−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]
Solubility in water
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)
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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Infobox references
Chemical compound
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.
^ abcThe Merck Index, 11th Edition, 5382
^ abcWilliam M. Haynes (2016). CRC Handbook of Chemistry and Physics (97th ed.). Boca Raton: CRC Press. pp. 3–338. ISBN 978-1-4987-5429-3.
^ abcdRecord of CAS RN 60-33-3 in the GESTIS Substance Database of the Institute for Occupational Safety and Health
^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.
^"Fatty Acids". Cyber Lipid. Archived from the original on 28 October 2018. Retrieved 31 July 2017.
^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.
^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.
Linoleicacid (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...
Conjugated linoleicacids (CLA) are a family of isomers of linoleicacid. In principle, 28 isomers are possible. CLA is found mostly in the meat and dairy...
two fatty acids are known to be essential for humans: alpha-linolenic acid (an omega-3 fatty acid) and linoleicacid (an omega-6 fatty acid). These are...
essential fatty acids are known to be essential for humans: alpha-linolenic acid (an omega-3 fatty acid) and linoleicacid (an omega-6 fatty acid). The biological...
are isomers of linoleicacid with double bonds separated by one single bond. They are named conjugated linoleicacids. Eicosadienoic acid (eicosadienoic's)...
carbon. The illustration below shows the omega-6 fatty acid, linoleicacid. Polyunsaturated fatty acids can be classified in various groups by their chemical...
6 fatty acid, also known as linoleicacid, is found in poultry fat and the oil from safflower, sunflower, corn and flaxseed. Arachidonic acid is a well...
Conjugated fatty acids include isomers of linoleicacid. Conjugated analogues linoleicacids are the most investigated conjugated fatty acids. Some conjugated...
oleic acid, with one double bond, has a "kink" in it, whereas linoleicacid, with two double bonds, has a more pronounced bend. α-Linolenic acid, with...
emollient. Sunflower oil is primarily composed of linoleicacid, a polyunsaturated fat, and oleic acid, a monounsaturated fat. Through selective breeding...
fatty acid. For example, Δ6 desaturation introduces a double bond between carbons 6 and 7 of linoleicacid (LA C18H32O2; 18:2-n6) and α-linolenic acid (ALA:...
sapienic acid levels in sebum. Delta-6-desaturation of palmitic acid leads to the biosynthesis of sapienic acid. In other tissues linoleicacid is the target...
Linolelaidic acid is an omega-6 trans fatty acid (TFA) and is a cis–trans isomer of linoleicacid. It is found in partially hydrogenated vegetable oils...
reflects singlet oxygen attack on linoleicacid. In addition to serving as markers, the linoleic and arachidonic acid products can contribute to tissue...
Rumenic acid, also known as bovinic acid, is a conjugated linoleicacid (CLA) found in the fat of ruminants and in dairy products. It is an omega-7 trans...
Punicic acid is a conjugated linolenic acid or CLnA; i.e. it has three conjugated double bonds. It is chemically similar to the conjugated linoleicacids, or...
convert it into rumenic acid, a conjugated linoleicacid, where it shows anticarcinogenic properties. Its stereoisomer, cis-vaccenic acid, is found in Sea Buckthorn...
mixture of triglycerides in which about 90% of fatty acids are ricinoleates. Oleic acid and linoleicacid are the other significant components. Castor oil...
Salicylic acid is an organic compound with the formula HOC6H4COOH. A colorless (or, white), bitter-tasting solid, it is a precursor to and a metabolite...
an omega-3 (n-3) fatty acid γ-Linolenic acid, an omega-6 (n-6) fatty acidLinoleicacid, the similarly named essential fatty acid This set index article...
calorie-rich, with an especially high content of fat (particularly linoleicacid and oleic acid), protein, dietary fiber, and numerous micronutrients. Pumpkin...
its black, crunchy seeds. The seed oil contains the fatty acidslinoleicacid and linolenic acid. Dragon fruit is used to flavor and color juices and alcoholic...
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