Eicosapentaenoic acid (CED0001577)

Record Information
Version1.0
Creation Date2016-05-22 04:30:13 UTC
Update Date2026-05-14 16:24:22 UTC
Accession NumberCHEM017629
Identification
Common NameEicosapentaenoic acid
ClassSmall Molecule
Description
Eicosapentaenoic acid (C20H30O2) is a compound with an average molecular weight of 302.45 g/mol. Eicosapentaenoic acid belongs to the fatty acids and conjugates, a subclass of fatty acyls within the organic compounds. Industrially, it is used as a softener and conditioner. The compound is found in or released from 21 recorded sources. These include electrical and electronic equipment such as antennas, amplifiers, magnets, emergency protective devices, and cores yokes or armatures, among four others. Within the food, food processing and cookware category, it is associated with food contact materials, the preparation of malt, vinegar, wine or sparkling wine, and molasses and the treatment of molasses, among three others. In household cleaning and consumer products, it is found in tobacco product cases, other smoking requisites, and non-electric simulated smoking devices. Additionally, it is found in building and construction materials specifically relating to fencing. Recorded exposure routes for the compound include oral, inhalation, and touch. Eicosapentaenoic acid interacts with 12 recorded protein targets. It acts as an activator, agonist, or agonist for certain proteins and serves as a regulator, inducer, inhibitor, or substrate for Prostaglandin G/H synthase 1 (PTGS1), Prostaglandin G/H synthase 2 (PTGS2), Free fatty acid receptor 1 (FFAR1), and Acyl-CoA (8-3)-desaturase (FADS1), along with eight other proteins.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoic acidChEBI
(5Z,8Z,11Z,14Z,17Z)-EicosapentaenoateChEBI
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic acidChEBI
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acidChEBI
(all-Z)-5,8,11,14,17-Eicosapentaenoic acidChEBI
5,8,11,14,17-EICOSAPENTAENOIC ACIDChEBI
5,8,11,14,17-Icosapentaenoic acidChEBI
all-cis-5,8,11,14,17-Eicosapentaenoic acidChEBI
all-cis-Icosa-5,8,11,14,17-pentaenoic acidChEBI
cis, cis, cis, cis, cis-Eicosa-5,8,11,14,17-pentaenoic acidChEBI
cis-5,8,11,14,17-Eicosapentaenoic acidChEBI
cis-5,8,11,14,17-EPAChEBI
cis-Delta(5,8,11,14,17)-Eicosapentaenoic acidChEBI
EPAChEBI
IcosapentChEBI
Icosapentaenoic acidChEBI
IcosapentoChEBI
IcosapentumChEBI
Timnodonic acidChEBI
(5Z,8Z,11Z,14Z,17Z)-IcosapentaenoateKegg
5Z,8Z,11Z,14Z,17Z-Eicosapentaenoic acidKegg
(5Z,8Z,11Z,14Z,17Z)-Icosa-5,8,11,14,17-pentaenoic acidKegg
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-EicosapentaenoateGenerator
(all-Z)-5,8,11,14,17-EicosapentaenoateGenerator
5,8,11,14,17-EICOSAPENTAENOateGenerator
5,8,11,14,17-IcosapentaenoateGenerator
all-cis-5,8,11,14,17-EicosapentaenoateGenerator
all-cis-Icosa-5,8,11,14,17-pentaenoateGenerator
cis, cis, cis, cis, cis-Eicosa-5,8,11,14,17-pentaenoateGenerator
cis-5,8,11,14,17-EicosapentaenoateGenerator
cis-delta(5,8,11,14,17)-EicosapentaenoateGenerator
cis-Δ(5,8,11,14,17)-eicosapentaenoateGenerator
cis-Δ(5,8,11,14,17)-eicosapentaenoic acidGenerator
IcosapentaenoateGenerator
TimnodonateGenerator
5Z,8Z,11Z,14Z,17Z-EicosapentaenoateGenerator
(5Z,8Z,11Z,14Z,17Z)-Icosa-5,8,11,14,17-pentaenoateGenerator
EicosapentaenoateGenerator
Omega-3-eicosapentaenoic acidHMDB
Acid, eicosapentanoicHMDB
Eicosapentanoic acidHMDB
Omega 3 eicosapentaenoic acidHMDB
all-cis-IcosapentaenoateHMDB
all-cis-Icosapentaenoic acidHMDB
(5Z,8Z,11Z,14Z,17Z)-Eicosa-5,8,11,14,17-pentaenoic acidHMDB
(all-Z)-delta5,8,11,14,17-Eicosapentaenoic acidHMDB
(all-Z)-Δ5,8,11,14,17-eicosapentaenoic acidHMDB
(all-cis)-5,8,11,14,17-Eicosapentaenoic acidHMDB
FA(20:5(5Z,8Z,11Z,14Z,17Z))HMDB
FA(20:5n3)HMDB
Eicosapentaenoic acidHMDB
Chemical FormulaC20H30O2
Average Molecular Mass302.451 g/mol
Monoisotopic Mass302.225 g/mol
CAS Registry Number10417-94-4
IUPAC Name(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
Traditional Nameeicosapentaenoic acid
SMILESCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI IdentifierInChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
InChI KeyJAZBEHYOTPTENJ-JLNKQSITSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00029 g/LALOGPS
logP6.53ALOGPS
logP6.23ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity101.07 m³·mol⁻¹ChemAxon
Polarizability35.93 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-004l-9700000000-09ea61ed836b88205028Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-004l-9700000000-09ea61ed836b88205028Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-004l-5490000000-ee15446245c5d0190ca2Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0adr-9462000000-6310373b498d395ee4b1Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0029000000-02c67e3601df249d2476Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0009000000-1f183f43649d7b5d2f92Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-2987000000-6239462e49ad0240cfd9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0009000000-028a784c6c5a01da151cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000x-9600000000-177a8f3f229d3ffe1c4fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0039000000-41dbbfbea0e69ff3303dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-2988000000-6239462e49ad0240cfd9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udr-1196000000-2fd0631ba34b61c02823Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-5891000000-6b514ce76e6321b59f49Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052f-8950000000-5f7ac71eb4fd77059c96Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0029000000-63f4108595227b77b5f0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zfr-2079000000-c196324eb61e1a26da90Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9230000000-844643f720715a477b35Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0019000000-da419ae96bb8b07031deNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ue9-2179000000-483c2cd6dc1d5799c3e4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0596-9530000000-b5f6ca6a7368abde8826Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f79-3985000000-f0a1f1db5a552a314689Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001l-5910000000-a82843e1aa65987b4a17Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00l6-9600000000-da4dd030385c445969bcNot AvailableView Spectrum
MSMS Spectrumsplash10-05ox-9400000000-567226e93d65502352cdNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, H2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, H2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
5165.0Log mg/kg[2900:9200]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
494Food contact materialsFood, food processing & cookwareNot Available
496FencingBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
513Cores Yokes Or ArmaturesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
546Molasses And Treatment Of MolassesFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
577Watch ChainsHousehold itemsNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
597ChemosterilantsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
634BucklesTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
Pathways
4 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Peroxisome proliferator-activated receptor gamma structureClick to view 3D structurePeroxisome proliferator-activated receptor gammaP37231HumansPredicted (SEA)0.233548
Peroxisome proliferator-activated receptor alpha structureClick to view 3D structurePeroxisome proliferator-activated receptor alphaQ07869HumansPredicted (SEA)0.311397
Peroxisome proliferator-activated receptor delta structureClick to view 3D structurePeroxisome proliferator-activated receptor deltaQ03181HumansPredicted (SEA)0.311397
Click to view 3D structureOxoeicosanoid receptor 1Q8TDS5HumansPredicted (SEA)0.0778492
Free fatty acid receptor 4 structureClick to view 3D structureFree fatty acid receptor 4Q5NUL3HumansPredicted (SEA)0.700643
Click to view 3D structureTransient receptor potential cation channel subfamily V member 2Q9WUD2Rattus norvegicusPredicted (SEA)2.33548
Fatty acid-binding protein, adipocyte structureClick to view 3D structureFatty acid-binding protein, adipocyteP15090HumansPredicted (SEA)0.389246
Click to view 3D structureSeed linoleate 9S-lipoxygenaseP24095Glycine maxPredicted (SEA)0.0778492
Click to view 3D structureFatty-acid amide hydrolase 1O00519HumansPredicted (SEA)7.47353
Free fatty acid receptor 1 structureClick to view 3D structureFree fatty acid receptor 1O14842HumansPredicted (SEA)3.42537
Tyrosine-protein phosphatase non-receptor type 1 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 1P18031HumansPredicted (SEA)6.77288
Click to view 3D structureProstaglandin G/H synthase 2P79208Ovis ariesPredicted (SEA)0.233548
Click to view 3D structureCannabinoid receptor 1P20272Rattus norvegicusPredicted (SEA)10.3539
Click to view 3D structureEsteraseA3QR02Chilo suppressalisPredicted (SEA)0.544945
Retinoic acid receptor RXR-alpha structureClick to view 3D structureRetinoic acid receptor RXR-alphaP19793HumansPredicted (SEA)7.00643
Cannabinoid receptor 2 structureClick to view 3D structureCannabinoid receptor 2P34972HumansPredicted (SEA)13.2344
Cannabinoid receptor 1 structureClick to view 3D structureCannabinoid receptor 1P21554HumansPredicted (SEA)16.0369
Click to view 3D structureCannabinoid receptor 2P47936Mus musculusPredicted (SEA)6.77288
Click to view 3D structureFatty-acid amide hydrolase 1P97612Rattus norvegicusPredicted (SEA)9.809
Click to view 3D structureCannabinoid receptor 2Q9QZN9Rattus norvegicusPredicted (SEA)2.49118
Transient receptor potential cation channel subfamily V member 1 structureClick to view 3D structureTransient receptor potential cation channel subfamily V member 1Q8NER1HumansPredicted (SEA)12.6894
Click to view 3D structureSodium- and chloride-dependent GABA transporter 2P31646Rattus norvegicusPredicted (SEA)0.389246
Click to view 3D structureCannabinoid receptor 1P47746Mus musculusPredicted (SEA)6.85073
Click to view 3D structureTransient receptor potential cation channel subfamily V member 1O35433Rattus norvegicusPredicted (SEA)4.28171
Click to view 3D structureHistone deacetylase 11Q96DB2HumansPredicted (SEA)57.2192
Concentrations
Not Available
External Links
DrugBank IDDB00159
HMDB IDHMDB0001999
FooDB IDFDB030126
Phenol Explorer IDNot Available
KNApSAcK IDC00001215
BiGG ID2218016
BioCyc IDEICOSAPENTAENOATE
METLIN ID6423
PDB IDNot Available
Wikipedia LinkEicosapentaenoic acid
Chemspider ID393682
ChEBI ID28364
PubChem Compound ID446284
Kegg Compound IDC06428
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.
2. Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158.
3. Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987.
4. M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189
5. M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021
6. Sandri, Jacqueline; Viala, Jacques. Syntheses of all-(Z)-5,8,11,14,17-Eicosapentaenoic Acid and all-(Z)-4,7,10,13,16,19-Docosahexaenoic Acid from (Z)-1,1,6,6-tetraisopropoxy-3-hexene. Journal of Organic Chemistry (1995), 60(20), 6627-30.
7. Hafstrom I, Ringertz B, Gyllenhammar H, Palmblad J, Harms-Ringdahl M: Effects of fasting on disease activity, neutrophil function, fatty acid composition, and leukotriene biosynthesis in patients with rheumatoid arthritis. Arthritis Rheum. 1988 May;31(5):585-92.
8. Woodman RJ, Mori TA, Burke V, Puddey IB, Barden A, Watts GF, Beilin LJ: Effects of purified eicosapentaenoic acid and docosahexaenoic acid on platelet, fibrinolytic and vascular function in hypertensive type 2 diabetic patients. Atherosclerosis. 2003 Jan;166(1):85-93.
9. Sipka S, Dey I, Buda C, Csongor J, Szegedi G, Farkas T: The mechanism of inhibitory effect of eicosapentaenoic acid on phagocytic activity and chemotaxis of human neutrophil granulocytes. Clin Immunol Immunopathol. 1996 Jun;79(3):224-8.
10. Miwa H, Yamamoto M, Futata T, Kan K, Asano T: Thin-layer chromatography and high-performance liquid chromatography for the assay of fatty acid compositions of individual phospholipids in platelets from non-insulin-dependent diabetes mellitus patients: effect of eicosapentaenoic acid ethyl ester administration. J Chromatogr B Biomed Appl. 1996 Mar 3;677(2):217-23.
11. Kim HH, Shin CM, Park CH, Kim KH, Cho KH, Eun HC, Chung JH: Eicosapentaenoic acid inhibits UV-induced MMP-1 expression in human dermal fibroblasts. J Lipid Res. 2005 Aug;46(8):1712-20. Epub 2005 Jun 1.
12. Gillis RC, Daley BJ, Enderson BL, Karlstad MD: Eicosapentaenoic acid and gamma-linolenic acid induce apoptosis in HL-60 cells. J Surg Res. 2002 Sep;107(1):145-53.
13. Hino K, Murakami Y, Nagai A, Kitase A, Hara Y, Furutani T, Ren F, Yamaguchi Y, Yutoku K, Yamashita S, Okuda M, Okita M, Okita K: Alpha-tocopherol [corrected] and ascorbic acid attenuates the ribavirin [corrected] induced decrease of eicosapentaenoic acid in erythrocyte membrane in chronic hepatitis C patients. J Gastroenterol Hepatol. 2006 Aug;21(8):1269-75.
14. Takenaga M, Hirai A, Terano T, Tamura Y, Kitagawa H, Yoshida S: Comparison of the in vitro effect of eicosapentaenoic acid (EPA)-derived lipoxygenase metabolites on human platelet function with those of arachidonic acid. Thromb Res. 1986 Feb 1;41(3):373-84.
15. Hereliuk VI: [The role of arachidonic and eicosapentaenoic acid lipoxygenase products in the pathogenesis of generalized parodontosis]. Fiziol Zh. 2000;46(6):112-5.
16. Aas V, Rokling-Andersen MH, Kase ET, Thoresen GH, Rustan AC: Eicosapentaenoic acid (20:5 n-3) increases fatty acid and glucose uptake in cultured human skeletal muscle cells. J Lipid Res. 2006 Feb;47(2):366-74. Epub 2005 Nov 21.
17. Kim HH, Cho S, Lee S, Kim KH, Cho KH, Eun HC, Chung JH: Photoprotective and anti-skin-aging effects of eicosapentaenoic acid in human skin in vivo. J Lipid Res. 2006 May;47(5):921-30. Epub 2006 Feb 7.
18. Herrmann W, Beitz J: [Decreasing atherogenic risks by an eicosapentaenoic acid-rich diet]. Z Gesamte Inn Med. 1987 Mar 1;42(5):117-22.
19. Ide T, Okamura T, Kumashiro R, Koga Y, Hino T, Hisamochi A, Ogata K, Tanaka K, Kuwahara R, Seki R, Sata M: A pilot study of eicosapentaenoic acid therapy for ribavirin-related anemia in patients with chronic hepatitis C. Int J Mol Med. 2003 Jun;11(6):729-32.
20. Francois CA, Connor SL, Bolewicz LC, Connor WE: Supplementing lactating women with flaxseed oil does not increase docosahexaenoic acid in their milk. Am J Clin Nutr. 2003 Jan;77(1):226-33.
21. Dunstan JA, Roper J, Mitoulas L, Hartmann PE, Simmer K, Prescott SL: The effect of supplementation with fish oil during pregnancy on breast milk immunoglobulin A, soluble CD14, cytokine levels and fatty acid composition. Clin Exp Allergy. 2004 Aug;34(8):1237-42.
22. Luostarinen R, Saldeen T: Dietary fish oil decreases superoxide generation by human neutrophils: relation to cyclooxygenase pathway and lysosomal enzyme release. Prostaglandins Leukot Essent Fatty Acids. 1996 Sep;55(3):167-72.
23. Calzada C, Vericel E, Lagarde M: Lower levels of lipid peroxidation in human platelets incubated with eicosapentaenoic acid. Biochim Biophys Acta. 1992 Jul 29;1127(2):147-52.
24. Lagarde M, Croset M, Vericel E, Calzada C: Effects of small concentrations of eicosapentaenoic acid on platelets. J Intern Med Suppl. 1989;731:177-9.
25. Bays HE, Ballantyne CM, Kastelein JJ, Isaacsohn JL, Braeckman RA, Soni PN: Eicosapentaenoic acid ethyl ester (AMR101) therapy in patients with very high triglyceride levels (from the Multi-center, plAcebo-controlled, Randomized, double-blINd, 12-week study with an open-label Extension [MARINE] trial). Am J Cardiol. 2011 Sep 1;108(5):682-90. doi: 10.1016/j.amjcard.2011.04.015. Epub 2011 Jun 16.
26. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=12549599
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=18638380
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30. https://www.ncbi.nlm.nih.gov/pubmed/?term=21118482
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=21274596
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=23920312
33. https://www.ncbi.nlm.nih.gov/pubmed/?term=24108131
34. https://www.ncbi.nlm.nih.gov/pubmed/?term=24238887
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37. https://www.ncbi.nlm.nih.gov/pubmed/?term=9668087