Linoelaidic acid (CHEM022815)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:54:55 UTC
Update Date2016-11-09 01:17:35 UTC
Accession NumberCHEM022815
Identification
Common NameLinoelaidic acid
ClassSmall Molecule
DescriptionAn octadecadienoic acid containing two E (trans) double bonds at positions 9 and 12.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC18H32O2
Average Molecular Mass280.446 g/mol
Monoisotopic Mass280.240 g/mol
CAS Registry Number506-21-8
IUPAC Name(9E,12E)-octadeca-9,12-dienoic acid
Traditional Namelinoelaidic acid
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-AVQMFFATSA-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
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
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
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0009000000-4dd23c77f8e48c0ab9ecSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0009000000-4dd23c77f8e48c0ab9ecSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-dd6cf3859995c0ba8be8Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0090000000-fdabfebc98e900a3a52bSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0091000000-d8e32f26b102cfd39457Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0090000000-e1aa5a6fc5d53c0d0cb6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-dd6cf3859995c0ba8be8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-fdabfebc98e900a3a52bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-e1aa5a6fc5d53c0d0cb6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-fdabfebc98e900a3a52bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-dd6cf3859995c0ba8be8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0090000000-e1aa5a6fc5d53c0d0cb6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0190000000-76fe39ad6bbee3f769e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0239-5690000000-9af1d7ecbc9ccf182d61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-8930000000-0032f23abecb3b362ff2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-b26f2ec0d32875acf897Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-1090000000-08e28514e79444592bb5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9230000000-d3f27ea65196f222f6cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-03fd7d53d39127d02766Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-1090000000-e5b6404e73269d5a2528Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9210000000-da81d6d1d7b1e626e905Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0006270
FooDB IDFDB023868
Phenol Explorer IDNot Available
KNApSAcK IDC00036669
BiGG ID2217974
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLinoelaidic_acid
Chemspider ID4445609
ChEBI ID75108
PubChem Compound ID5282457
Kegg Compound IDNot Available
YMDB IDYMDB00884
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1943087
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22198657
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22216328
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23065354
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23945414
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=6818563
7. Gunstone, Frank D.; Lie Ken Jie, M. Fatty acids. 24. Synthesis of ten octadecadiynoic acids and of the related cis,cis- and trans,trans-octadecadienoic acids. Chemistry and Physics of Lipids (1970), 4(1), 1-14.
8. Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026.
9. Gunstone, Frank D.; Lie Ken Jie, M. Fatty acids. 24. Synthesis of ten octadecadiynoic acids and of the related cis,cis- and trans,trans-octadecadienoic acids. Chemistry and Physics of Lipids (1970), 4(1), 1-14.
10. MacDonald HB: Conjugated linoleic acid and disease prevention: a review of current knowledge. J Am Coll Nutr. 2000 Apr;19(2 Suppl):111S-118S.