oleic acid

Also 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

OverviewAI-generated

Oleic acid, also identified by the IUPAC name (Z)-octadec-9-enoic acid, is a chemical compound with the formula C₁₈H₃₄O₂. It has a melting point of 17 and a boiling point of 360. The substance possesses a mass of 282.256 and a dynamic viscosity of 25.6. Its structure is represented by the canonical SMILES string CCCCCCCCC=CCCCCCCCC(=O)O and the isomeric SMILES string CCCCCCCC\C=C/CCCCCCCC(O)=O.

According to PubChem data, the compound has a weight of 282.5 and an xlogp value of 6.5. It features a topological polar surface area of 37.3, with one hydrogen bond donor and two hydrogen bond acceptors. The molecule carries a charge of 0. In the scientific literature, oleic acid is the subject of 29,948 PubMed entries. Additionally, the compound is referenced by 580 other encyclopedia articles.

Synthesized by Vinony from 22 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still 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 Å²
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

~6 min read

Encyclopedic overview

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

Excerpted from Wikipedia’s “oleic acid” article, available under the CC BY-SA 4.0 licence.