Record Information
Version1.0
Creation date2010-04-08 22:10:11 UTC
Update date2020-09-17 15:31:13 UTC
Primary IDFDB012462
Secondary Accession Numbers
  • FDB031277
Chemical Information
FooDB Namealpha-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. alpha-Linolenic acid is not synthesized by mammals and therefore is an essential dietary requirement for all mammals. Omega-3 fatty acids get their name based on the location of one of their first double bonds. 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). Although humans and other mammals can synthesize saturated and some monounsaturated fatty acids from carbon groups in carbohydrates and proteins, they lack the enzymes necessary to insert a cis double bond at the n-6 or the n-3 position of a fatty acid. Certain nuts (English walnuts) and vegetable oils (canola, soybean, flaxseed/linseed, olive) are rich in alpha-linolenic acid. Omega-3 fatty acids like alpha-linolenic acid are important structural components of cell membranes. When incorporated into phospholipids, they affect cell membrane properties such as fluidity, flexibility, permeability, and the activity of membrane-bound enzymes. Omega-3 fatty acids can modulate the expression of several genes, including those involved with fatty acid metabolism and inflammation. alpha-Linolenic acid and other omega-3 fatty acids may regulate gene expression by interacting with specific transcription factors, including peroxisome proliferator-activated receptors (PPARs) and liver X receptors (LXRs). alpha-Linolenic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism. Patients with isovaleric acidemia have a defect in leucine catabolism resulting from a deficiency in the enzyme isovaleryl-CoA dehydrogenase. These patients do well on a low protein/low leucine diet but a low protein diet can lead to deficiencies in essential fatty acids, such as alpha-linolenic acid ( https://doi.org/10.1038/ejcn.2016.100).
CAS Number463-40-1
Structure
Thumb
Synonyms
SynonymSource
(9,12,15)-Linolenic acidChEBI
(9Z,12Z,15Z)-Octadecatrienoic acidChEBI
(Z,Z,Z)-9,12,15-Octadecatrienoic acidChEBI
9,12,15-Octadecatrienoic acidChEBI
9-cis,12-cis,15-cis-Octadecatrienoic acidChEBI
ALAChEBI
all-cis-9,12,15-Octadecatrienoic acidChEBI
cis,cis,cis-9,12,15-Octadecatrienoic acidChEBI
cis-Delta(9,12,15)-Octadecatrienoic acidChEBI
Linolenic acidChEBI
LinolenateKegg
alpha-LinolenateKegg
(9,12,15)-LinolenateGenerator
(9Z,12Z,15Z)-OctadecatrienoateGenerator
(Z,Z,Z)-9,12,15-OctadecatrienoateGenerator
9,12,15-OctadecatrienoateGenerator
9-cis,12-cis,15-cis-OctadecatrienoateGenerator
all-cis-9,12,15-OctadecatrienoateGenerator
cis,cis,cis-9,12,15-OctadecatrienoateGenerator
cis-delta(9,12,15)-OctadecatrienoateGenerator
cis-Δ(9,12,15)-octadecatrienoateGenerator
cis-Δ(9,12,15)-octadecatrienoic acidGenerator
a-LinolenateGenerator
a-Linolenic acidGenerator
Α-linolenateGenerator
Α-linolenic acidGenerator
alpha Linolenic acidHMDB
cis-9,12,15-OctadecatrienoateHMDB
cis-9,12,15-Octadecatrienoic acidHMDB
Industrene 120HMDB
FA(18:3(9Z,12Z,15Z))HMDB
FA(18:3n3)HMDB
α-Linolenic acidbiospider
9,12,15-Octadecatrienoic acid, (Z,Z,Z)-biospider
9Z,12Z,15Z-Octadecatrienoatebiospider
9Z,12Z,15Z-Octadecatrienoic acidbiospider
alpha-Linolenic acidbiospider
cis-δ(9,12,15)-octadecatrienoateGenerator
cis-δ(9,12,15)-octadecatrienoic acidGenerator
α-linolenateGenerator
α-linolenic acidGenerator
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC18H30O2
IUPAC name(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
InChI IdentifierInChI=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)/b4-3-,7-6-,10-9-
InChI KeyDTOSIQBPPRVQHS-PDBXOOCHSA-N
Isomeric SMILESCC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O
Average Molecular Weight278.4296
Monoisotopic Molecular Weight278.224580204
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

Industrial application:

Biological role:

Foods

Nuts and legumes:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 77.65%; H 10.86%; O 11.49%DFC
Melting PointMp -11.3°DFC
Boiling PointBp0.05 125°DFC
Experimental Water SolubilityNot Available
Experimental logP6.46SANGSTER (1993)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd204 0.92DFC
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-052f-7900000000-8765cf82603feb1b448fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-004i-9300000000-302519a616eaed5fcc59JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-005c-9800000000-2d44b3c70e2992b9a812JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052f-7900000000-8765cf82603feb1b448fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-9300000000-302519a616eaed5fcc59JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-005c-9800000000-2d44b3c70e2992b9a812JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052f-5900000000-28710ea35f196c595e03JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052e-6950000000-27037263e74c8119ead0JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00ds-6931000000-657fa0cc66a206a36409JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-004i-0190000000-aee97e9ea2c7f0783adfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-05nb-9500000000-fb92aefc701027239359JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0aru-9100000000-a5dddfe6f629d1371facJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-2b7bea03a685454dd135JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0090000000-53ddfaed6ce13c37d957JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0090000000-e5350a66361bc63d1071JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0090000000-5731aa5e301022c06813JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0091010000-6922411e48d747e592b5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-001i-0090000000-a18b573ad888d048efa6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-2b7bea03a685454dd135JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-e5350a66361bc63d1071JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-5731aa5e301022c06813JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-004i-0090000000-1d391027db3704d71cb9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-00lr-9210000000-41acd8a55f52afec6d79JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-014i-9000000000-a976b4a80a07eb2c4641JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0090000000-ae1f482177d0e208165eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00o0-5690000000-20804c8382f14ff0ccf4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-8930000000-9d5e342b1351adc71c20JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-4d3e8d1180800a7b4ed5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-1090000000-67ab14c068a142dd3c30JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9230000000-403c610d63380e63109aJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID4444437
ChEMBL IDCHEMBL8739
KEGG Compound IDC06427
Pubchem Compound ID5280934
Pubchem Substance IDNot Available
ChEBI ID27432
Phenol-Explorer IDNot Available
DrugBank IDDB00132
HMDB IDHMDB01388
CRC / DFC (Dictionary of Food Compounds) IDCPM16-L:HHB80-W
EAFUS IDNot Available
Dr. Duke IDCIS-LINOLEIC-ACID|ALPHA-LINOLENIC-ACID|LINOLENIC-ACID
BIGG ID48237
KNApSAcK IDC00007247
HET IDLNL
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1045911
SuperScent IDNot Available
Wikipedia IDAlpha-Linolenic_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 / Bioactivities
DescriptorIDDefinitionReference
5alpha-reductase inhibitor50781 An EC 1.3.1.* (oxidoreductase acting on CH-CH group of donor, NAD(+) or NADP(+) as acceptor) inhibitor that interferes with the action of of 3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+)), EC 1.3.1.22, the enzyme which converts testosterone (CHEBI:17347) into the more potent androgen 5alpha-dihydrotestosterone.DUKE
anti aggregantDUKE
anti hypertensive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti leukotriene-D435222 A substance that diminishes the rate of a chemical reaction.DUKE
anti menorrhagic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti metastatic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti prostatiticDUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
hypotensiveDUKE
immunostimulant50847 A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.DUKE
lymphocytogenicDUKE
propecicDUKE
prostaglandin synthesis inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
Enzymes
NameGene NameUniProt ID
Bile acid-CoA:amino acid N-acyltransferaseBAATQ14032
Cytosolic acyl coenzyme A thioester hydrolaseACOT7O00154
Acyl-coenzyme A thioesterase 2, mitochondrialACOT2P49753
Acyl-coenzyme A thioesterase 4ACOT4Q8N9L9
Acyl-coenzyme A thioesterase 8ACOT8O14734
Acyl-coenzyme A thioesterase 1ACOT1Q86TX2
Elongation of very long chain fatty acids protein 4ELOVL4Q9GZR5
Pathways
NameSMPDB LinkKEGG Link
Alpha Linolenic Acid and Linoleic Acid MetabolismSMP00018 map00592
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
faint
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fatty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.