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Oleic acid

Oleic acid
Oleic acid
Oleic-acid-3D-vdW.png
Names
Preferred IUPAC name
(9Z)-Octadec-9-enoic acid
Other names
Oleic acid
(9Z)-Octadecenoic acid
(Z)-Octadec-9-enoic acid
cis-9-Octadecenoic acid
cis9-Octadecenoic acid
18:1 cis-9
Identifiers
112-80-1 YesY
3D model (Jmol) Interactive image
ChEMBL ChEMBL8659 N
ChemSpider 393217 N
ECHA InfoCard 100.003.643
1054
Properties
C18H34O2
Molar mass 282.47 g·mol−1
Appearance Pale yellow or brownish yellow oily liquid with lard-like odor
Density 0.895 g/mL
Melting point 13 to 14 °C (55 to 57 °F; 286 to 287 K)
Boiling point 360 °C (680 °F; 633 K)
Insoluble
Solubility in Ethanol Soluble
-208.5·10−6 cm3/mol
Hazards
Safety data sheet JT Baker
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g., sodium chloride Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Related compounds
Related compounds
Elaidic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

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. In chemical terms, oleic acid is classified as a monounsaturated omega-9 fatty acid, abbreviated with a lipid number of 18:1 cis-9. It has the formula CH3(CH2)7CH=CH(CH2)7COOH. The term "oleic" means related to, or derived from, olive oil which is predominantly composed of oleic acid. The corresponding stereoisomer trans-9-Octadecenoic acid is called Elaidic acid. These isomers have distinct physical properties and biochemical properties. Elaidic acid, the most abundant trans fatty acid in diet, appears to have an adverse effect on health.

Fatty acids (or their salts) do not often occur as such in biological systems. Instead fatty acids like oleic acid occur as their esters, commonly triglycerides, which are the greasy materials in many natural oils. Fatty acids can be obtained via the process of saponification.

Triglycerides of oleic acid compose the majority of olive oil, although there may be less than 2.0% as free acid in virgin olive oil, with higher concentrations making the olive oil inedible. It also makes up 59-75% of pecan oil, 61% of canola oil, 36-67% of peanut oil, 60% of macadamia oil, 20-85% of sunflower oil (the latter in the high oleic variant), 15-20% of grape seed oil, sea buckthorn oil, and sesame oil, and 14% of poppyseed oil. It is abundantly present in many animal fats, constituting 37 to 56% of chicken and turkey fat and 44 to 47% of lard.


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