Record Information
Creation date2015-10-09 22:31:49 UTC
Update date2017-01-19 02:36:32 UTC
FoodComEx IDPC000658
FoodDB RecordFDB012462
Chemical Information
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 (
CAS Number463-40-1
(9,12,15)-Linolenic acidChEBI
(9Z,12Z,15Z)-Octadecatrienoic acidbiospider
(Z,Z,Z)-9,12,15-Octadecatrienoic acidbiospider
α-Linolenic acidbiospider
9-cis,12-cis,15-cis-Octadecatrienoic acidbiospider
9,12,15-Octadecatrienoic acidChEBI
9,12,15-Octadecatrienoic acid, (Z,Z,Z)-biospider
9Z,12Z,15Z-Octadecatrienoic acidbiospider
a-Linolenic aciddb_source
all-cis-9,12,15-Octadecatrienoic acidbiospider
alpha-Linolenic acidbiospider
cis-9,12,15-Octadecatrienoic acidbiospider
cis-Delta(9,12,15)-Octadecatrienoic acidChEBI
cis-δ(9,12,15)-octadecatrienoic acidGenerator
cis,cis,cis-9,12,15-Octadecatrienoic acidbiospider
Industrene 120HMDB
Linolenic acidChEBI
α-linolenic acidGenerator
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-
Average Molecular Weight278.4296
Monoisotopic Molecular Weight278.224580204
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
  • 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
Physico-Chemical Properties - Experimental
Experimental logP6.46SANGSTER (1993)
Experimental Water SolubilityNot Available
Melting PointMp -11.3°DFC
Foods of Origin
FoodContent Range AverageReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 20 mg
Delivery TimeNot Available
Storage Formliquid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez
Commercial Vendors
AKSci M621
Cayman Chemical 90210
Glentham GL9596
MetaSci HMDB0001388
Toronto Research Chemicals L467650
Toronto Research Chemicals HMDB0001388