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Showing Compound Linonelic acid (FDB006562)

Record Information
Version1.0
Creation date2010-04-08 22:07:12 UTC
Update date2019-11-26 03:01:11 UTC
Primary IDFDB006562
Secondary Accession Numbers
  • FDB006287
  • FDB030981
Chemical Information
FooDB NameLinonelic acid
DescriptionLinoleate, also known as (9z,12z)-octadecadienoic acid or cis,cis-linoleic acid, belongs to lineolic acids and derivatives class of compounds. Those 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. Thus, linoleate is considered to be a fatty acid lipid molecule. Linoleate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Linoleate can be found in a number of food items such as pecan nut, onion-family vegetables, red huckleberry, and romaine lettuce, which makes linoleate a potential biomarker for the consumption of these food products. Linoleate can be found primarily in most biofluids, including saliva, urine, feces, and blood, as well as throughout most human tissues. In humans, linoleate is involved in the alpha linolenic acid and linoleic acid metabolism. Moreover, linoleate is found to be associated with hypertension, cirrhosis, schizophrenia, and gestational diabetes. Linoleate is a non-carcinogenic (not listed by IARC) potentially toxic compound. Linoleic acid (LA), a carboxylic acid, is a polyunsaturated omega-6 fatty acid, an 18-carbon chain with two double bonds in cis configuration. A shorthand notation like "18:2 (n-6)" or "18:2 cis-9,12" may be used in literature. It typically occurs in nature as a triglyceride ester; free fatty acids are typically low in foods .
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(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
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H32O2
IUPAC name(9Z,12Z)-octadeca-9,12-dienoic acid
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
Isomeric SMILESCCCCC\C=C/C\C=C/CCCCCCCC(O)=O
Average Molecular Weight280.4455
Monoisotopic Molecular Weight280.240230268
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-015a-9200000000-a193c27810bedf93c4982014-09-20View Spectrum
GC-MSalpha-Linoleic acid, 1 TMS, GC-MS Spectrumsplash10-000t-7900000000-b6ee03c4800464c37471Spectrum
GC-MSalpha-Linoleic acid, 1 TMS, GC-MS Spectrumsplash10-00vi-9300000000-c92dac639ced59eb5dbeSpectrum
GC-MSalpha-Linoleic acid, 1 TMS, GC-MS Spectrumsplash10-003s-9700000000-77e67d7b1a161e6ecfa6Spectrum
GC-MSalpha-Linoleic acid, non-derivatized, GC-MS Spectrumsplash10-000t-7900000000-b6ee03c4800464c37471Spectrum
GC-MSalpha-Linoleic acid, non-derivatized, GC-MS Spectrumsplash10-00vi-9300000000-c92dac639ced59eb5dbeSpectrum
GC-MSalpha-Linoleic acid, non-derivatized, GC-MS Spectrumsplash10-003s-9700000000-77e67d7b1a161e6ecfa6Spectrum
Predicted GC-MSalpha-Linoleic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0007-9750000000-50d69948d56dd2ba6e42Spectrum
Predicted GC-MSalpha-Linoleic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-9631000000-cc93c24bbf14d81ae9b6Spectrum
Predicted GC-MSalpha-Linoleic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSalpha-Linoleic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0f89-0190000000-2be9501b1d4a9fcbd1c02012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0uk9-0790000000-7f6e35a591f977bc488e2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-0090000000-c56edc2bbf9d6752aec52012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - FAB-EBEB (JMS-HX/HX 110A, JEOL) , Negativesplash10-004i-0090000000-baf4579e26c6b393d3912012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0090000000-815c1682b2c59ba96f102012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-0090000000-3406b2b2d5756807e1cd2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-0090000000-2fb4975278fa4d118f432012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a6r-9380000000-37f833673c248405c8ef2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9200000000-7d34ed5900a17ffe3f9b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090010000-f8df6099e003402f25662017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0091021000-0e44779958d5744d873b2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0091021000-0e44779958d5744d873b2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0091021000-0e44779958d5744d873b2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0091021000-0e44779958d5744d873b2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090010000-f8df6099e003402f25662017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0091021000-0e44779958d5744d873b2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-adbf36f0a17c33ac33f82017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0090000000-2747c83af78732eb6e162017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0090000000-a0415b1cb63b4562b40e2017-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-8bdf8d54a29f734942422017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0239-4590000000-e5ee57553b064eae2efe2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rf-9830000000-b26ba057a2b4d135b4782017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-f1e9e4b543f7d4f48bf82017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ti-0090000000-665523c6142ff4e39c962017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9240000000-dca36a25ad7519d500c32017-09-01View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDLINONELIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).