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Α-Linolenic acid
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==Dietary sources== {{See also|Vegetable oil#Composition of fats}} Seed oils are the richest sources of α-linolenic acid, notably those of hempseed, [[Salvia hispanica|chia]], [[Perilla oil|perilla]], [[flaxseed]] ([[linseed oil]]), [[rapeseed]] ([[canola]]), and [[soybean]]s. α-Linolenic acid is also obtained from the [[thylakoid|thylakoid membranes]] in the leaves of ''[[Pisum sativum]]'' (pea leaves).<ref>{{cite journal |author1=Chapman, David J. |author2=De-Felice, John |author3=Barber, James |journal=Plant Physiol |date=May 1983|volume=72 | issue=1|pages=225–228 |title=Growth temperature effects on thylakoid membrane lipid and protein content of pea chloroplasts 1 |pmid=16662966 |doi= 10.1104/pp.72.1.225 |pmc= 1066200}}</ref> Plant [[chloroplast]]s 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.<ref>YashRoy R.C. (1987) 13-C NMR studies of lipid fatty acyl chains of chloroplast membranes. ''Indian Journal of Biochemistry and Biophysics'' vol. 24(6), pp. 177–178.https://www.researchgate.net/publication/230822408_13-C_NMR_studies_of_lipid_fatty_acyl_chains_of_chloroplast_membranes?ev=prf_pub</ref> Some studies state that ALA remains stable during processing and cooking.<ref>{{cite journal|title=Processing and cooking effects on lipid content and stability of alpha-linolenic acid in spaghetti containing ground flaxseed. | pmid=11879055 | volume=50 | issue=6 | year=2002 | journal=J. Agric. Food Chem. | pages=1668–71 | doi=10.1021/jf011147s| last1=Manthey | first1=F. A. | last2=Lee | first2=R. E. | last3=Hall | first3=C. A. }}</ref> However, other studies state that ALA might not be suitable for baking as it will [[polymer]]ize with itself, a feature exploited in [[Drying oil|paint]] with transition metal catalysts. Some ALA may also oxidize at baking temperatures.<ref>{{cite web|url=http://serials.unibo.it/cgi-ser/start/it/spogli/df-s.tcl?prog_art=3832218&language=ITALIANO&view=articoli|title=OXIDATIVE STABILITY OF FLAXSEED LIPIDS DURING BAKING|access-date=30 December 2012|archive-date=16 October 2015|archive-url=https://web.archive.org/web/20151016210119/http://serials.unibo.it/cgi-ser/start/it/spogli/df-s.tcl?prog_art=3832218&language=ITALIANO&view=articoli|url-status=live}}</ref> ALA percentages in the table below refer to the oils extracted from each item. {| class="wikitable" style="border-collapse:collapse;" !|Common name||Alternate name||Linnaean name||% ALA<sup>†</sup>(of oil)||ref. |- |[[Chia seed|Chia]] ||chia sage||''Salvia hispanica''||64% ||<ref name=sofadb>{{Cite web |url=http://sofa.mri.bund.de/ |title=Seed Oil Fatty Acids – SOFA Database Retrieval |access-date=26 March 2018 |archive-date=9 November 2018 |archive-url=https://web.archive.org/web/20181109135217/http://sofa.mri.bund.de/ |url-status=live }}</ref> |- |[[Kiwifruit]] seeds||Chinese gooseberry||''Actinidia chinensis''||62%||<ref name=sofadb /> |- |[[Perilla]]||shiso||''Perilla frutescens''||58%||<ref name=sofadb /> |- |[[Flax]]||linseed||''Linum usitatissimum''||55%||<ref name=sofadb /> |- |[[Cowberry|Lingonberry]]||cowberry||''Vaccinium vitis-idaea''||49%||<ref name=sofadb /> |- |[[Camelina sativa|Camelina]]||camelina||''Camelina sativa''||37%||<ref name= Juodka >{{cite journal |vauthors=Juodka R, Nainiené R, Juškiené V, Juška R, Leikus R, Kadžiené G, Stankevičiené D |date=January 2022 |title=Camelina (''Camelina sativa'' (L.) Crantz) as Feedstuffs in Meat Type Poultry Diet: A Source of Protein and n-3 Fatty Acids |journal=Animals |volume=12 |issue=3 |at=Table 3 |doi=10.3390/ani12030295 |doi-access=free|pmid=35158619 |pmc=8833380 }}</ref> |- |[[Portulaca|Purslane]]||portulaca||''Portulaca oleracea''||35%||<ref name=sofadb /> |- |[[Cuckoo flower]]||mayflower||''Cardamine pratensis''||35%||<ref name= Bederska-Łojewska >{{cite journal |vauthors=Bederska-Łojewska D, Pieszka M, Marzec A, Rudzińska M, Grygier A, Siger A, Cieślik-Boczula K, Orczewska-Dudek S, Migdał W |date=December 2021 |title=Physicochemical Properties, Fatty Acid Composition, Volatile Compounds of Blueberries, Cranberries, Raspberries, and Cuckooflower Seeds Obtained Using Sonication Method |journal=Molecules |volume=26 |issue=24 |at=Table 2 |doi=10.3390/molecules26247446 |doi-access=free|pmid=34946523 |pmc=8704999 }}</ref> |- |[[Cranberry]]||American cranberry||''Vaccinium macrocarpon''||35%||{{r|Bederska-Łojewska}} |- | [[Sea buckthorn]] ||seaberry ||''Hippophae rhamnoides'' L.||32%||<ref name=Li>{{cite conference | first = Thomas S. C. | last = Li | title = Sea buckthorn: New crop opportunity | book-title = Perspectives on new crops and new uses | pages = 335–337 | publisher = [[ASHS Press]] | year = 1999 | location = Alexandria, VA | url = http://www.hort.purdue.edu/newcrop/proceedings1999/v4-335.html | access-date = 2006-10-28| archive-url= https://web.archive.org/web/20060922084707/http://www.hort.purdue.edu/newcrop/proceedings1999/v4-335.html| archive-date= 22 September 2006 | url-status= live}}</ref> |- |[[Raspberry]]||raspberry||''Rubus idaeus''||31%||{{r|Bederska-Łojewska}} |- |[[Blueberry]]||[[bilberry]]||''Vaccinium myrtillus'' L.||29%||{{r|Bederska-Łojewska}} |- |[[Hemp]]||cannabis||''Cannabis sativa''||20%||<ref name=sofadb /> |- |[[Walnut oil|Walnut]]||English walnut / Persian walnut||''Juglans regia''||10.4%||<ref>{{Cite web |url=http://www.umm.edu/altmed/articles/omega-3-000316.htm |title=Omega-3 fatty acids |publisher=University of Maryland Medical Center|archive-url=https://web.archive.org/web/20091227023806/http://www.umm.edu/altmed/articles/omega-3-000316.htm |archive-date=27 December 2009 }}</ref> |- |[[Rapeseed]]||canola||''Brassica napus''||10%||<ref name=Beare /> |- | [[Soybean oil|Soybean]] ||soya||''Glycine max''||8%||<ref name=Beare /> |- | colspan=3| | colspan=2|<small><sup>†</sup>average value</small> |}
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