Record Information
Version2.0
Creation Date2012-05-31 13:51:24 -0600
Update Date2015-10-02 02:25:49 -0600
Secondary Accession Numbers
  • ECMDB01388
Identification
Name:alpha-Linolenic acid
DescriptionAlpha-linolenic acid (ALA) is a polyunsaturated fatty acid (PUFA). It is a member of the group of essential fatty acids called omega-3 fatty acids. Omega-3 fatty acids get their name based on the location of one of their first double bond. In all omega-3 fatty acids, the first double bond is located between the third and fourth carbon atom counting from the methyl end of the fatty acid (n-3). Omega-3 fatty acids can modulate the expression of a number of genes, including those involved with fatty acid metabolism. Alpha linolenic acid and other omega 3 fatty acids may regulate gene expression by interacting with specific transcription factors. ALA is an intermediate in alpha-Linolenic acid metabolism and biosynthesis of unsaturated fatty acids pathway in E. coli (KEGG compound: C06427).
Structure
Thumb
Synonyms:
  • (9,12,15)-linolenate
  • (9,12,15)-linolenic acid
  • (9E,12E,15E)-9,12,15-Octadecatrienoate
  • (9E,12E,15E)-9,12,15-Octadecatrienoic acid
  • (9Z,12Z,15Z)-Octadecatrienoate
  • (9Z,12Z,15Z)-Octadecatrienoic acid
  • (Z,Z,Z)-9,12,15-Octadecatrienoate
  • (Z,Z,Z)-9,12,15-Octadecatrienoic acid
  • 9,12,15-Octadecatrienoate
  • 9,12,15-Octadecatrienoic acid
  • 9-cis,12-cis,15-cis-Octadecatrienoate
  • 9-cis,12-cis,15-cis-Octadecatrienoic acid
  • 9Z,12Z,15Z-octadecatrienoate
  • 9Z,12Z,15Z-octadecatrienoic acid
  • A-Linolenate
  • A-Linolenic acid
  • All-cis-9,12,15-Octadecatrienoate
  • All-cis-9,12,15-Octadecatrienoic acid
  • alpha-Linolenate
  • Alpha-Linolenic acid
  • Cis,cis,cis-9,12,15-Octadecatrienoate
  • Cis,cis,cis-9,12,15-Octadecatrienoic acid
  • Cis-9,12,15-Octadecatrienoate
  • Cis-9,12,15-Octadecatrienoic acid
  • Industrene 120
  • Linolenate
  • Linolenic acid
  • α-Linolenate
  • α-Linolenic acid
Chemical Formula:C18H30O2
Weight:Average: 278.4296
Monoisotopic: 278.224580204
InChI Key:DTOSIQBPPRVQHS-UHFFFAOYSA-N
InChI:InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)
CAS number:463-40-1
IUPAC Name:(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
Traditional IUPAC Name:α linolenic acid
SMILES:CCC=CCC=CCC=CCCCCCCCC(O)=O
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
Physical Properties
State:Liquid
Charge:-1
Melting point:-16.5 °C
Experimental Properties:
PropertyValueSource
LogP:6.46 [SANGSTER (1993)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00027 g/LALOGPS
logP6.62ALOGPS
logP6.06ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity89.64 m³·mol⁻¹ChemAxon
Polarizability34.98 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
  • Biosynthesis of unsaturated fatty acids ec01040
  • alpha-Linolenic acid metabolism ec00592
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-052f-7900000000-8765cf82603feb1b448fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-004i-9300000000-302519a616eaed5fcc59View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-005c-9800000000-2d44b3c70e2992b9a812View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052f-7900000000-8765cf82603feb1b448fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-9300000000-302519a616eaed5fcc59View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-005c-9800000000-2d44b3c70e2992b9a812View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052f-5900000000-28710ea35f196c595e03View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052e-6950000000-27037263e74c8119ead0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00ds-6931000000-657fa0cc66a206a36409View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-004i-0190000000-aee97e9ea2c7f0783adfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-05nb-9500000000-fb92aefc701027239359View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0aru-9100000000-a5dddfe6f629d1371facView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-2b7bea03a685454dd135View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0090000000-53ddfaed6ce13c37d957View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0090000000-e5350a66361bc63d1071View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0090000000-5731aa5e301022c06813View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0091010000-6922411e48d747e592b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-001i-0090000000-a18b573ad888d048efa6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-2b7bea03a685454dd135View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-e5350a66361bc63d1071View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-5731aa5e301022c06813View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-004i-0090000000-1d391027db3704d71cb9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-00lr-9210000000-41acd8a55f52afec6d79View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-014i-9000000000-a976b4a80a07eb2c4641View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-497eddf5d738a45f83fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-0c00ca98901526cb2e26View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-004i-1090000000-35ffce9343fe0d15ea0dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-004i-0090000000-373584fbab950d6676ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0090000000-ae1f482177d0e208165eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00o0-5690000000-20804c8382f14ff0ccf4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-8930000000-9d5e342b1351adc71c20View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-4d3e8d1180800a7b4ed5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-1090000000-67ab14c068a142dd3c30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9230000000-403c610d63380e63109aView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:Li, Guihua; Qian, Xiangming; Jiang, Yanchao; Ma, Shushi. Preparation of a-linolenic acid from linseed oil. Zhengzhou Gongcheng Xueyuan Xuebao (2004), 25(3), 13-15.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID27432
HMDB IDHMDB01388
Pubchem Compound ID860
Kegg IDC06427
ChemSpider ID4445949
WikipediaLinolenic acid
BioCyc IDLINOLENIC_ACID
EcoCyc IDLINOLENIC_ACID

Enzymes

General function:
Involved in phospholipase activity
Specific function:
Has broad substrate specificity including hydrolysis of phosphatidylcholine with phospholipase A2 (EC 3.1.1.4) and phospholipase A1 (EC 3.1.1.32) activities. Strong expression leads to outer membrane breakdown and cell death; is dormant in normal growing cells. Required for efficient secretion of bacteriocins
Gene Name:
pldA
Uniprot ID:
P0A921
Molecular weight:
33163
Reactions
Phosphatidylcholine + H(2)O = 2-acylglycerophosphocholine + a carboxylate.
Phosphatidylcholine + H(2)O = 1-acylglycerophosphocholine + a carboxylate.