Linoleic acid

Linoleic acid
Names



IUPAC name (9Z,12Z)-9,12-Octadecadienoic acid
Other names C18:2 (Lipid numbers)
Identifiers
CAS Number	60-33-3^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17351^Y
ChEMBL	ChEMBL267476^Y
ChemSpider	4444105^Y
ECHA InfoCard	100.000.428
IUPHAR/BPS	1052
KEGG	C01595^Y
UNII	9KJL21T0QJ^Y
InChI InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-^Y Key: OYHQOLUKZRVURQ-HZJYTTRNSA-N^Y InChI=1/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9- Key: OYHQOLUKZRVURQ-HZJYTTRNBX
SMILES CCCCC/C=C\C/C=C\CCCCCCCC(=O)O
Properties
Chemical formula	C₁₈H₃₂O₂
Molar mass	280.45 g·mol⁻¹
Appearance	Colorless oil
Density	0.9 g/cm³
Melting point	−5 °C (23 °F) −12 °C (10 °F)
Boiling point	230 °C (446 °F) at 21 mbar 230 °C (446 °F) at 16 mmHg
Solubility in water	0.139 mg/L
Vapor pressure	16 Torr at 229 °C
Hazards
NFPA 704	1 2 0
Flash point	112 °C (234 °F)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y (what is ^YN ?)
Infobox references

Linoleic acid (LA) is a polyunsaturated omega-6 fatty acid. It is a colorless liquid at room temperature. In physiological literature, it has a lipid number of 18:2 cis,cis-9,12. Linoleic acid is a carboxylic acid with an 18-carbon chain and two cis double bonds; with the first double bond located at the sixth carbon from the methyl end.

Linoleic acid belongs to one of the two families of essential fatty acids, which means that the human body cannot synthesize it from other food components.

The word "linoleic" derived from the Greek word linon (flax). Oleic means "of, relating to, or derived from oil of olive" or "of or relating to oleic acid" because saturating the omega-6 double bond produces oleic acid.

LA is a polyunsaturated fatty acid used in the biosynthesis of arachidonic acid (AA) and thus some prostaglandins, leukotrienes (LTA, LTB, LTC), and thromboxane (TXA). It is found in the lipids of cell membranes. It is abundant in many nuts, fatty seeds (flax seeds, hemp seeds, poppy seeds, sesame seeds, etc.) and their derived vegetable oils; comprising over half (by weight) of poppy seed, safflower, sunflower, corn, and soybean oils.

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