Arachidonic acid (CED0000922)

Record Information
Version1.0
Creation Date2016-05-25 02:49:15 UTC
Update Date2026-05-14 18:09:05 UTC
Accession NumberCHEM020983
Identification
Common NameArachidonic acid
ClassSmall Molecule
Description
Arachidonic acid belongs to the fatty acids and conjugates, a subclass of fatty acyls within the organic compounds. This lipid-like molecule has the chemical formula C20H32O2 and an average molecular weight of 304.47 g/mol. Industrially, the compound is utilized as a conditioner and softener. The substance is released from plastics, specifically polystyrene and polypropylene. It has been recorded in three distinct sources: antennas within electrical and electronic equipment, food contact materials used in food processing and cookware, and indoor air, dust, and atmospheric transport. Exposure to arachidonic acid can occur through oral, inhalation, and touch routes. At the molecular level, arachidonic acid interacts with five recorded protein targets. It serves as a ligand or inhibitor for Prostaglandin G/H synthase 1 (PTGS1), the 14 kDa fatty acid-binding protein, the bile acid receptor (NR1H4), and the peroxisome proliferator-activated receptor alpha (PPARA), in addition to one other protein.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoic acidChEBI
(5Z,8Z,11Z,14Z)-Icosatetraenoic acidChEBI
AAChEBI
all-cis-5,8,11,14-Eicosatetraenoic acidChEBI
ARAChEBI
ArachidonateChEBI
ArachidonsaeureChEBI
cis-5,8,11,14-Eicosatetraenoic acidChEBI
cis-Delta(5,8,11,14)-Eicosatetraenoic acidChEBI
5Z,8Z,11Z,14Z-Eicosatetraenoic acidKegg
(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acidKegg
(5Z,8Z,11Z,14Z)-5,8,11,14-IcosatetraenoateGenerator
(5Z,8Z,11Z,14Z)-IcosatetraenoateGenerator
all-cis-5,8,11,14-EicosatetraenoateGenerator
cis-5,8,11,14-EicosatetraenoateGenerator
cis-delta(5,8,11,14)-EicosatetraenoateGenerator
cis-Δ(5,8,11,14)-eicosatetraenoateGenerator
cis-Δ(5,8,11,14)-eicosatetraenoic acidGenerator
5Z,8Z,11Z,14Z-EicosatetraenoateGenerator
(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoateGenerator
Arachidonic acid, (all-Z)-isomer, 1-(14)C-labeledMeSH
Arachidonic acid, zinc salt, (all-Z)-isomerMeSH
Sodium arachidonateMeSH
Arachidonate, sodiumMeSH
Arachidonic acid, (all-Z)-isomer, 3H-labeledMeSH
Arachidonic acid, ammonium salt, (all-Z)-isomerMeSH
Arachidonic acid, cerium salt, (all-Z)-isomerMeSH
Arachidonic acid, sodium saltMeSH
Arachidonic acid, sodium salt, (all-Z)-isomerMeSH
Vitamin FMeSH
Arachidonic acid, cesium salt, (all-Z)-isomerMeSH
Arachidonic acid, lithium salt, (all-Z)-isomerMeSH
(all-Z)-5,8,11,14-Eicosatetraenoic acidMeSH
Arachidonic acid, potassium salt, (all-Z)-isomerMeSH
(all-Z)-5,8,11,14-EicosatetraenoateHMDB
5,8,11,14-all-cis-EicosatetraenoateHMDB
5,8,11,14-all-cis-Eicosatetraenoic acidHMDB
5,8,11,14-EicosatetraenoateHMDB
5,8,11,14-Eicosatetraenoic acidHMDB
5-cis,8-cis,11-cis,14-cis-EicosatetraenoateHMDB
5-cis,8-cis,11-cis,14-cis-Eicosatetraenoic acidHMDB
cis-D5,8,11,14-EicosatetraenoateHMDB
cis-D5,8,11,14-Eicosatetraenoic acidHMDB
ImmunocytophyteHMDB
FA(20:4(5Z,8Z,11Z,14Z))HMDB
FA(20:4n6)HMDB
Chemical FormulaC20H32O2
Average Molecular Mass304.467 g/mol
Monoisotopic Mass304.240 g/mol
CAS Registry Number506-32-1
IUPAC Name(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
Traditional Namearachidonic acid
SMILESCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI IdentifierInChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-
InChI KeyYZXBAPSDXZZRGB-DOFZRALJSA-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 Solubility0.00015 g/LALOGPS
logP6.8ALOGPS
logP6.59ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity99.95 m³·mol⁻¹ChemAxon
Polarizability37.2 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 Spectrumsplash10-005c-9800000000-87c290971fc8a628fb23Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-005c-9800000000-87c290971fc8a628fb23Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0006-6900000000-6870df266b6c73f2a4a1Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-7390000000-7004b9cd28a9b3d9c991Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-05i9-9252000000-475d13959ee8ce889646Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0nmi-0913000000-95846e8d5e8afd29664bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-005l-0902100000-6fc8730bd28daa779b66Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-005l-0902100000-6fc8730bd28daa779b66Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-005l-0902100000-6fc8730bd28daa779b66Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0009000000-4dd23c77f8e48c0ab9ecNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0009000000-4dd23c77f8e48c0ab9ecNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0009000000-6bd9d0477c122d3eed94Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0009000000-510ea33e558fa238a1d2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0009000000-73a6b21464acba15463cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0009000000-4dd23c77f8e48c0ab9ecNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0049000000-102d050109d3c78b1a25Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0090000000-2fb9003e782ec3d05e20Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0nmi-0913000000-95846e8d5e8afd29664bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0009000000-6bd9d0477c122d3eed94Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0009000000-510ea33e558fa238a1d2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0049000000-102d050109d3c78b1a25Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0009000000-6bd9d0477c122d3eed94Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0009000000-510ea33e558fa238a1d2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-1934000000-3fb5938d1b4795217a97Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-1029000000-a3a682a45d7fab319c13Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0049000000-102d050109d3c78b1a25Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4r-1196000000-a42ea66033eb9771d36dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4j-5691000000-2bc7b1ae5487233dfce8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0007-7950000000-b15a8d382a4b3ad62d08Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0029000000-28a9bbfed5fabd10c0c2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zfr-2079000000-3f6e64ef7522a793e9a9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9130000000-9c0c8bb5fc8e30bf53c7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4r-3696000000-fac338f07343ba79c461Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-008c-6920000000-b3db7333dbb8d5ffd163Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05nf-9400000000-cf0b801f97b61f93efecNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0019000000-e301ae96559ee65daa0eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udr-2169000000-0a6a29db3ed8f6ce566fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006x-9220000000-b438233576b843156a7bNot 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
7059.0Log mg/kg[4000:13000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
19Indoor airAir, dust & atmospheric transportNot Available
490Personal care & cosmeticsNot Available
494Food contact materialsFood, food processing & cookwareNot Available
506AntennasElectrical & Electronic EquipmentNot Available
Pathways
146 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Peroxisome proliferator-activated receptor gamma structureClick to view 3D structurePeroxisome proliferator-activated receptor gammaP37231HumansPredicted (SEA)0.155698
Peroxisome proliferator-activated receptor alpha structureClick to view 3D structurePeroxisome proliferator-activated receptor alphaQ07869HumansPredicted (SEA)0.155698
Peroxisome proliferator-activated receptor delta structureClick to view 3D structurePeroxisome proliferator-activated receptor deltaQ03181HumansPredicted (SEA)0.155698
Click to view 3D structureTransient receptor potential cation channel subfamily V member 2Q9WUD2Rattus norvegicusPredicted (SEA)0.467095
Fatty acid-binding protein, adipocyte structureClick to view 3D structureFatty acid-binding protein, adipocyteP15090HumansPredicted (SEA)0.233548
Click to view 3D structureFatty-acid amide hydrolase 1O00519HumansPredicted (SEA)1.40129
Tyrosine-protein phosphatase non-receptor type 1 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 1P18031HumansPredicted (SEA)1.55698
Click to view 3D structureCannabinoid receptor 1P20272Rattus norvegicusPredicted (SEA)1.79053
Click to view 3D structureOxoeicosanoid receptor 1Q8TDS5HumansPredicted (SEA)0.0778492
Cannabinoid receptor 2 structureClick to view 3D structureCannabinoid receptor 2P34972HumansPredicted (SEA)2.02408
Cannabinoid receptor 1 structureClick to view 3D structureCannabinoid receptor 1P21554HumansPredicted (SEA)3.26967
Free fatty acid receptor 4 structureClick to view 3D structureFree fatty acid receptor 4Q5NUL3HumansPredicted (SEA)0.233548
Click to view 3D structureCannabinoid receptor 2P47936Mus musculusPredicted (SEA)1.08989
Click to view 3D structureFatty-acid amide hydrolase 1P97612Rattus norvegicusPredicted (SEA)3.34752
Click to view 3D structureCannabinoid receptor 2Q9QZN9Rattus norvegicusPredicted (SEA)0.544945
Free fatty acid receptor 1 structureClick to view 3D structureFree fatty acid receptor 1O14842HumansPredicted (SEA)1.16774
Click to view 3D structureCannabinoid receptor 1P47746Mus musculusPredicted (SEA)0.622794
Transient receptor potential cation channel subfamily V member 1 structureClick to view 3D structureTransient receptor potential cation channel subfamily V member 1Q8NER1HumansPredicted (SEA)2.33548
Click to view 3D structureTransient receptor potential cation channel subfamily V member 1O35433Rattus norvegicusPredicted (SEA)1.47914
G-protein coupled receptor 84 structureClick to view 3D structureG-protein coupled receptor 84Q9NQS5HumansPredicted (SEA)2.17978
Click to view 3D structureHistone deacetylase 11Q96DB2HumansPredicted (SEA)10.9767
Fatty acid-binding protein, heart structureClick to view 3D structureFatty acid-binding protein, heartP05413HumansPredicted (SEA)0.544945
Click to view 3D structureSolute carrier organic anion transporter family member 2A1Q9EPT5Mus musculusPredicted (SEA)0.544945
Click to view 3D structureProstaglandin G/H synthase 2P79208Ovis ariesPredicted (SEA)1.55698
Click to view 3D structureFatty-acid amide hydrolase 1O08914Mus musculusPredicted (SEA)10.3539
Concentrations
Not Available
External Links
DrugBank IDDB04557
HMDB IDHMDB0001043
FooDB IDFDB011872
Phenol Explorer IDNot Available
KNApSAcK IDC00000388
BiGG ID1586189
BioCyc IDARACHIDONIC_ACID
METLIN ID193
PDB IDNot Available
Wikipedia LinkArachidonic_acid
Chemspider ID392692
ChEBI ID15843
PubChem Compound ID444899
Kegg Compound IDC00219
YMDB IDNot Available
ECMDB IDM2MDB004816
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Dai, Chuanchao; Yuan, Zhilin; Wang, Anqi. Production of arachidonic acid and eicosapentaenoic acid with organic wastewater of soybean products. Zhongguo Youzhi (2004), 29(5), 31-33.
2. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762.
3. Markuszewski L, Rosiak M, Golanski J, Rysz J, Spychalska M, Watala C: Reduced blood platelet sensitivity to aspirin in coronary artery disease: are dyslipidaemia and inflammatory states possible factors predisposing to sub-optimal platelet response to aspirin? Basic Clin Pharmacol Toxicol. 2006 May;98(5):503-9.
4. Frelinger AL 3rd, Furman MI, Linden MD, Li Y, Fox ML, Barnard MR, Michelson AD: Residual arachidonic acid-induced platelet activation via an adenosine diphosphate-dependent but cyclooxygenase-1- and cyclooxygenase-2-independent pathway: a 700-patient study of aspirin resistance. Circulation. 2006 Jun 27;113(25):2888-96. Epub 2006 Jun 19.
5. Daskalou T, Karamouzis M, Liaros G: [Metabolites of arachidonic acid in activating platelets and their estimation by radionuclide techniques]. Hell J Nucl Med. 2006 Jan-Apr;9(1):49-52.
6. Sacerdoti D, Gatta A, McGiff JC: Role of cytochrome P450-dependent arachidonic acid metabolites in liver physiology and pathophysiology. Prostaglandins Other Lipid Mediat. 2003 Oct;72(1-2):51-71.
7. Claria J, Arroyo V: Prostaglandins and other cyclooxygenase-dependent arachidonic acid metabolites and the kidney in liver disease. Prostaglandins Other Lipid Mediat. 2003 Oct;72(1-2):19-33.
8. Pantaleo P, Marra F, Vizzutti F, Spadoni S, Ciabattoni G, Galli C, La Villa G, Gentilini P, Laffi G: Effects of dietary supplementation with arachidonic acid on platelet and renal function in patients with cirrhosis. Clin Sci (Lond). 2004 Jan;106(1):27-34.
9. Hughes-Fulford M, Tjandrawinata RR, Li CF, Sayyah S: Arachidonic acid, an omega-6 fatty acid, induces cytoplasmic phospholipase A2 in prostate carcinoma cells. Carcinogenesis. 2005 Sep;26(9):1520-6. Epub 2005 May 5.
10. Kudolo GB, Wang W, Barrientos J, Elrod R, Blodgett J: The ingestion of Ginkgo biloba extract (EGb 761) inhibits arachidonic acid-mediated platelet aggregation and thromboxane B2 production in healthy volunteers. J Herb Pharmacother. 2004;4(4):13-26.
11. Burke J, Kraft WK, Greenberg HE, Gleave M, Pitari GM, VanBuren S, Wagner JA, Waldman SA: Relationship of arachidonic acid concentration to cyclooxygenase-dependent human platelet aggregation. J Clin Pharmacol. 2003 Sep;43(9):983-9.
12. Carroll RC, Craft RM, Chavez JJ, Snider CC, Bresee SJ, Cohen E: A Thrombelastograph whole blood assay for clinical monitoring of NSAID-insensitive transcellular platelet activation by arachidonic acid. J Lab Clin Med. 2005 Jul;146(1):30-5.
13. Cuisset T, Frere C, Quilici J, Barbou F, Morange PE, Hovasse T, Bonnet JL, Alessi MC: High post-treatment platelet reactivity identified low-responders to dual antiplatelet therapy at increased risk of recurrent cardiovascular events after stenting for acute coronary syndrome. J Thromb Haemost. 2006 Mar;4(3):542-9. Epub 2005 Dec 22.
14. Arruzazabala ML, Mas R, Molina V, Carbajal D, Fernandez L, Illnait J, Castano G, Fernandez J, Mendoza S: Effects of d-003, a new substance purified from sugar cane wax, on platelet aggregation and plasma levels of arachidonic acid metabolites in healthy volunteers. Int J Clin Pharmacol Res. 2004;24(2-3):55-63.
15. Sinzinger H: Metabolites of arachidonic acid in activating platelets and their estimation by radionuclide techniques. Hell J Nucl Med. 2006 May-Aug;9(2):111; author reply 111-2.
16. Bringmann A, Schopf S, Faude F, Reichenbach A: Arachidonic acid-induced inhibition of Ca2+ channel currents in retinal glial (Muller) cells. Graefes Arch Clin Exp Ophthalmol. 2001 Nov;239(11):859-64.
17. Eikelboom JW, Hankey GJ, Thom J, Claxton A, Yi Q, Gilmore G, Staton J, Barden A, Norman PE: Enhanced antiplatelet effect of clopidogrel in patients whose platelets are least inhibited by aspirin: a randomized crossover trial. J Thromb Haemost. 2005 Dec;3(12):2649-55.
18. Cox D, Maree AO, Dooley M, Conroy R, Byrne MF, Fitzgerald DJ: Effect of enteric coating on antiplatelet activity of low-dose aspirin in healthy volunteers. Stroke. 2006 Aug;37(8):2153-8. Epub 2006 Jun 22.
19. Yamada N, Miyamoto M, Isogaya M, Suzuki M, Ikezawa S, Ohno M, Otake A, Umemura K: TRA-418, a novel compound having both thromboxane A(2) receptor antagonistic and prostaglandin I(2) receptor agonistic activities: its antiplatelet effects in human and animal platelets. J Thromb Haemost. 2003 Aug;1(8):1813-9.
20. Payne DA, Jones CI, Hayes PD, Webster SE, Ross Naylor A, Goodall AH: Platelet inhibition by aspirin is diminished in patients during carotid surgery: a form of transient aspirin resistance? Thromb Haemost. 2004 Jul;92(1):89-96.
21. Kroetz DL, Xu F: Regulation and inhibition of arachidonic acid omega-hydroxylases and 20-HETE formation. Annu Rev Pharmacol Toxicol. 2005;45:413-38.
22. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3.
23. Pompeia C, Lima T, Curi R: Arachidonic acid cytotoxicity: can arachidonic acid be a physiological mediator of cell death? Cell Biochem Funct. 2003 Jun;21(2):97-104.
24. Calder PC: Long-chain n-3 fatty acids and inflammation: potential application in surgical and trauma patients. Braz J Med Biol Res. 2003 Apr;36(4):433-46. Epub 2003 Apr 8.
25. Zhao X, Imig JD: Kidney CYP450 enzymes: biological actions beyond drug metabolism. Curr Drug Metab. 2003 Feb;4(1):73-84.
26. Kudo I, Murakami M: Phospholipase A2 enzymes. Prostaglandins Other Lipid Mediat. 2002 Aug;68-69:3-58.
27. Yang P, Cartwright C, Chan D, Ding J, Felix E, Pan Y, Pang J, Rhea P, Block K, Fischer SM, Newman RA: Anticancer activity of fish oils against human lung cancer is associated with changes in formation of PGE2 and PGE3 and alteration of Akt phosphorylation. Mol Carcinog. 2014 Jul;53(7):566-77. doi: 10.1002/mc.22008. Epub 2013 Jan 31.
28. Ren R, Hashimoto T, Mizuno M, Takigawa H, Yoshida M, Azuma T, Kanazawa K: A lipid peroxidation product 9-oxononanoic acid induces phospholipase A2 activity and thromboxane A2 production in human blood. J Clin Biochem Nutr. 2013 May;52(3):228-33. doi: 10.3164/jcbn.12-110. Epub 2013 May 1.
29. Kleinstein SE, Heath L, Makar KW, Poole EM, Seufert BL, Slattery ML, Xiao L, Duggan DJ, Hsu L, Curtin K, Koepl L, Muehling J, Taverna D, Caan BJ, Carlson CS, Potter JD, Ulrich CM: Genetic variation in the lipoxygenase pathway and risk of colorectal neoplasia. Genes Chromosomes Cancer. 2013 May;52(5):437-49. doi: 10.1002/gcc.22042. Epub 2013 Feb 12.
30. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
31. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
32. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
33. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
34. 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.
35. The lipid handbook with CD-ROM
36. Dai, Chuanchao; Yuan, Zhilin; Wang, Anqi. Production of arachidonic acid and eicosapentaenoic acid with organic wastewater of soybean products. Zhongguo Youzhi (2004), 29(5), 31-33.
37. 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.
38. van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21.
39. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386
40. 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
41. 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
42. https://www.ncbi.nlm.nih.gov/pubmed/?term=15129302
43. https://www.ncbi.nlm.nih.gov/pubmed/?term=18931599
44. https://www.ncbi.nlm.nih.gov/pubmed/?term=18973997
45. https://www.ncbi.nlm.nih.gov/pubmed/?term=25584012
46. https://www.ncbi.nlm.nih.gov/pubmed/?term=2820055