Record Information
Version1.0
Creation date2011-09-21 00:36:02 UTC
Update date2019-11-26 03:21:10 UTC
Primary IDFDB023868
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLinoelaidic acid
DescriptionLinoelaidic acid is an isomer of linoleic acid, or conjugated linoleic acid (CLA), a derivative of a fatty acid linoleic acid. Conjugated linoleic acid (CLA) isomers, a group of positional and geometric isomers of linoleic acid [18:2(n-6)], have been studied extensively due to their ability to modulate cancer, atherosclerosis, obesity, immune function and diabetes in a variety of experimental models. CLA's ability to modulate human obesity remains controversial because data from clinical trials using mixed isomers are conflicting. (PMID 10759137) Trans fatty acids are characteristically produced during industrial hydrogenation of plant oils. [HMDB]. Linoelaidic acid is found in green zucchini, green bell pepper, and red bell pepper.
CAS Number506-21-8
Structure
Thumb
Synonyms
SynonymSource
18:2, N-6,9 all-transChEBI
9E,12E-Octadecadienoic acidChEBI
C18:2, N-6,9 all-transChEBI
trans-9,trans-12-Linoleic acidChEBI
9E,12E-OctadecadienoateGenerator
trans-9,trans-12-LinoleateGenerator
LinoelaidateGenerator
(9E,12E)-9,12-OctadecadienoateHMDB
(9E,12E)-9,12-Octadecadienoic acidHMDB
9,12-Octadecadienoic acidMeSH, HMDB
Linoleic acidMeSH, HMDB
Linoleic acid, (Z,Z)-isomer, 14C-labeledMeSH, HMDB
Linolelaidic acidMeSH, HMDB
cis,cis-9,12-Octadecadienoic acidMeSH, HMDB
Linoleic acid, (e,e)-isomerMeSH, HMDB
Linoleic acid, (Z,Z)-isomerMeSH, HMDB
Linoleic acid, ammonium salt, (Z,Z)-isomerMeSH, HMDB
Linoleic acid, potassium salt, (Z,Z)-isomerMeSH, HMDB
Linoelaidic acid, (e,Z)-isomerMeSH, HMDB
9 trans,12 trans Octadecadienoic acidMeSH, HMDB
Linoleic acid, sodium salt, (e,e)-isomerMeSH, HMDB
Linoleic acid, sodium salt, (Z,Z)-isomerMeSH, HMDB
Acid, 9,12-octadecadienoicMeSH, HMDB
trans,trans-9,12-Octadecadienoic acidMeSH, HMDB
Linoleic acid, (Z,e)-isomerMeSH, HMDB
9,12 Octadecadienoic acidMeSH, HMDB
Linoleic acid, calcium salt, (Z,Z)-isomerMeSH, HMDB
9-trans,12-trans-Octadecadienoic acidMeSH, HMDB
LinoleateMeSH, HMDB, Generator
9E,12E-octadecadienoatehmdb
9E,12E-octadecadienoic acidhmdb
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
Polarizability35.45 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H32O2
IUPAC name(9E,12E)-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-AVQMFFATSA-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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
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
Predicted GC-MSLinoelaidic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0007-9750000000-50d69948d56dd2ba6e42Spectrum
Predicted GC-MSLinoelaidic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-9631000000-cc93c24bbf14d81ae9b6Spectrum
Predicted GC-MSLinoelaidic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0009000000-4dd23c77f8e48c0ab9ecSpectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0009000000-4dd23c77f8e48c0ab9ecSpectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-dd6cf3859995c0ba8be8Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0090000000-fdabfebc98e900a3a52bSpectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0091000000-d8e32f26b102cfd39457Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0090000000-e1aa5a6fc5d53c0d0cb6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-dd6cf3859995c0ba8be8Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-fdabfebc98e900a3a52bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-e1aa5a6fc5d53c0d0cb6Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-fdabfebc98e900a3a52bSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-dd6cf3859995c0ba8be8Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0090000000-e1aa5a6fc5d53c0d0cb6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0190000000-76fe39ad6bbee3f769e7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0239-5690000000-9af1d7ecbc9ccf182d61Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-8930000000-0032f23abecb3b362ff2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-b26f2ec0d32875acf897Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-1090000000-08e28514e79444592bb5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9230000000-d3f27ea65196f222f6cdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-03fd7d53d39127d02766Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-1090000000-e5b6404e73269d5a2528Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9210000000-da81d6d1d7b1e626e905Spectrum
NMRNot Available
ChemSpider ID4445609
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5282457
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06270
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID2217974
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDLinoelaidic acid
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
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).