List of unsaturated fatty acids

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 
These fatty acids have one unsaturated bond.

 Crotonic acid 
Crotonic acid has 4 carbons. Their IUPAC name is C3H5 CO2H. Molecular weight 86.09, melting point 72–74 °C, boiling point 180–181 °C, specific gravity 1.027. CAS registry number 107-93-7.

149px|crotonic acid structure

 Myristoleic 
Myristoleic acid has 14 carbons. Their IUPAC name is C13H25CO2H. Molecular weight 226.36, melting point of −4.5 – −4 °C. CAS Registry Number 544-64-9.

360px|myristoleic acid structure

 Palmitoleic acid 
Palmitoleic acid has 16 carbons. Molecular weight 254.41, melting point 5 °C, specific gravity 0.894. CAS Registry Number 373-49-9.

396px|palmitoleic acid structure

 Sapienic acid 
Sapienic acid has 16 carbons. Molecular weight 254.41. CAS Registry Number 17004-51-2.

 Oleic acid 
Oleic acid has 18 carbons. Molecular weight 282.46, melting point 13.4 °C, specific gravity 0.891. CAS Registry Number 112-80-1.

437px|oleic acid structure

 Elaidic acid 
Elaidic acid has 18 carbons. Molecular weight 282.46, melting point 43–45 °C. CAS Registry Number 112-79-8.

531px|elaidic acid structure

 Vaccenic acid 
Vaccenic acid has 18 carbons. Molecular weight 282.46. CAS Registry Number 506-17-2.

454x454px|vaccenic acid structure

 Gadoleic acid 
Gadoleic acid has 20 carbons. Molecular weight 310.51. CAS Registry Number 29204-02-2.

456px|gadoleic acid structure

 Eicosenoic acid 
Eicosenoic acid has 20 carbons. Molecular weight 310.51. CAS Registry Number 5561-99-9.

483px|eicosenoic acid structure

 Erucic acid 
Erucic acid has 22 carbons. Molecular weight 338.57, melting point 33–35 °C. CAS Registry Number 112-86-7.

530px|erucic acid structure

 Nervonic acid 
Nervonic acid has 24 carbons. Molecular weight 366.62, melting point 42–43 °C. CAS Registry Number 506-37-6.

585px|nervonic acid structure

 Di-unsaturated fatty acid 
These fatty acids have two unsaturated bonds.

 Linoleic acid 
Linoleic acid has 18 carbons. Molecular weight 280.45, melting point −5 °C, specific gravity 0.902. CAS Registry Number 60-33-3.

540px|linoleic acid structure

 Eicosadienoic acid 
Eicosadienoic acid (eicosadienoic's) has 20 carbons. Molecular weight 308.50.

596px|eicosadienoic acid structure

 Docosadienoic acid 
Docosadienoic acid (docosadienoic's) has 22 carbons. Molecular weight 336.55. CAS Registry Number 7370-49-2.

647px|docosadienoic acid structure

 Tri-unsaturated fatty acids 
These fatty acids have three unsaturated bonds.

 Linolenic acid 
α-Linolenic acid (alpha-linolenic's) has 18 carbons. Molecular weight 278.43, melting point −11 °C, specific gravity 0.914. CAS Registry Number 463-40-1.

554px|α-linolenic acid structure

γ-Linolenic acid (gamma-linolenic's) has 18 carbons. CAS Registry Number 506-26-3.

551px|γ-linolenic acid structure

 Pinolenic acid 
Pinolenic acid (pinolenic's) has 18 carbons. Molecular weight 278.43. CAS Registry Number 16833-54-8.

547px|pinolenic acid structure

 Eleostearic acid 
α-Eleostearic acid (alpha-eleostearic's) has 18 carbons. Molecular weight 278.43.

547px|α-eleostearic acid structure

β-Eleostearic acid (beta-eleostearic's, beta-eleostearic acid) is an isomer of α-eleostearic acid.

536px|β-eleostearic acid structure
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. Molecular weight 306.48. CAS Registry Number 20590-32-3.

607px|Mead acid structure

 Dihomo-γ-linolenic acid 
Dihomo-γ-linolenic acid (dihomo-gamma-linolenic's, dihomo-gamma-linolenic acid, DGLA) has 20 carbons. Molecular weight 306.48. CAS Registry Number 1783-84-2.

607px|dihomo-γ-linolenic acid structure

 Eicosatrienoic acid 
Eicosatrienoic acid (eicosatrienoic's, eicosatrienoic acid) has 20 carbons. Molecular weight 306.48.

602px|eicosatrienoic acid structure

 Tetra-unsaturated fatty acids 
These fatty acids have four unsaturated bonds.

 Stearidonic acid 
Stearidonic acid (stearidonic's) has 18 carbons. Molecular weight 276.41. CAS Registry Number 20290-75-9.

563px|stearidonic acid structure

 Arachidonic acid 
Arachidonic acid (arachidonic's) has 20 carbons. Molecular weight 304.47, boiling point 169–171 °C. CAS Registry Number 506-32-1.

600px|arachidonic acid structure

 Eicosatetraenoic acid 
Eicosatetraenoic acid (eicosatetraenoic's) has 20 carbons. Molecular weight 304.47.

592px|eicosatetraenoic acid structure

 Adrenic acid 
Adrenic acid (adrenic'sd) has 22 carbons. Molecular weight 332.52. CAS Registry Number 28874-58-0.

646px|adrenic acid structure

 Penta-unsaturated fatty acids 
These fatty acids have five unsaturated bonds.

 Bosseopentaenoic acid 
Bosseopentaenoic acid (Boseopentaen's), has 20 carbons. Molecular weight 302.46 g·mol−1.Burgess, J.R.; De la Rosa, R.I.; Jacobs, R.S.; Butler, A (1991). "A new eicosapentaenoic acid formed from arachidonic acid in the coralline red algae Bossiella orbigniana". Lipids. 26 (2): 1057–1059. doi:10.1007/BF02544012

 Eicosapentaenoic acid 
Eicosapentaenoic acid (EPA) has 20 carbons. Molecular weight 302.45, melting point −54 – −53 °C, specific gravity 0.943. CAS Registry Number 10417-94-4.

616px|eicosapentaenoic acid structure

 Ozubondo acid 
Ozubondo acid (Ozubondo's, Osbond acid), has 22 carbons. Molecular weight 330.50. CAS Registry Number 25182-74-5

672px|Ozubondo acid structure

 Sardine acid 
Sardine acid (clupanodonic acid) has 22 carbons. Molecular weight 330.50.

657px|sardine acid structure

 Tetracosapentaenoic acid 
Tetracosapentaenoic acid has 24 carbons. Molecular weight 358.56.

720px|Tetracosapentaenoic acid structure

 Hexa-unsaturated fatty acids 
The following fatty acids have six unsaturated bonds.

 Cervonic acid 
Cervonic acid (or docosahexaenoic acid) has 22 carbons. Molecular weight 328.49, melting point −44 °C, specific gravity 0.950. CAS Registry Number 6217-54-5.

680px|Docosahexaenoic acid structure

 Herring acid 
Herring acid (Herring's, Nisinic acid) is a 6,9,12,15,18,21-hexa unsaturated fatty acid. It has 24 carbon atoms. Molecular weight 356.54.

726px|Nisinic acid structure

Related pages
List of saturated fatty acids
Carboxylic acid
Dicarboxylic acid

References


Unsaturated Fatty Acids