Structure via PubChem · Public domain (PubChem)
alpha-linolenic acid
Sign in to saveAlso known as α-LA, linolenate, 9-cis,12-cis,15-cis-octadecatrienoic acid, cis-Delta(9,12,15)-octadecatrienoic acid, (9,12,15)-linolenic acid, all-cis-9,12,15-octadecatrienoic acid, cis,cis,cis-9,12,15-octadecatrienoic acid, (Z,Z,Z)-9,12,15-octadecatrienoic acid
omega-3 polyunsaturated fatty acid
OverviewAI-generated
Alpha-linolenic acid is a chemical compound with the formula C₁₈H₃₀O₂. Its IUPAC name is (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid. The substance has a molecular weight of 278.4 and a mass of 278.225. It exhibits a melting point of -113.
Chemical properties include an xlogp value of 5.9 and a topological polar surface area of 37.3. The molecule contains one hydrogen bond donor and two hydrogen bond acceptors, with a charge of 0. It is referenced by 414 other encyclopedia articles.
Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Chemical data
- Formula
- C18H30O2
- Molecular weight
- 278.4 g/mol
- IUPAC name
- (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
- SMILES
- CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)O
- InChIKey
- DTOSIQBPPRVQHS-PDBXOOCHSA-N
- XLogP
- 5.9
- Polar surface area
- 37.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
9,712 papers- The review of alpha-linolenic acid: Sources, metabolism, and pharmacology.Phytotherapy research : PTR · 2022
- Alpha-Linolenic Acid and Cardiovascular Events: A Narrative Review.International journal of molecular sciences · 2023
- The Role of Alpha-Linolenic Acid and Other Polyunsaturated Fatty Acids in Mental Health: A Narrative Review.International journal of molecular sciences · 2024
- The Role of α-Linolenic Acid and Its Oxylipins in Human Cardiovascular Diseases.International journal of molecular sciences · 2023
- α-linolenic acid interconversion is sufficient as a source of longer chain ω-3 polyunsaturated fatty acids in humans: An opinion.Lipids · 2022
via PubMed
Wikidata facts
- Subclass of
- essential fatty acid
- Has part
- oxygen
- Named after
- Linum
- Mass
- 278.225
- Has use
- medication
Show 9 more facts
- found in taxon
- Epilobium dodonaei
- chemical formula
- C₁₈H₃₀O₂
- canonical SMILES
- CCC=CCC=CCC=CCCCCCCCC(=O)O
- isomeric SMILES
- CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)O
- medical condition treated
- nutrition disorder
- melting point
- -113
- Commons category
- Alpha-Linolenic acid
- has characteristic
- bitterness
- subject has role
- primary metabolite
Sources (7)
via Wikidata · CC0
~6 min read
Encyclopedic overview
α-Linolenic acid, also known as alpha-linolenic acid (ALA) (from Greek alpha denoting "first" and linon meaning flax), is an n−3, or omega-3, essential fatty acid. ALA is found in many seeds and oils, including flaxseed, walnuts, chia, hemp, and many common vegetable oils.
In terms of its structure, it is named all-cis-9,12,15-octadecatrienoic acid. In physiological literature, it is listed by its lipid number, 18:3 (n−3). It is a carboxylic acid with an 18-carbon chain and three cis double bonds. The first double bond is located at the third carbon from the methyl end of the fatty acid chain, known as the n end. Thus, α-linolenic acid is a polyunsaturated n−3 (omega-3) fatty acid. It is a regioisomer of gamma-linolenic acid (GLA), an 18:3 (n−6) fatty acid (i.e., a polyunsaturated omega-6 fatty acid with three double bonds).
Excerpted from Wikipedia’s “alpha-linolenic acid” article, available under the CC BY-SA 4.0 licence.