FComEx: alpha-Linolenic acid (PC000658)

Record Information

Version

1.0

Creation date

2015-10-09 22:31:49 UTC

Update date

2017-01-19 02:36:32 UTC

FoodComEx ID

PC000658

FoodDB Record

FDB012462

Chemical Information

Name

alpha-Linolenic acid

Description

alpha-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 Number

463-40-1

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
(9,12,15)-Linolenate	Generator
(9,12,15)-Linolenic acid	ChEBI
(9Z,12Z,15Z)-Octadecatrienoate	biospider
(9Z,12Z,15Z)-Octadecatrienoic acid	biospider
(Z,Z,Z)-9,12,15-Octadecatrienoate	biospider
(Z,Z,Z)-9,12,15-Octadecatrienoic acid	biospider
α-Linolenic acid	biospider
9-cis,12-cis,15-cis-Octadecatrienoate	biospider
9-cis,12-cis,15-cis-Octadecatrienoic acid	biospider
9,12,15-Octadecatrienoate	Generator
9,12,15-Octadecatrienoic acid	ChEBI
9,12,15-Octadecatrienoic acid, (Z,Z,Z)-	biospider
9Z,12Z,15Z-Octadecatrienoate	biospider
9Z,12Z,15Z-Octadecatrienoic acid	biospider
a-Linolenate	biospider
a-Linolenic acid	db_source
all-cis-9,12,15-Octadecatrienoate	biospider
all-cis-9,12,15-Octadecatrienoic acid	biospider
alpha-Linolenate	biospider
alpha-Linolenic acid	biospider
cis-9,12,15-Octadecatrienoate	biospider
cis-9,12,15-Octadecatrienoic acid	biospider
cis-delta(9,12,15)-Octadecatrienoate	Generator
cis-Delta(9,12,15)-Octadecatrienoic acid	ChEBI
cis-δ(9,12,15)-octadecatrienoate	Generator
cis-δ(9,12,15)-octadecatrienoic acid	Generator
cis,cis,cis-9,12,15-Octadecatrienoate	biospider
cis,cis,cis-9,12,15-Octadecatrienoic acid	biospider
Industrene 120	HMDB
Linolenate	Generator
Linolenic acid	ChEBI
α-linolenate	Generator
α-linolenic acid	Generator

Chemical Formula

C18H30O2

IUPAC name

(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid

InChI Identifier

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)/b4-3-,7-6-,10-9-

InChI Key

DTOSIQBPPRVQHS-PDBXOOCHSA-N

Isomeric SMILES

CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O

Average Molecular Weight

278.4296

Monoisotopic Molecular Weight

278.224580204

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents