Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110756
Identification
Name: linoleate
Description:An octadecadienoate with cis- double bonds at the 9- and 12- positions; the conjugate base of linoleic acid.
Structure
Thumb
Synonyms:
  • cis,cis-9,12-octadecadienoate
  • 9-cis,12-cis-octadecadienoate
  • linoleic acid
  • 9,12-linoleic acid
  • (9Z,12Z)-octadeca-9,12-dienoate
Chemical Formula: C18H31O2
Average Molecular Weight: 279.44
Monoisotopic Molecular Weight: 280.2402302714
InChI Key: OYHQOLUKZRVURQ-HZJYTTRNSA-M
InChI: InChI=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)/p-1/b7-6-,10-9-
CAS number: 60-33-3
IUPAC Name:(9Z,12Z)-octadeca-9,12-dienoate
Traditional IUPAC Name: linoleic
SMILES:CCCCCC=CCC=CCCCCCCCC([O-])=O
Chemical Taxonomy
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassLineolic acids and derivatives
Direct Parent Lineolic 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
  • Organic anion
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
  • a long-chain fatty acid, an unsaturated fatty acid (LINOLEIC_ACID)
Physical Properties
State: Liquid
Charge:-1
Melting point: -8.5 °C
Experimental Properties:
PropertyValueReference
Melting Point-8.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP7.05SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.000154 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity88.52 m3·mol-1ChemAxon
Polarizability35.86 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
  • Alpha Linolenic Acid and Linoleic Acid Metabolism pae00592
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-000t-7900000000-b6ee03c4800464c37471View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-00vi-9300000000-c92dac639ced59eb5dbeView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-003s-9700000000-77e67d7b1a161e6ecfa6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0f89-0190000000-2be9501b1d4a9fcbd1c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0uk9-0790000000-7f6e35a591f977bc488eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-0090000000-c56edc2bbf9d6752aec5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - FAB-EBEB (JMS-HX/HX 110A, JEOL) , Negativesplash10-004i-0090000000-baf4579e26c6b393d391View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0090000000-815c1682b2c59ba96f10View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-0090000000-3406b2b2d5756807e1cdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-0090000000-2fb4975278fa4d118f43View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a6r-9380000000-37f833673c248405c8efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9200000000-7d34ed5900a17ffe3f9bView in MoNA
MSMass Spectrum (Electron Ionization)splash10-015a-9200000000-a193c27810bedf93c498View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • 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. [19212411 ]
  • 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. [8412012 ]
  • 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. [8123682 ]
  • 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. [12562862 ]
  • Horrobin DF: Essential fatty acid metabolism and its modification in atopic eczema. Am J Clin Nutr. 2000 Jan;71(1 Suppl):367S-72S. [10617999 ]
  • 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. [8040295 ]
  • 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. [11811948 ]
  • 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. [12154268 ]
  • 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. [6153705 ]
  • 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. [10636973 ]
  • 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. [10489397 ]
Synthesis Reference: 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.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CAS60-33-3
ChEBI30245
ChemSpider4573899
HMDBHMDB00673
KEGGC01595
LIPID MAPSLMFA01030120
MetaboLightsMTBLC30245
NCI281243
PubChem5460332
WikipediaLinoleic_acid