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Showing Compound alpha-Linoleic acid (FDB006287)

Record Information
Version1.0
Creation date2010-04-08 22:07:04 UTC
Update date2020-09-17 15:42:28 UTC
Primary IDFDB006287
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namealpha-Linoleic acid
DescriptionLinoleic acid is a doubly unsaturated fatty acid or polyunsaturated fatty acid (PUFA). It is also known as an omega-6 fatty acid, occurring widely in plant glycosides. In linoleic acid 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 a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Linoleic acid is a colorless or white oil with a faint, fatty odor. 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 the lipids of cell membranes. Altered levels of linoleic acid have been found to be associated with isovaleric acidemia, which is an inborn error of metabolism. Conjugated linoleic acids have been studied for their beneficial effects in the prevention and treatment of many diseases, including obesity, cancer, diabetes, and cardiovascular diseases (PMID: 27636835). Linoleic acid can be found in all living organisms, ranging from bacteria to humans, although it cannot be synthesized by mammals. In rats, a diet deficient in linoleate (the salt form of the acid) has been shown to cause mild skin scaling, hair loss, (PMID: 9144095) and poor wound healing (PMID: 10498749). Linoleic acid is abundant in many nuts, fatty seeds (flax seeds, hemp seeds, poppy seeds, sesame seeds, etc.) and their derived vegetable oils; comprising over half (by weight) of poppy seed, safflower, sunflower, corn, and soybean oils. Linoleic acid is used in making quick-drying oils, which are useful in oil paints and varnishes. Linoleic acid has become increasingly popular in the beauty products industry because of its beneficial properties on the skin. A number of reports have identified linoleic acid's anti-inflammatory, acne reductive, skin-lightening and moisture retentive properties when applied topically on the skin (PMID: 9692305; PMID: 9749992).
CAS Number60-33-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
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
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
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 IDALPHA-LINOLEIC-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
Processing...
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— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).