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Linoleic acid
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| 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)
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| 1727101 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.000.428 |
| EC Number |
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| 57557 | |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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) | |
| 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.
- ^ a b c The Merck Index, 11th Edition, 5382
- ^ 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.
- ^ a b c d Record 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.
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