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Linoleic acid
Names
IUPAC name
(9Z,12Z)-9,12-Octadecadienoic acid
Other names
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • 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- checkY
    Key: OYHQOLUKZRVURQ-HZJYTTRNSA-N checkY
  • 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
  • CCCCC/C=C\C/C=C\CCCCCCCC(=O)O
Properties
C18H32O2
Molar mass 280.452 g·mol−1
Appearance Colorless oil
Density 0.9 g/cm3[2]
Melting point −5 °C (23 °F)[3]
−12 °C (10 °F)[2]
Boiling point 230 °C (446 °F) at 21 mbar[3]
230 °C (446 °F) at 16 mmHg[2]
0.139 mg/L[3]
Vapor pressure 16 Torr at 229 °C[citation needed]
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 112 °C (234 °F)[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Tracking categories (test):

Linoleic acid (LA) is an unsaturated 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. Chemically, linoleic acid is a carboxylic acid with an 18-carbon chain and two cis double bonds; the first double bond is located at the sixth carbon from the methyl end.[4]

Linoleic acid belongs to one of the two families of essential fatty acids. The body cannot synthesize linoleic acid from other food components.[5]

The word "linoleic" comes 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.

Some medical research suggests that excessive levels of certain omega−6 fatty acids relative to certain omega-3 fatty acids, but likely in conjunction with exogenous toxins, may have negative health effects.[citation needed]

  1. ^ [author missing] (2015 [last update]). "Google Translate Blog: Translating Wikipedia". googletranslate.blogspot.in. Retrieved May 28, 2015. {{cite web}}: |last= has generic name (help); Check date values in: |date= (help)CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link)
  2. ^ a b c The Merck Index, 11th Edition, 5382
  3. ^ a b c d Record of CAS RN 60-33-3 in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  4. ^ David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia of Industrial Chemistry, 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_245.pub2
  5. ^ Burr, G.O., Burr, M.M. and Miller, E. (1930). "On the nature and role of the fatty acids essential in nutrition" (PDF). J. Biol. Chem. 86 (587): 1–9. doi:10.1016/S0021-9258(20)78929-5.{{cite journal}}: CS1 maint: multiple names: authors list (link)