α-Linolenic acid

α-Linolenic acid
Names
	Preferred IUPAC name (9Z,12Z,15Z)-Octadeca-9,12,15-trienoic acid
	Other names ALA; LNA; Linolenic acid; cis,cis,cis-9,12,15-Octadecatrienoic acid; (9Z,12Z,15Z)-9,12,15-Octadecatrienoic acid; Industrene 120
Identifiers
CAS Number	463-40-1 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:27432 ;
ChEMBL	ChEMBL8739 ;
ChemSpider	4444437 ;
DrugBank	DB00132 ;
ECHA InfoCard	100.006.669
IUPHAR/BPS	1049;
PubChem CID	5280934;
UNII	0RBV727H71 ;
CompTox Dashboard (EPA)	DTXSID7025506 ;
	InChI InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9- Key: DTOSIQBPPRVQHS-PDBXOOCHSA-N ; InChI=1/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9- Key: DTOSIQBPPRVQHS-PDBXOOCHBH;
	SMILES O=C(O)CCCCCCC\C=C/C\C=C/C\C=C/CC; CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)O;
Properties
Chemical formula	C18H30O2
Molar mass	278.436 g·mol−1
Density	0.9164 g/cm3
Melting point	−11 °C (12 °F; 262 K)
Boiling point	232 °C (450 °F; 505 K) at 17.0 mmHg
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

α-Linolenic acid, also known as alpha-linolenic acid (ALA) (from Greek alpha denoting "first" and linon meaning flax), is an n−3, or omega-3, essential fatty acid. ALA is found in many seeds and oils, including flaxseed, walnuts, chia, hemp, and many common vegetable oils.

In terms of its structure, it is named all-cis-9,12,15-octadecatrienoic acid.^[3] In physiological literature, it is listed by its lipid number, 18:3 (n−3). It is a carboxylic acid with an 18-carbon chain and three cis double bonds. The first double bond is located at the third carbon from the methyl end of the fatty acid chain, known as the n end. Thus, α-linolenic acid is a polyunsaturated n−3 (omega-3) fatty acid. It is a regioisomer of gamma-linolenic acid (GLA), an 18:3 (n−6) fatty acid (i.e., a polyunsaturated omega-6 fatty acid with three double bonds).

^ Loreau O, Maret A, Poullain D, Chardigny JM, Sébédio JL, Beaufrère B, Noël JP (2000). "Large-scale preparation of (9Z,12E)-[1-¹³C]-octadeca-9,12-dienoic acid, (9Z,12Z,15E)-[1-¹³C]-octadeca-9,12,15-trienoic acid and their 1-¹³C all-cis isomers". Chemistry and Physics of Lipids. 106 (1): 65–78. doi:10.1016/S0009-3084(00)00137-7. PMID 10878236.
^ ^a ^b Kim, K.-B.; Nam, Y. A.; Kim, H. S.; Hayes, A. W.; Lee, B.-M. α-Linolenic acid: Nutraceutical, pharmacological and toxicological evaluation. Food and Chemical Toxicology 2014, 70, 163–178.
^ Beare-Rogers (2001). "IUPAC Lexicon of Lipid Nutrition" (PDF). Archived (PDF) from the original on 12 February 2006. Retrieved 22 February 2006.

[1] Loreau O, Maret A, Poullain D, Chardigny JM, Sébédio JL, Beaufrère B, Noël JP (2000). "Large-scale preparation of (9Z,12E)-[1-¹³C]-octadeca-9,12-dienoic acid, (9Z,12Z,15E)-[1-¹³C]-octadeca-9,12,15-trienoic acid and their 1-¹³C all-cis isomers". Chemistry and Physics of Lipids. 106 (1): 65–78. doi:10.1016/S0009-3084(00)00137-7. PMID 10878236.

[Kim2014-2] Kim, K.-B.; Nam, Y. A.; Kim, H. S.; Hayes, A. W.; Lee, B.-M. α-Linolenic acid: Nutraceutical, pharmacological and toxicological evaluation. Food and Chemical Toxicology 2014, 70, 163–178.

[Beare-3] Beare-Rogers (2001). "IUPAC Lexicon of Lipid Nutrition" (PDF). Archived (PDF) from the original on 12 February 2006. Retrieved 22 February 2006.

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