α-Linolenic acid
[4] Plant chloroplasts consisting of more than 95 percent of photosynthetic thylakoid membranes are highly fluid due to the large abundance of ALA, evident as sharp resonances in high-resolution carbon-13 NMR spectra.[6] However, other studies state that ALA might not be suitable for baking as it will polymerize with itself, a feature exploited in paint with transition metal catalysts.[23] In 1887, linolenic acid was discovered and named by the Austrian chemist Karl Hazura of the Imperial Technical Institute at Vienna (although he did not separate its isomers).[24] α-Linolenic acid was first isolated in pure form in 1909 by Ernst Erdmann and F. Bedford of the University of Halle an der Saale, Germany,[25] and by Adolf Rollett of the Universität Berlin, Germany,[26] working independently, as cited in J. W. McCutcheon's synthesis in 1942,[27] and referred to in Green and Hilditch's 1930s survey.A Wittig reaction of the phosphonium salt of [(Z-Z)-nona-3,6-dien-1-yl]triphenylphosphonium bromide with methyl 9-oxononanoate, followed by saponification, completed the synthesis.
Linolenic acidPreferred IUPAC nameCAS NumberChEMBLChemSpiderDrugBankECHA InfoCardIUPHAR/BPSPubChemCompTox DashboardSMILESChemical formulaMolar massDensityMelting pointBoiling pointstandard stateessential fatty acidflaxseedwalnutsvegetable oilsstructurecarboxylic aciddouble bondspolyunsaturatedregioisomergamma-linolenic acidomega-6 fatty acidoleic acidlinoleic acidperillalinseed oilrapeseedcanolasoybeansthylakoid membranesPisum sativumchloroplastspolymerizeKiwifruitLingonberryCamelinaPurslaneCuckoo flowerCranberrySea buckthornRaspberryBlueberrybilberryWalnutSoybeandesaturasestearic acidstearidonic acideicosatetraenoic acideicosapentaenoic aciddocosapentaenoic acid6,9,12,15,18,21-tetracosahexaenoic aciddocosahexaenoic acidbecomes rancidOxidative instabilityhydrogenatesoybean oiltrans fatscardiovascular diseasetriglyceridestotal cholesterolhigh-density lipoproteinlow-density lipoproteinUniversity of Halle an der SaaleUniversität BerlinsaponificationCanola oilFlax seed oilγ-Linolenic acidDrying oilList of n−3 fatty acidsEssential nutrientWheat germ oilASHS PressEarly Human DevelopmentOrganic SynthesesBiochem. J.SynthesisLipidsfatty acidsSaturatedPropionicButyricValericCaproicEnanthicCaprylicPelargonicCapricUndecylicLauricTridecylicMyristicPentadecylicPalmiticMargaricStearicNonadecylicArachidicHeneicosylicBehenicTricosylicLignocericPentacosylicCeroticCarbocericMontanicNonacosylicMelissicHentriacontylicLacceroicPsyllicGeddicCeroplasticHexatriacontylicHeptatriacontanoicω−3 UnsaturatedStearidonicα-ParinaricEicosatetraenoic