-2-enoic acid, numerical representation 4:1, n-1, molecular weight 86.09, melting point 72–74 °C, boiling point 180–181 °C, specific gravity 1.027. CAS registry number 107–93–7.

Myristoleic Myristoleic acid has 14 carbons, is found in whale blubber, and is a cis-9-monounsaturated fatty acid. C13H25CO2H, IUPAC organization name (Z)-tetradec-9-enoic acid, numerical representation 14:1, n-5, molecular weight 226.36, melting point of −4.5 – −4 °C. CAS Registry Number 544–64–9.

Palmitoleic acid Palmitoleic acid has 16 carbons, is found in cod liver oil, sardine oil, and herring oil, and is a cis-9-monounsaturated fatty acid. C15H29CO2H, IUPAC organization name (Z)-hexadec-9-enoic acid, n-7, numerical representation of 16:1, molecular weight 254.41, melting point 5 °C, specific gravity 0.894. CAS Registry Number 373–49–9.

Sapienic acid Sapienic acid has 16 carbons, is found in the skin, and is a cis-6-mono-unsaturated fatty acid. C15H29CO2H, IUPAC organization name (Z)-6-Hexadecenoic acid, n-10, numerical expression 16:1, molecular weight 254.41. CAS Registry Number 17004–51–2.

Oleic acid Oleic acid has 18 carbons, is found in most animal fats and olive oil, and is a cis-9-monounsaturated fatty acid. C17H33CO2H, IUPAC organization name (Z)-octadec-9-enoic acid, numerical representation 18:1 (9), n-9, molecular weight 282.46, melting point 13.4 °C, specific gravity 0.891. CAS Registry Number 112–80–1.

Elaidic acid Elaidic acid has 18 carbons and is a trans-9-mono-unsaturated fatty acid. It is also a trans isomer of oleic acid. C17H33CO2H, IUPAC organization name (E)-octadec-9-enoic acid, numerical representation 18:1 (9), n-9, molecular weight 282.46, melting point 43–45 °C. CAS Registry Number 112–79–8.

Vaccenic acid Vaccenic acid has 18 carbons, is found in beef tallow, mutton, and butter, and is a trans-11-mono-unsaturated fatty acid. C17H33CO2H, IUPAC organization name (E)-octadec-11-enoic acid, numerical representation 18:1 (11) n-7, molecular weight 282.46. CAS Registry Number 506–17–2.

Gadoleic acid Gadoleic acid has 20 carbons, is found in cod liver oil and other marine animal oils, and is a cis-9-mono-unsaturated fatty acid. C19H37CO2H, IUPAC organization name (Z)-icos-9-enoic acid, numerical representation 20:1 (9), n-11, molecular weight 310.51. CAS Registry Number 29204–02–2.

Eicosenoic acid Eicosenoic acid has 20 carbons, is found in a wide variety of plant oils, and is a cis-11-mono-unsaturated fatty acid. C19H37CO2H, IUPAC organization name (Z)-icos-11-enoic acid, numerical representation 20:1 (11), n-9, molecular weight 310.51. CAS Registry Number 5561–99–9.

Erucic acid Erucic acid has 22 carbons, is found in rapeseed oil and mustard oil, and is a cis-13-monounsaturated is a fatty acid. C21H41CO2H, IUPAC organization name (Z)-docos-13-enoic acid, numerical representation 22:1, n-9, molecular weight 338.57, melting point 33–35 °C. CAS Registry Number 112–86–7.

Nervonic acid Nervonic acid has 24 carbons, is found in brain glycolipids (Nervon) and sphingomyelin, and is a cis-15-mono-unsaturated fatty acid. C23H45CO2H, IUPAC organization name (Z)-tetracos-15-enoic acid, numerical representation 24:1, n-9, molecular weight 366.62, melting point 42–43 °C. CAS Registry Number 506–37–6.

Di-unsaturated fatty acid The following fatty acids have two unsaturated bonds.

Linoleic acid Linoleic acid has 18 carbons, is contained in many vegetable oils, particularly semi-drying oils, and is a cis-9-cis-12-di-unsaturated fatty acid. C17H31CO2H, IUPAC organization name (9Z, 12Z)-octadeca-9,12-dienoic acid, numerical representation 18:2 (9,12), n-6, molecular weight 280.45, melting point −5 °C, specific gravity 0.902. CAS Registry Number 60–33–3. There are isomers of linoleic acid with double bonds separated by one single bond. They are named conjugated linoleic acids.

Eicosadienoic acid Eicosadienoic acid (eicosadienoic's) has 20 carbons and is a cis-11-cis-14-di-unsaturated fatty acid. C19H35CO2H, IUPAC organization name (11Z, 14Z)-icosa-11,14-dienoic acid, numerical representation 20:2 (11,14), n-6, molecular weight 308.50.

Docosadienoic acid Docosadienoic acid (docosadienoic's) has 22 carbons and is a cis-13-cis-16-di-unsaturated fatty acid. C21H39CO2H, IUPAC organization name (13Z, 16Z)-docosa-13,16-dienoic acid, numerical representation 22:2 (13,16), n-6, molecular weight 336.55. CAS Registry Number 7370–49–2.

Tri-unsaturated fatty acids The following fatty acids have three unsaturated bonds.

Linolenic acid α-Linolenic acid (alpha-linolenic's) has 18 carbons, is found in linseed oil and drying oil, and is a 9,12,15-tri-unsaturated fatty acid. C17H29CO2H, IUPAC organization name (9Z, 12Z, 15Z)-octadeca-9,12,15-trienoic acid, numerical representation 18:3 (9,12,15), n-3, molecular weight 278.43, melting point −11 °C, specific gravity 0.914. CAS Registry Number 463–40–1.

γ-Linolenic acid (gamma-linolenic's) has 18 carbons, is the structural isomer of α-linolenic acid. IUPAC organization name (6Z, 9Z, 12Z)-octadeca-6,9,12-trienoic acid, numerical representation 18:3 (6,9,12), n-6. CAS Registry Number 506–26–3.

Pinolenic acid Pinolenic acid (pinolenic's) has 18 carbons, is found in pine nuts, and is a 5,9,12-triunsaturated fatty acid. C17H29CO2H, IUPAC organization name (5Z, 9Z, 12Z)-octadeca-5,9,12-trienoic acid, numerical representation 18:3 (5,9,12), n-6, molecular weight 278.43. CAS Registry Number 16833–54–8.

Eleostearic acid α-Eleostearic acid (alpha-eleostearic's) has 18 carbons, is found in Kiri drying oil, and is a 9,11,13-triunsaturated fatty acid. C17H29CO2H, IUPAC organization name (9Z, 11E, 13E)-octadeca-9,11,13-trienoic acid, numerical representation 18:3 (9,11,13), n-5, molecular weight 278.43.

β-Eleostearic acid (beta-eleostearic's, beta-eleostearic acid) is a geometric isomer of α-eleostearic acid. IUPAC organization name (9E, 11E, 13E)-octadeca-9,11,13-trienoic acid, numerical representation 18:3 (9,11,13), n-5.

α- and β-Eleostearic acids are cis–trans isomers. Other cis–trans isomers of eleostearic acid are:

Catalpic acid (9E, 11E, 13Z) Punicic acid (9Z, 11E, 13Z).

Mead acid Mead acid (Mead's) has 20 carbons, is a 5,8,11-tri-unsaturated fatty acid. C19H33CO2H, IUPAC organization name (5Z, 8Z, 11Z)-icosa-5,8,11-trienoic acid, numerical representation 20:3 (5,8,11), n-9, molecular weight 306.48. CAS Registry Number 20590–32–3.

Dihomo-γ-linolenic acid Dihomo-γ-linolenic acid (dihomo-gamma-linolenic's, dihomo-gamma-linolenic acid, DGLA) has 20 carbons, and is an 8,11,14-tri-unsaturated fatty acid. C19H33CO2H, IUPAC organization name (8Z, 11Z, 14Z)-icosa-8,11,14-trienoic acid, numerical representation 20:3 (8,11,14), n-6, molecular weight 306.48. CAS Registry Number 1783–84–2.

Eicosatrienoic acid Eicosatrienoic acid (eicosatrienoic's, eicosatrienoic acid) has 20 carbons and is an 11,14,17- tri unsaturated fatty acid. C19H33CO2H, IUPAC organization name (11Z, 14Z, 17Z)-icosa-11,14,17-trienoic acid, numerical representation 20:3 (11,14,17), n-3, molecular weight 306.48.

Tetra-unsaturated fatty acids The following fatty acids have four unsaturated bonds.

Stearidonic acid Stearidonic acid (stearidonic's) has 18 carbons, is found in sardine oil and herring oil, and is a 6,9,12,15-tetraunsaturated fatty acid. C17H27CO2H, IUPAC organization name (6Z, 9Z, 12Z, 15Z)-octadeca-6,9,12,15-tetraenoic acid, numerical representation 18:4 (6,9,12,15), n-3, molecular weight 276.41. CAS Registry Number 20290–75–9.

Arachidonic acid Arachidonic acid (arachidonic's) has 20 carbons, is present in animal visceral fat (brain, liver, kidney, lung, spleen), and is a 5,8,11,14-tetra-unsaturated fatty acid. C19H31CO2H, IUPAC organization name (5Z, 8Z, 11Z, 14Z)-icosa-5,8,11,14-tetraenoic acid, numerical representation 20:4 (5,8,11,14), n-6, molecular weight 304.47, boiling point 169–171 °C. CAS Registry Number 506–32–1.

In signal transduction, arachidonic acid is produced through decomposition of the phospholipid cell membrane. This gives rise to the arachidonic acid cascade, a metabolic pathway that yields lipid mediator compounds such as prostaglandins, thromboxanes and leukotrienes. This pathway has attracted study for its key role in inflammatory diseases such as asthma.

Eicosatetraenoic acid Eicosatetraenoic acid (eicosatetraenoic's) has 20 carbons and is an 8,11,14,17-tetraunsaturated fatty acid. C19H31CO2H, IUPAC organization name (8Z, 11Z, 14Z, 17Z)-icosa-8,11,14,17-tetraenoic acid, numerical representation 20:4 (8,11,14,17), n-3, molecular weight 304.47.

Adrenic acid Adrenic acid (adrenic'sd) has 22 carbons and is a 7,10,13,16-tetra-unsaturated fatty acid. C21H35CO2H, IUPAC organization name (7Z, 10Z, 13Z, 16Z)-docosa-7,10,13,16-tetraenoic acid, numerical representation 22:4 (7,10,13,16), n-6, molecular weight 332.52. CAS Registry Number 28874–58–0.

Penta-unsaturated fatty acids The following fatty acids have five unsaturated bonds.

Bosseopentaenoic acid