Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:42:00 UTC
NP-MRD IDNP0000694
Secondary Accession NumbersNone
Natural Product Identification
Common NameAlpha-Linolenic acid
DescriptionAlpha-Linolenic acid (ALA) is a polyunsaturated fatty acid (PUFA). It is a member of the group of essential fatty acids called omega-3 fatty acids. Alpha-Linolenic acid, in particular, is not synthesized by mammals and therefore is an essential dietary requirement for all mammals. Certain nuts (English walnuts) and vegetable oils (canola, soybean, flaxseed/linseed, olive) are particularly rich in alpha-linolenic acid. Omega-3 fatty acids get their name based on the location of one of their first double bond. In all omega-3 fatty acids, the first double bond is located between the third and fourth carbon atom counting from the methyl end of the fatty acid (n-3). Although humans and other mammals can synthesize saturated and some monounsaturated fatty acids from carbon groups in carbohydrates and proteins, they lack the enzymes necessary to insert a cis double bond at the n-6 or the n-3 position of a fatty acid. Omega-3 fatty acids like alpha-linolenic acid are important structural components of cell membranes. When incorporated into phospholipids, they affect cell membrane properties such as fluidity, flexibility, permeability, and the activity of membrane-bound enzymes. Omega-3 fatty acids can modulate the expression of a number of genes, including those involved with fatty acid metabolism and inflammation. Alpha-Linolenic acid and other omega-3 fatty acids may regulate gene expression by interacting with specific transcription factors, including peroxisome proliferator-activated receptors (PPARs) and liver X receptors (LXRs). Alpha-Linolenic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism.
(9,12,15)-Linolenic acidChEBI
(9Z,12Z,15Z)-Octadecatrienoic acidChEBI
(Z,Z,Z)-9,12,15-Octadecatrienoic acidChEBI
9,12,15-Octadecatrienoic acidChEBI
9-cis,12-cis,15-cis-Octadecatrienoic acidChEBI
all-cis-9,12,15-Octadecatrienoic acidChEBI
cis,cis,cis-9,12,15-Octadecatrienoic acidChEBI
cis-Delta(9,12,15)-Octadecatrienoic acidChEBI
Linolenic acidChEBI
cis-Δ(9,12,15)-octadecatrienoic acidGenerator
a-Linolenic acidGenerator
Α-linolenic acidGenerator
alpha Linolenic acidHMDB
cis-9,12,15-Octadecatrienoic acidHMDB
Industrene 120HMDB
Chemical FormulaC18H30O2
Average Mass278.4296 Da
Monoisotopic Mass278.22458 Da
IUPAC Name(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
Traditional Nameα linolenic acid
CAS Registry Number463-40-1
InChI Identifier
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Abramis bramaFooDB
Acanthopanax gracilistylusKNApSAcK Database
Actinidia chinensisFooDB
Aegle marmelosPlant
Agaricus bisporusFooDB
Allium ampeloprasumFooDB
Allium ascalonicum
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosum
Allium hirtifoliumPlant
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosum
Aloe vera var.chinensisKNApSAcK Database
Aloysia triphylla
Alpinia oxyphyllaKNApSAcK Database
Amelanchier alnifolia
Anabaena flos-aquaeKNApSAcK Database
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anarhichas lupusFooDB
Anethum graveolensFooDB
Angelica keiskei
Annona cherimolaFooDB
Annona muricata
Annona reticulata
Annona squamosa
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulce
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgaris
Artocarpus altilisFooDB
Artocarpus heterophyllus
Asparagus officinalisFooDB
Astragalus mongholicusKNApSAcK Database
Attalea speciosa
Auricularia auricula-judae
Auricularia polytricha
Avena sativa L.FooDB
Averrhoa carambolaKNApSAcK Database
Azadirachta indicaKNApSAcK Database
Basella alba
Belone beloneFooDB
Benincasa hispida
Bertholletia excelsaFooDB
Beta vulgaris
Beta vulgaris ssp. ciclaFooDB
Borago officinalisFooDB
Bos taurusFooDB
Brassica alboglabra
Brassica juncea
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridis
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensis
Brassica rapa var. rapaFooDB
Brassica ruvo
Brosimum alicastrum
Bupleurum chinenseKNApSAcK Database
Byrsonima crassifolia
Cajanus cajanFooDB
Calophyllum calabaKNApSAcK Database
Calophyllum inophyllumKNApSAcK Database
Canarium ovatum
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capsicum annuumFooDB
Capsicum annuum L.
Capsicum annuum var. annuumFooDB
Capsicum chinense
Capsicum pubescens
Carica papaya L.FooDB
Carissa macrocarpa
Carthamus tinctoriusKNApSAcK Database
Carum carviFooDB
Carya illinoinensisFooDB
Castanea crenata
Castanea mollissima
Castanea sativa
Celosia cristadaKNApSAcK Database
Ceratonia siliquaFooDB
Chamaemelum nobileKNApSAcK Database
Chamerion angustifolium
Chenopodium album
Chenopodium quinoa
Chlorella vulgarisKNApSAcK Database
Chrysanthemum coronarium
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
Cinnamomum aromaticum
Cinnamomum verum
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifolia
Citrus limonFooDB
Citrus maxima
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Clitoria ternataKNApSAcK Database
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
Corylus avellana
Crataegus pinnatifidaKNApSAcK Database
Crateva religiosa
Crocus sativusFooDB
Croton tigliumKNApSAcK Database
Cucumis meloFooDB
Cucumis metuliferus
Cucumis sativus L.FooDB
Cucurbita maximaFooDB
Cucurbita moschata
Cullen corylifoliumPlant
Cuminum cyminum
Curcuma longaPlant
Cydonia oblongaFooDB
Cymbopogon citratus
Cynara cardunculus
Cynara scolymusFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dimocarpus longan
Dioscorea pentaphyllaFooDB
Diospyros kaki
Diospyros virginiana
Drymaria cordataKNApSAcK Database
Durio zibethinus
Dysphania ambrosioides
Echium auberianumKNApSAcK Database
Echium boissieriKNApSAcK Database
Echium gentianoidesKNApSAcK Database
Echium giganteumKNApSAcK Database
Echium lusitanicumKNApSAcK Database
Echium pitardiiKNApSAcK Database
Echium plantagineumKNApSAcK Database
Echium sabulicolaKNApSAcK Database
Echium strictumKNApSAcK Database
Echium vulgareKNApSAcK Database
Eleocharis dulcis
Elettaria cardamomumFooDB
Empetrum nigrum
Epimedium brevicornumKNApSAcK Database
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Esox luciusFooDB
Eugenia javanica
Eugenia uniflora
Eutrema japonicum
Fagopyrum esculentumFooDB
Fagopyrum tataricum
Feijoa sellowiana
Ficus caricaFooDB
Flammulina velutipes
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Gallus gallusFooDB
Garcinia mangostana
Gaylussacia baccata
Ginkgo bilobaFooDB
Glycine maxKNApSAcK Database
Grifola frondosa
Hedysarum alpinum
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffa
Hippoglossus hippoglossusFooDB
Hippophae rhamnoidesKNApSAcK Database
Hoplostethus atlanticusFooDB
Hordeum vulgareFooDB
Hyssopus officinalis L.
Ictalurus punctatusFooDB
Illicium verum
Ipomoea aquatica
Ipomoea batatasFooDB
Jasminum auriculatumKNApSAcK Database
Juglans ailanthifolia
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria siceraria
Lagopus mutaFooDB
Lathyrus sativus
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodes
Lepidium meyenii MacaKNApSAcK Database
Lepidium sativumFooDB
Lepus timidusFooDB
Levisticum officinale
Limanda limandaFooDB
Linum usitatissimumKNApSAcK Database
Litchi chinensisFooDB
Lota lotaFooDB
Luffa aegyptiaca
Lupinus albusFooDB
Lycium chinenseKNApSAcK Database
Macadamia tetraphylla
Malpighia emarginata
Malus pumilaFooDB
Mammea americana
Mangifera indicaKNApSAcK Database
Manihot esculentaFooDB
Manilkara zapota
Maranta arundinacea
Matricaria recutita
Matteuccia struthiopteris
Medicago sativaFooDB
Melanogrammus aeglefinusFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.
Mentha aquatica
Mentha arvensis
Mentha spicataFooDB
Mentha x piperitaFooDB
Merlangius merlangusFooDB
Mespilus germanica
Metroxylon sagu
Micromesistius poutassouFooDB
Microstomus kittFooDB
Molva molvaFooDB
Momordica charantiaFooDB
Morella rubra
Moringa oleifera
Morus nigra
Mucuna puriensPlant
Musa acuminata
Musa x paradisiacaFooDB
Myristica fragransFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceum
Nephrops norvegicusFooDB
Nicotiana tabacumKNApSAcK Database
Nigella sativa LKNApSAcK Database
Nuphar luteaFooDB
Nymphaea albaKNApSAcK Database
Ocimum basilicumFooDB
Octopus vulgarisFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
Oncorhynchus gorbuschaFooDB
Oncorhynchus kisutchFooDB
Oncorhynchus mykissFooDB
Oncorhynchus nerkaFooDB
Ophiocordyceps sinensisFungi
Opuntia cochenillifera
Opuntia macrorhiza
Origanum majoranaFooDB
Origanum onites
Origanum vulgareFooDB
Origanum X majoricum
Oryza rufipogon
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginseng
Pangium edule
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentum
Perideridia oregana
Perilla frutescens var.argutaKNApSAcK Database
Persea americanaFooDB
Petasites japonicus
Petroselinum crispumFooDB
Phaseolus coccineus
Phaseolus lunatus
Phaseolus vulgarisFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpa
Phyllostachys edulisFooDB
Physalis philadelphica var. immaculata
Phytolacca americana
Pimenta dioica
Pimpinella anisum
Pinus edulisFooDB
Pinus sibiricaKNApSAcK Database
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Pleurotus ostreatusFooDB
Polygonum alpinum
Portulaca oleraceaFooDB
Potentilla asiaticaKNApSAcK Database
Potentilla desertorumKNApSAcK Database
Potentilla orientalisKNApSAcK Database
Poterium polygamum-
Pouteria sapota
Prunus armeniacaKNApSAcK Database
Prunus avium
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persica
Prunus tomentosa
Prunus virginiana
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Psoralea corylifoliaKNApSAcK Database
Punica granatumKNApSAcK Database
Pyrus communisFooDB
Pyrus pyrifolia
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativus
Reinhardtius hippoglossoidesFooDB
Rheum rhabarbarumFooDB
Ribes aureum
Ribes glandulosum
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
Rubus arcticus
Rubus chamaemorus
Rubus idaeusFooDB
Rubus occidentalis
Rubus spectabilis
Rumex acetosaFooDB
Rumex articus
Saccharina japonicaFooDB
Sagittaria latifolia
Salix pulchra
Salmo salarFooDB
Salvelinus namaycushFooDB
Salvia elegans
Salvia hispanica
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Sander luciopercaFooDB
Satureja hortensis L.FooDB
Satureja montana
Scophthalmus maximusFooDB
Scorzonera hispanicaFooDB
Scurrula atropurpureaKNApSAcK Database
Scurrura atropurpurea-
Sebastes alutusFooDB
Sebastes viviparusFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosa
Silybum marianumKNApSAcK Database
Sinapis albaFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiforme
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoense
Solanum tuberosumKNApSAcK Database
Sorbus aucuparia
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Squalus acanthiasFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticum
Syzygium cumini
Syzygium jambos
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
Theobroma cacaoFooDB
Thymus pulegioides
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia cordata Mill.KNApSAcK Database
Tilia L.FooDB
Tragopogon porrifolius
Trichosanthes kirilowiiKNApSAcK Database
Trichosanthes rosthorniiKNApSAcK Database
Trigonella foenum-graecumFooDB
Trisopterus esmarkiiFooDB
Triticum aestivumKNApSAcK Database
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Typha angustifolia
Typha domingensis P.KNApSAcK Database
Vaccinium angustifolium
Vaccinium angustifolium X Vaccinium corymbosum
Vaccinium arboreum
Vaccinium corymbosum
Vaccinium deliciosum
Vaccinium elliottii
Vaccinium macrocarpon
Vaccinium myrtilloides
Vaccinium myrtillusFooDB
Vaccinium ovalifolium
Vaccinium ovatum
Vaccinium oxycoccos
Vaccinium parvifolium
Vaccinium reticulatum
Vaccinium stamineum
Vaccinium uliginosum
Vaccinium vitis-idaeaFooDB
Valerianella locusta
Verbena officinalis
Viburnum edule
Vicia fabaKNApSAcK Database
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellata
Vigna unguiculata
Vigna unguiculata ssp. cylindrica
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
Vitellaria paradoxaFooDB
Vitis aestivalis
Vitis labrusca
Vitis rotundifolia
Vitis vinifera L.FooDB
Withania somniferaPlant
Xanthosoma sagittifolium
Zea mays L.FooDB
Zingiber officinaleFooDB
Zizania aquatica
Ziziphus zizyphus
Species Where Detected
Species NameSourceReference
Cordyceps sinensisKNApSAcK Database
Homo sapiens (Serum)KNApSAcK Database
Psalliota bisporaKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentLineolic acids and derivatives
Alternative Parents
  • Octadecanoid
  • Long-chain fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
Experimental Properties
Melting Point-16.5 °CNot Available
Boiling Point230.00 to 231.00 °C. @ 1.00 mm HgThe Good Scents Company Information System
Water Solubility0.12 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.46Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.
Predicted Properties
Water Solubility0.00027 g/LALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity89.64 m³·mol⁻¹ChemAxon
Polarizability34.98 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
DrugBank IDDB00132
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031277
KNApSAcK IDC00007247
Chemspider ID4444437
KEGG Compound IDC06427
BiGG ID48237
Wikipedia LinkAlpha-Linolenic_acid
PubChem Compound5280934
PDB IDNot Available
ChEBI ID27432
Good Scents IDrw1045911
General References
  1. Richieri GV, Ogata RT, Kleinfeld AM: Equilibrium constants for the binding of fatty acids with fatty acid-binding proteins from adipocyte, intestine, heart, and liver measured with the fluorescent probe ADIFAB. J Biol Chem. 1994 Sep 30;269(39):23918-30. [PubMed:7929039 ]
  2. Bajaj M, Suraamornkul S, Romanelli A, Cline GW, Mandarino LJ, Shulman GI, DeFronzo RA: Effect of a sustained reduction in plasma free fatty acid concentration on intramuscular long-chain fatty Acyl-CoAs and insulin action in type 2 diabetic patients. Diabetes. 2005 Nov;54(11):3148-53. [PubMed:16249438 ]
  3. Christensen JH, Fabrin K, Borup K, Barber N, Poulsen J: Prostate tissue and leukocyte levels of n-3 polyunsaturated fatty acids in men with benign prostate hyperplasia or prostate cancer. BJU Int. 2006 Feb;97(2):270-3. [PubMed:16430627 ]
  4. Attar-Bashi NM, Frauman AG, Sinclair AJ: Alpha-linolenic acid and the risk of prostate cancer. What is the evidence? J Urol. 2004 Apr;171(4):1402-7. [PubMed:15017185 ]
  5. Rastogi SK, Singh J: Effect of chemical penetration enhancer and iontophoresis on the in vitro percutaneous absorption enhancement of insulin through porcine epidermis. Pharm Dev Technol. 2005;10(1):97-104. [PubMed:15776817 ]
  6. Allman MA, Pena MM, Pang D: Supplementation with flaxseed oil versus sunflowerseed oil in healthy young men consuming a low fat diet: effects on platelet composition and function. Eur J Clin Nutr. 1995 Mar;49(3):169-78. [PubMed:7774533 ]
  7. Fokkema MR, Brouwer DA, Hasperhoven MB, Martini IA, Muskiet FA: Short-term supplementation of low-dose gamma-linolenic acid (GLA), alpha-linolenic acid (ALA), or GLA plus ALA does not augment LCP omega 3 status of Dutch vegans to an appreciable extent. Prostaglandins Leukot Essent Fatty Acids. 2000 Nov;63(5):287-92. [PubMed:11090255 ]
  8. Becker CC, Lund P, Holmer G, Jensen H, Sandstrom B: Effects of butter oil blends with increased concentrations of stearic, oleic and linolenic acid on blood lipids in young adults. Eur J Clin Nutr. 1999 Jul;53(7):535-41. [PubMed:10452408 ]
  9. Jones DB, Scaretto L, Carter R, Mann JI: Glucose, insulin and platelet fatty acids following myocardial infarction: an association with infarct size. Diabete Metab. 1987 Jul-Aug;13(4):463-6. [PubMed:3315767 ]
  10. Crastes de Paulet A, Babin F, Billeaud C, Bougle D, Sarda P, Mendy F: [Biological effects on premature neonates of a milk formula enriched with alpha-linolenic acid: a multicenter study]. Bull Acad Natl Med. 1994 Feb;178(2):267-73; discussion 273-8. [PubMed:7913655 ]
  11. Li D, Sinclair A, Wilson A, Nakkote S, Kelly F, Abedin L, Mann N, Turner A: Effect of dietary alpha-linolenic acid on thrombotic risk factors in vegetarian men. Am J Clin Nutr. 1999 May;69(5):872-82. [PubMed:10232625 ]
  12. Bhatia KS, Singh J: Effect of linolenic acid/ethanol or limonene/ethanol and iontophoresis on the in vitro percutaneous absorption of LHRH and ultrastructure of human epidermis. Int J Pharm. 1999 Apr 15;180(2):235-50. [PubMed:10370194 ]
  13. Baylin A, Kabagambe EK, Ascherio A, Spiegelman D, Campos H: Adipose tissue alpha-linolenic acid and nonfatal acute myocardial infarction in Costa Rica. Circulation. 2003 Apr 1;107(12):1586-91. Epub 2003 Mar 10. [PubMed:12668490 ]
  14. Williard DE, Nwankwo JO, Kaduce TL, Harmon SD, Irons M, Moser HW, Raymond GV, Spector AA: Identification of a fatty acid delta6-desaturase deficiency in human skin fibroblasts. J Lipid Res. 2001 Apr;42(4):501-8. [PubMed:11290821 ]
  15. Campbell FM, Gordon MJ, Dutta-Roy AK: Preferential uptake of long chain polyunsaturated fatty acids by isolated human placental membranes. Mol Cell Biochem. 1996 Feb 9;155(1):77-83. [PubMed:8717442 ]
  16. Cunnane SC, Hamadeh MJ, Liede AC, Thompson LU, Wolever TM, Jenkins DJ: Nutritional attributes of traditional flaxseed in healthy young adults. Am J Clin Nutr. 1995 Jan;61(1):62-8. [PubMed:7825540 ]
  17. Connor WE: Importance of n-3 fatty acids in health and disease. Am J Clin Nutr. 2000 Jan;71(1 Suppl):171S-5S. [PubMed:10617967 ]
  18. Lauritzen I, Blondeau N, Heurteaux C, Widmann C, Romey G, Lazdunski M: Polyunsaturated fatty acids are potent neuroprotectors. EMBO J. 2000 Apr 17;19(8):1784-93. [PubMed:10775263 ]
  19. Cho E, Hung S, Willett WC, Spiegelman D, Rimm EB, Seddon JM, Colditz GA, Hankinson SE: Prospective study of dietary fat and the risk of age-related macular degeneration. Am J Clin Nutr. 2001 Feb;73(2):209-18. [PubMed:11157315 ]
  20. Kris-Etherton PM, Harris WS, Appel LJ: Fish consumption, fish oil, omega-3 fatty acids, and cardiovascular disease. Circulation. 2002 Nov 19;106(21):2747-57. [PubMed:12438303 ]
  21. Brouwer IA, Katan MB, Zock PL: Dietary alpha-linolenic acid is associated with reduced risk of fatal coronary heart disease, but increased prostate cancer risk: a meta-analysis. J Nutr. 2004 Apr;134(4):919-22. [PubMed:15051847 ]