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.
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.