Linoleic acid (CHEM003884)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (6)XML
Record Information
Version1.0
Creation Date2014-09-11 05:22:52 UTC
Update Date2026-03-31 19:12:52 UTC
Accession NumberCHEM003884
Identification
Common NameLinoleic acid
ClassSmall Molecule
DescriptionLinoleic acid is a doubly unsaturated fatty acid, also known as an omega-6 fatty acid, occurring widely in plant glycosides. In this particular polyunsaturated fatty acid (PUFA), the first double bond is located between the sixth and seventh carbon atom from the methyl end of the fatty acid (n-6). Linoleic acid is an essential fatty acid in human nutrition because it cannot be synthesized by humans. It is used in the biosynthesis of prostaglandins (via arachidonic acid) and cell membranes. (From Stedman, 26th ed).
Contaminant Sources
  • Cosmetic Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(9Z,12Z)-Octadecadienoic acidChEBI
(Z,Z)-9,12-Octadecadienoic acidChEBI
9-cis,12-cis-Octadecadienoic acidChEBI
9Z,12Z-Octadecadienoic acidChEBI
Acide cis-linoleiqueChEBI
Acide linoleiqueChEBI
Acido linoleicoChEBI
all-cis-9,12-Octadecadienoic acidChEBI
C18:2 9C, 12C Omega6 todos cis-9,12-octadienoicoChEBI
C18:2, N-6,9 all-cisChEBI
cis,cis-9,12-Octadecadienoic acidChEBI
cis,cis-Linoleic acidChEBI
cis-Delta(9,12)-Octadecadienoic acidChEBI
LAChEBI
Linolic acidChEBI
9-cis,12-cis-OctadecadienoateKegg
(9Z,12Z)-OctadecadienoateGenerator
(Z,Z)-9,12-OctadecadienoateGenerator
9Z,12Z-OctadecadienoateGenerator
all-cis-9,12-OctadecadienoateGenerator
cis,cis-9,12-OctadecadienoateGenerator
cis,cis-LinoleateGenerator
cis-delta(9,12)-OctadecadienoateGenerator
cis-Δ(9,12)-octadecadienoateGenerator
cis-Δ(9,12)-octadecadienoic acidGenerator
LinolateGenerator
LinoleateGenerator
(9Z,12Z)-9,12-OctadecadienoateHMDB
(9Z,12Z)-9,12-Octadecadienoic acidHMDB
9-cis,12-cis-LinoleateHMDB
9-cis,12-cis-Linoleic acidHMDB
9Z,12Z-LinoleateHMDB
9Z,12Z-Linoleic acidHMDB
cis-9,cis-12-OctadecadienoateHMDB
cis-9,cis-12-Octadecadienoic acidHMDB
cis-D9,12-OctadecadienoateHMDB
cis-D9,12-Octadecadienoic acidHMDB
Emersol 315HMDB
Extra linoleic 90HMDB
Polylin 515HMDB
Unifac 6550HMDB
Acid, 9,12-octadecadienoicHMDB
Linoelaidic acidHMDB
Linoleic acid, (e,e)-isomerHMDB
Linoleic acid, (Z,Z)-isomerHMDB
Linoleic acid, (Z,Z)-isomer, 14C-labeledHMDB
Linoleic acid, ammonium salt, (Z,Z)-isomerHMDB
Linoleic acid, potassium salt, (Z,Z)-isomerHMDB
9 trans,12 trans Octadecadienoic acidHMDB
9-trans,12-trans-Octadecadienoic acidHMDB
Linoleic acid, sodium salt, (e,e)-isomerHMDB
Linoleic acid, sodium salt, (Z,Z)-isomerHMDB
trans,trans-9,12-Octadecadienoic acidHMDB
9,12-Octadecadienoic acidHMDB
Linoelaidic acid, (e,Z)-isomerHMDB
Linoleic acid, calcium salt, (Z,Z)-isomerHMDB
Linolelaidic acidHMDB
9,12 Octadecadienoic acidHMDB
Linoleic acid, (Z,e)-isomerHMDB
FA(18:2(9Z,12Z))HMDB
Chemical FormulaC18H32O2
Average Molecular Mass280.446 g/mol
Monoisotopic Mass280.240 g/mol
CAS Registry Number60-33-3
IUPAC Name(9Z,12Z)-octadeca-9,12-dienoic acid
Traditional Namelinoleic
SMILESCCCCC\C=C/C\C=C/CCCCCCCC(O)=O
InChI IdentifierInChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-
InChI KeyOYHQOLUKZRVURQ-HZJYTTRNSA-N
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
Substituents
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Adipose Tissue
  • Erythrocyte
  • Fibroblasts
  • Intestine
  • Kidney
  • Muscle
  • Myelin
  • Placenta
  • Platelet
  • Prostate
  • Skin
  • Spleen
  • Stratum Corneum
Pathways
NameSMPDB LinkKEGG Link
Alpha Linolenic Acid and Linoleic Acid MetabolismSMP00018 map00592
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-8.5 °C
Boiling Point230°C
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00015 g/LALOGPS
logP7.06ALOGPS
logP6.42ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity88.52 m³·mol⁻¹ChemAxon
Polarizability35.86 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-000t-7900000000-b6ee03c4800464c37471Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-00vi-9300000000-c92dac639ced59eb5dbeSpectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-003s-9700000000-77e67d7b1a161e6ecfa6Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000t-7900000000-b6ee03c4800464c37471Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00vi-9300000000-c92dac639ced59eb5dbeSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-003s-9700000000-77e67d7b1a161e6ecfa6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9750000000-50d69948d56dd2ba6e42Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9631000000-cc93c24bbf14d81ae9b6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0f89-0190000000-2be9501b1d4a9fcbd1c0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0uk9-0790000000-7f6e35a591f977bc488eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-0090000000-c56edc2bbf9d6752aec5Spectrum
LC-MS/MSLC-MS/MS Spectrum - FAB-EBEB (JMS-HX/HX 110A, JEOL) , Negativesplash10-004i-0090000000-baf4579e26c6b393d391Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0090000000-815c1682b2c59ba96f10Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-0090000000-3406b2b2d5756807e1cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-0090000000-2fb4975278fa4d118f43Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a6r-9380000000-37f833673c248405c8efSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9200000000-7d34ed5900a17ffe3f9bSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090010000-f8df6099e003402f2566Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0091021000-0e44779958d5744d873bSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0091021000-0e44779958d5744d873bSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0091021000-0e44779958d5744d873bSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0091021000-0e44779958d5744d873bSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090010000-f8df6099e003402f2566Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0091021000-0e44779958d5744d873bSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-adbf36f0a17c33ac33f8Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0090000000-2747c83af78732eb6e16Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0090000000-a0415b1cb63b4562b40eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-8bdf8d54a29f73494242Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0239-4590000000-e5ee57553b064eae2efeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rf-9830000000-b26ba057a2b4d135b478Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-f1e9e4b543f7d4f48bf8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ti-0090000000-665523c6142ff4e39c96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9240000000-dca36a25ad7519d500c3Spectrum
MSMass Spectrum (Electron Ionization)splash10-015a-9200000000-a193c27810bedf93c498Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000673
FooDB IDFDB006287
Phenol Explorer IDNot Available
KNApSAcK IDC00001224
BiGG ID37956
BioCyc IDLINOLEIC_ACID
METLIN ID191
PDB IDNot Available
Wikipedia LinkLinoleic_acid
Chemspider ID4444105
ChEBI ID17351
PubChem Compound ID5280450
Kegg Compound IDC01595
YMDB IDNot Available
ECMDB IDM2MDB004733
References
Synthesis ReferenceWalborsky, Harry M.; Davis, Robert H.; Howton, David R. A total synthesis of linoleic acid. Journal of the American Chemical Society (1951), 73 2590-4.
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11113630
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11304127
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11322990
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=14667063
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=14993245
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=15115315
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=15642793
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=15969511
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=16254037
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=16563718
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=17647039
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=18044828
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=18990554
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=19628674
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=19936816
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23900039
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=24081493
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=6205897
19. Walborsky, Harry M.; Davis, Robert H.; Howton, David R. A total synthesis of linoleic acid. Journal of the American Chemical Society (1951), 73 2590-4.
20. Schurer NY, Stremmel W, Grundmann JU, Schliep V, Kleinert H, Bass NM, Williams ML: Evidence for a novel keratinocyte fatty acid uptake mechanism with preference for linoleic acid: comparison of oleic and linoleic acid uptake by cultured human keratinocytes, fibroblasts and a human hepatoma cell line. Biochim Biophys Acta. 1994 Feb 10;1211(1):51-60.
21. Valianpour F, Wanders RJ, Overmars H, Vaz FM, Barth PG, van Gennip AH: Linoleic acid supplementation of Barth syndrome fibroblasts restores cardiolipin levels: implications for treatment. J Lipid Res. 2003 Mar;44(3):560-6. Epub 2002 Dec 16.
22. Horrobin DF: Essential fatty acid metabolism and its modification in atopic eczema. Am J Clin Nutr. 2000 Jan;71(1 Suppl):367S-72S.
23. Imokawa G, Yada Y, Higuchi K, Okuda M, Ohashi Y, Kawamata A: Pseudo-acylceramide with linoleic acid produces selective recovery of diminished cutaneous barrier function in essential fatty acid-deficient rats and has an inhibitory effect on epidermal hyperplasia. J Clin Invest. 1994 Jul;94(1):89-96.
24. Kawajiri H, Hsi LC, Kamitani H, Ikawa H, Geller M, Ward T, Eling TE, Glasgow WC: Arachidonic and linoleic acid metabolism in mouse intestinal tissue: evidence for novel lipoxygenase activity. Arch Biochem Biophys. 2002 Feb 1;398(1):51-60.
25. Iso H, Sato S, Umemura U, Kudo M, Koike K, Kitamura A, Imano H, Okamura T, Naito Y, Shimamoto T: Linoleic acid, other fatty acids, and the risk of stroke. Stroke. 2002 Aug;33(8):2086-93.
26. Seidel D, Heipertz R, Weisner B: Cerebrospinal fluid lipids in demyelinating disease. II. Linoleic acid as an index of impaired blood-CSF barrier. J Neurol. 1980 Jan;222(3):177-82.
27. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69.
28. Salo P, Seppanen-Laakso T, Laakso I, Seppanen R, Niinikoski H, Viikari J, Simell O: Low-saturated fat, low-cholesterol diet in 3-year-old children: effect on intake and composition of trans fatty acids and other fatty acids in serum phospholipid fraction-The STRIP study. Special Turku coronary Risk factor Intervention Project for children. J Pediatr. 2000 Jan;136(1):46-52.
29. Grimsgaard S, Bonaa KH, Jacobsen BK, Bjerve KS: Plasma saturated and linoleic fatty acids are independently associated with blood pressure. Hypertension. 1999 Sep;34(3):478-83.
30. 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.
31. 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.