File:Oleic-acid-skeletal.svg · Wikimedia Commons · See Wikimedia Commons
oleic acid
Sign in to saveAlso known as cis-9-octadecenoic acid, cis-Delta(9)-octadecenoic acid, 18:1delta9cis, 18:1 n-9, C18:1 n-9, oleinic acid, 9-octadecenoic acid (9Z)-, 9-octadecenoic acid
monounsaturated omega-9 fatty acid, abbreviated with a lipid number of 18:1 cis-9
Oleic acid is a type of fat found in foods like olive oil and avocados that has a chemical structure with one double bond, making it a monounsaturated fat. It's considered one of the more beneficial dietary fats and is often associated with the health benefits of Mediterranean diets.
AI-generated from the Wikipedia summary — may contain errors.
Chemical data
- Formula
- C18H34O2
- Molecular weight
- 282.5 g/mol
- IUPAC name
- (Z)-octadec-9-enoic acid
- SMILES
- CCCCCCCC/C=C\CCCCCCCC(=O)O
- InChIKey
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N
- XLogP
- 6.5
- Polar surface area
- 37.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
29,948 papers- Oleic acid in the modulation of oocyte and preimplantation embryo development.ReviewZygote (Cambridge, England) · 2018Fayezi S, Leroy JLMR, Ghaffari Novin M et al.DOI: 10.1017/S0967199417000582
- Oleic acid blocks the calcium-activated chloride channel TMEM16A/ANO1.Biochimica et biophysica acta. Molecular and cell biology of lipids · 2022Leon-Aparicio D, Sánchez-Solano A, Arreola J et al.DOI: 10.1016/j.bbalip.2022.159134
- Producing high-oleic acid beef and the impact of ground beef consumption on risk factors for cardiovascular disease: A review.ReviewMeat science · 2020Smith SB, Lunt DK, Smith DR et al.DOI: 10.1016/j.meatsci.2020.108076
- Oleic acid stimulates monoamine efflux through PPAR-α: Differential effects in diet-induced obesity.Life sciences · 2020Jagannathan L, Socks E, Balasubramanian P et al.DOI: 10.1016/j.lfs.2020.117867
- The mechanism of oleic acid inhibiting platelet activation stimulated by collagen.Cell communication and signaling : CCS · 2023Zhou X, Zhou X, Zhu R et al.DOI: 10.1186/s12964-023-01276-0
- Oleic acid triggers burial behavior in a termite population through an odorant binding protein.Insect biochemistry and molecular biology · 2024Li H, Liu J, Wang Q et al.DOI: 10.1016/j.ibmb.2024.104090
- Astrocyte-synthesized oleic acid behaves as a neurotrophic factor for neurons.ReviewJournal of physiology, Paris · 2002Medina JM, Tabernero ADOI: 10.1016/s0928-4257(02)00015-3
- Genetic and metabolic engineering of oleic acid synthesis pathways in oil palm: Challenges and future prospects.ReviewPlant physiology and biochemistry : PPB · 2025Imran M, Huangying S, Hongshuo Z et al.DOI: 10.1016/j.plaphy.2025.110288
via PubMed
Wikidata facts
- Mass
- 282.256
Show 8 more facts
- Commons category
- Oleic acid
- melting point
- 13.4
- boiling point
- 360
- chemical formula
- C₁₈H₃₄O₂
- canonical SMILES
- CCCCCCCCC=CCCCCCCCC(=O)O
- dynamic viscosity
- 25.6
- isomeric SMILES
- CCCCCCCC\C=C/CCCCCCCC(O)=O
- NCI Thesaurus ID
- C68405
Sources (6)
via Wikidata · CC0
~6 min read
Article
Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish due to the presence of impurities. In chemical terms, oleic acid is classified as a monounsaturated omega-9 fatty acid, abbreviated with a lipid number of 18:1 cis-9, and a main product of Δ9-desaturase. It has the formula CH3−(CH2)7−CH=CH−(CH2)7−COOH. The name derives from the Latin word oleum, which means oil. It is the most common fatty acid in nature. The salts and esters of oleic acid are called oleates. It is a common component of oils, and thus occurs in many types of food, as well as in soap.
Occurrence