O1008

Oleic acid

≥99% (GC)

• Synonym(s): 9Z-Octadecenoic acid, cis-Oleic acid, cis-9-Octadecenoic acid, Elainic acid
• Linear Formula: CH₃(CH₂)₇CH=CH(CH₂)₇COOH
• CAS Number: 112-80-1
• Molecular Weight: 282.46
• Beilstein/REAXYS Number: 1726542
• EC Number: 204-007-1
• MDL number: MFCD00064242
• UNSPSC Code: 12352211
• PubChem Substance ID: 24278605
• NACRES: NA.25

Properties

• biological source: plant (Sunflower)
• Quality Level: 200
• vapor pressure: 1 mmHg ( 176 °C)
• assay: ≥99% (GC)
• form: viscous liquid
• color: colorless to very faintly yellow
• refractive index: n20/D 1.459 (lit.)
• bp: 194-195 °C/1.2 mmHg (lit.)
• mp: 13-14 °C (lit.)
• solubility: H₂O: insoluble (practically); alcohol: soluble; benzene: soluble; chloroform: soluble; oil: soluble (fixed and volatile)
• density: 0.89 g/mL at 25 °C (lit.)
• application(s): life science and biopharma; lipidomics
• functional group: oleic acid
• lipid type: unsaturated FAs
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: CCCCCCCC\C=C/CCCCCCCC(O)=O
• InChI: 1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-
• InChI key: ZQPPMHVWECSIRJ-KTKRTIGZSA-N
• Gene Information: human ... PRKCA(5578) , PRKCB(5579) , PRKCD(5580) , PRKCE(5581) , PRKCG(5582) , PRKCH(5583) , PRKCI(5584) , SOAT1(6646) , SOAT2(8435)

Description

General description

Oleic acid (OA), a non-essential fatty acid, is classified as monounsaturated fatty acid (MUFA) richly present in olive oil. Its quantitative removal from the mixtures of triglyceride and partial glycerides has been reported. OA is widely used as a surfactant for the stabilization of magnetic nanoparticles. Monodisperse magnetite nanoparticles (7 and 19nm) coated with OA have been prepared.

Application

Oleic acid has been used:

• to study the effects of fatty acids on gastric cancer (GC)
• to induce lipid droplet formation in cell culture
• as an additive in the magnetorheological fluid preparation.

Oleic acid may be used in the preparation of 10-hydroxy octadecanoic acid and methyl ester of the 10-hydroxy octadecanoic acid.

Biochem/physiol Actions

Oleic acid is known to improve immune function and health. Dietary supplement of this fatty acid contributes to the reduction in cholesterol levels, atherogenesis risk, blood pressure, and host versus graft response. Oleic acid has been proven to benefit autoimmune diseases by exhibiting anti-inflammatory action. It also ameliorates the condition of breast cancer. Oleic acid produces physiological effects such as protein kinase C activation in hepatocytes, uncoupling oxidative phosphorylation, and 2,4-dinitrophenol−stimulated ATPase inhibition. This action can be reversed by adding serum albumin.

Other Notes

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Safety Information

• Storage Class: 10 - Combustible liquids
• wgk_germany: WGK 1
• ppe: Eyeshields, Gloves, type ABEK (EN14387) respirator filter