Back حمض اللينولييك Arabic اسید لینولئیک AZB Лінолевая кіслата Byelorussian Àcid linoleic Catalan Kyselina linolová Czech Linolsyre Danish Linolsäure German Λινελαϊκό οξύ Greek Linoleata acido Esperanto Ácido linoleico Spanish

Linoleic acid

Not to be confused with linolenic acid, alpha-linolenic acid, lipoic acid, or linolelaidic acid.

Linoleic acid
Names
Preferred IUPAC name
(9Z,12Z)-Octadeca-9,12-dienoic acid
Other names
cis,cis-9,12-Octadecadienoic acid
C18:2 (Lipid numbers)
Identifiers
3D model (JSmol)
3DMet
1727101
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.428 Edit this at Wikidata
EC Number
  • 200-470-9
57557
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[1]
Melting point −12 °C (10 °F)[1]
−6.9 °C (19.6 °F)[2]
−5 °C (23 °F)[3]
Boiling point 229 °C (444 °F) at 16 mmHg[2]
230 °C (446 °F) at 21 mbar[3]
230 °C (446 °F) at 16 mmHg[1]
0.139 mg/L[3]
Vapor pressure 16 Torr at 229 °C[citation needed]
Acidity (pKa) 4.77 at 25°C[4]
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).
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Linoleic acid (LA) is an organic compound with the formula HOOC(CH2)7CH=CHCH2CH=CH(CH2)4CH3. Both alkene groups (−CH=CH−) are cis. It is a fatty acid sometimes denoted 18:2 (n−6) or 18:2 cis-9,12. A linoleate is a salt or ester of this acid.[5]

Linoleic acid is a polyunsaturated, omega−6 fatty acid. It is a colorless liquid that is virtually insoluble in water but soluble in many organic solvents.[2] It typically occurs in nature as a triglyceride (ester of glycerin) rather than as a free fatty acid.[6] It is one of two essential fatty acids for humans, who must obtain it through their diet,[7] and the most essential, because the body uses it as a base to make the others.

The word "linoleic" derives from Latin linum 'flax' and oleum 'oil', reflecting the fact that it was first isolated from linseed oil.

  1. ^ a b c The Merck Index, 11th Edition, 5382
  2. ^ a b c William M. Haynes (2016). CRC Handbook of Chemistry and Physics (97th ed.). Boca Raton: CRC Press. pp. 3–338. ISBN 978-1-4987-5429-3.
  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. ^ National Center for Biotechnology Information (2024). PubChem Compound Summary for CID 5280450, Linoleic Acid. Retrieved January 20, 2024 from https://pubchem.ncbi.nlm.nih.gov/compound/Linoleic-Acid.
  5. ^ "Fatty Acids". Cyber Lipid. Archived from the original on 28 October 2018. Retrieved 31 July 2017.
  6. ^ Mattes, Richard D. (2009). "Is there a fatty acid taste?". Annual Review of Nutrition. 29: 305–327. doi:10.1146/annurev-nutr-080508-141108. PMC 2843518. PMID 19400700.
  7. ^ Simopoulos, Artemis P. (2008). "The importance of the omega-6/omega-3 fatty acid ratio in cardiovascular disease and other chronic diseases". Experimental Biology and Medicine. 233 (6): 674–688. doi:10.3181/0711-mr-311. PMID 18408140. S2CID 9044197.

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