Oleic acid

Oleic acid

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 cis-Δ9-Octadecenoic acid 18:1 cis-9
Identifiers
CAS Number	112-80-1 Y
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL8659 N
ChemSpider	393217 N
ECHA InfoCard	100.003.643
IUPHAR/BPS	1054
InChI 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- N Key: ZQPPMHVWECSIRJ-KTKRTIGZSA-N N InChI=1/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- Key: ZQPPMHVWECSIRJ-KTKRTIGZBB
SMILES CCCCCCCC\C=C/CCCCCCCC(O)=O
Properties
Chemical formula	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)
Solubility in water	Insoluble
Solubility in Ethanol	Soluble
Magnetic susceptibility (χ)	-208.5·10−6 cm3/mol
Hazards
Safety data sheet	JT Baker
NFPA 704	1 0 0
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 YN ?)
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.