Structure via PubChem · Public domain (PubChem)
linoleic acid
Sign in to saveAlso known as linolic acid, telfairic acid, cis,cis-linoleic acid, 9Z,12Z-octadecadienoic acid, LA, all-cis-9,12-octadecadienoic acid, C18:2, n-6,9 all-cis, cis,cis-9,12-octadecadienoic acid
chemical compound and essential nutrient
OverviewAI-generated
Linoleic acid is a chemical compound with the formula C₁₈H₃₂O₂. Its IUPAC name is (9Z,12Z)-octadeca-9,12-dienoic acid. The substance has a mass of 280.24 and a weight of 280.4. It melts at -5 and boils at 365.2.
The compound has an xlogp of 6.8 and a topological polar surface area of 37.3. It contains one hydrogen bond donor and two hydrogen bond acceptors, with a charge of 0. The canonical SMILES representation is CCCCCC=CCC=CCCCCCCCC(=O)O, while the isomeric SMILES is CCCCC/C=C\C/C=C\CCCCCCCC(=O)O.
Linoleic acid is referenced by 797 other encyclopedia articles. A PubMed query for the term yields a count of 30386.
Synthesized by Vinony from 20 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.
In the Vinony graph
Vinony's link graph records 797 inbound references to linoleic acid, and connects out to Prunus amygdalus, fatty acid and biodiesel.
Vinony files it under 5α-Reductase inhibitors, Alkenoic acids and Aromatase inhibitors.
Vinony links it to 44 Wikipedia language editions.
Chemical data
- Formula
- C18H32O2
- Molecular weight
- 280.4 g/mol
- IUPAC name
- (9Z,12Z)-octadeca-9,12-dienoic acid
- SMILES
- CCCCC/C=C\C/C=C\CCCCCCCC(=O)O
- InChIKey
- OYHQOLUKZRVURQ-HZJYTTRNSA-N
- XLogP
- 6.8
- Polar surface area
- 37.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- neoplasm, obesity, breast cancer, asthma
via ChEMBL · EBI
Research
30,386 papers- Linoleic acid.Advances in nutrition (Bethesda, Md.) · 2013
- Linoleic acid and the pathogenesis of obesity.Prostaglandins & other lipid mediators · 2016
- Linoleic acid and breast cancer risk: a meta-analysis.Public health nutrition · 2016
- Conjugated linoleic acid metabolism.Current opinion in lipidology · 2002
- Conjugated linoleic acid.Animal health research reviews · 2000
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 280.24
Show 9 more facts
- found in taxon
- Habenaria intermedia
- canonical SMILES
- CCCCCC=CCC=CCCCCCCCC(=O)O
- Commons category
- Linoleic acid
- isomeric SMILES
- CCCCC/C=C\C/C=C\CCCCCCCC(=O)O
- chemical formula
- C₁₈H₃₂O₂
- subject has role
- 5-alpha-reductase inhibitors
- melting point
- -5
- medical condition treated
- nutrition disorder
- boiling point
- 365.2
Sources (6)
via Wikidata · CC0
~8 min read
Encyclopedic overview
Linoleic acid (LA) is an organic compound with the formula CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH. Both alkene groups (−CH=CH−) are cis. It is a fatty acid sometimes denoted 18:2 (n−6) or 18:2 cis-9,12. A linoleate is a salt or ester of this acid.
Linoleic acid is a polyunsaturated, omega−6 fatty acid. It is a colorless liquid that is virtually insoluble in water but soluble in many organic solvents. It typically occurs in nature as a triglyceride (ester of glycerin) rather than as a free fatty acid. It is one of two essential fatty acids for humans, who must obtain it through their diet, and the most essential, because the body uses it as a base to make the others.
Excerpted from Wikipedia’s “linoleic acid” article, available under the CC BY-SA 4.0 licence.