| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:34:43 UTC |
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| Update Date | 2020-06-04 22:31:33 UTC |
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| MCDB ID | BMDB0000673 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Linoleic acid |
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| Description | Linoleic acid, also known as LA or linoleate, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Linoleic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Linoleic acid exists in all living organisms, ranging from bacteria to humans. Linoleic acid is a potentially toxic compound. Linoleic acid has been found to be associated with several diseases known as hypertension, ulcerative colitis, essential hypertension, and thyroid cancer; also linoleic acid has been linked to the inborn metabolic disorders including isovaleric acidemia. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (9Z,12Z)-Octadecadienoic acid | ChEBI | | (Z,Z)-9,12-Octadecadienoic acid | ChEBI | | 9-cis,12-cis-Octadecadienoic acid | ChEBI | | 9Z,12Z-Octadecadienoic acid | ChEBI | | Acide cis-linoleique | ChEBI | | Acide linoleique | ChEBI | | Acido linoleico | ChEBI | | all-cis-9,12-Octadecadienoic acid | ChEBI | | C18:2 9C, 12C Omega6 todos cis-9,12-octadienoico | ChEBI | | C18:2, N-6,9 all-cis | ChEBI | | cis,cis-9,12-Octadecadienoic acid | ChEBI | | cis,cis-Linoleic acid | ChEBI | | cis-Delta(9,12)-Octadecadienoic acid | ChEBI | | LA | ChEBI | | Linolic acid | ChEBI | | 9-cis,12-cis-Octadecadienoate | Kegg | | (9Z,12Z)-Octadecadienoate | Generator | | (Z,Z)-9,12-Octadecadienoate | Generator | | 9Z,12Z-Octadecadienoate | Generator | | all-cis-9,12-Octadecadienoate | Generator | | cis,cis-9,12-Octadecadienoate | Generator | | cis,cis-Linoleate | Generator | | cis-delta(9,12)-Octadecadienoate | Generator | | cis-Δ(9,12)-octadecadienoate | Generator | | cis-Δ(9,12)-octadecadienoic acid | Generator | | Linolate | Generator | | Linoleate | Generator | | (9Z,12Z)-9,12-Octadecadienoate | HMDB | | (9Z,12Z)-9,12-Octadecadienoic acid | HMDB | | 9-cis,12-cis-Linoleate | HMDB | | 9-cis,12-cis-Linoleic acid | HMDB | | 9Z,12Z-Linoleate | HMDB | | 9Z,12Z-Linoleic acid | HMDB | | cis-9,cis-12-Octadecadienoate | HMDB | | cis-9,cis-12-Octadecadienoic acid | HMDB | | cis-D9,12-Octadecadienoate | HMDB | | cis-D9,12-Octadecadienoic acid | HMDB | | Emersol 315 | HMDB | | Extra linoleic 90 | HMDB | | Polylin 515 | HMDB | | Unifac 6550 | HMDB | | Acid, 9,12-octadecadienoic | HMDB | | Linoelaidic acid | HMDB | | Linoleic acid, (e,e)-isomer | HMDB | | Linoleic acid, (Z,Z)-isomer | HMDB | | Linoleic acid, (Z,Z)-isomer, 14C-labeled | HMDB | | Linoleic acid, ammonium salt, (Z,Z)-isomer | HMDB | | Linoleic acid, potassium salt, (Z,Z)-isomer | HMDB | | 9 trans,12 trans Octadecadienoic acid | HMDB | | 9-trans,12-trans-Octadecadienoic acid | HMDB | | Linoleic acid, sodium salt, (e,e)-isomer | HMDB | | Linoleic acid, sodium salt, (Z,Z)-isomer | HMDB | | trans,trans-9,12-Octadecadienoic acid | HMDB | | 9,12-Octadecadienoic acid | HMDB | | Linoelaidic acid, (e,Z)-isomer | HMDB | | Linoleic acid, calcium salt, (Z,Z)-isomer | HMDB | | Linolelaidic acid | HMDB | | 9,12 Octadecadienoic acid | HMDB | | Linoleic acid, (Z,e)-isomer | HMDB | | FA(18:2(9Z,12Z)) | HMDB |
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| Chemical Formula | C18H32O2 |
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| Average Molecular Weight | 280.4455 |
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| Monoisotopic Molecular Weight | 280.240230268 |
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| IUPAC Name | (9Z,12Z)-octadeca-9,12-dienoic acid |
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| Traditional Name | linoleic |
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| CAS Registry Number | 60-33-3 |
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| SMILES | CCCCC\C=C/C\C=C/CCCCCCCC(O)=O |
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| InChI Identifier | 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- |
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| InChI Key | OYHQOLUKZRVURQ-HZJYTTRNSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Fatty Acyls |
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| Sub Class | Lineolic acids and derivatives |
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| Direct Parent | Lineolic acids and derivatives |
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| Alternative Parents | |
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| Substituents | - Octadecanoid
- Long-chain fatty acid
- Fatty acid
- Unsaturated fatty acid
- Straight chain fatty acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Liquid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | -8.5 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | 7.05 | SANGSTER (1993) |
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| Predicted Properties | |
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| Spectra |
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| | Spectrum Type | Description | Splash Key | Deposition Date | View |
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| GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) | splash10-000t-7900000000-b6ee03c4800464c37471 | 2014-06-16 | View Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) | splash10-00vi-9300000000-c92dac639ced59eb5dbe | 2014-06-16 | View Spectrum | | GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-003s-9700000000-77e67d7b1a161e6ecfa6 | 2014-06-16 | View Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-000t-7900000000-b6ee03c4800464c37471 | 2017-09-12 | View Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00vi-9300000000-c92dac639ced59eb5dbe | 2017-09-12 | View Spectrum | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-003s-9700000000-77e67d7b1a161e6ecfa6 | 2017-09-12 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0007-9750000000-50d69948d56dd2ba6e42 | 2017-09-01 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0079-9631000000-cc93c24bbf14d81ae9b6 | 2017-10-06 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0f89-0190000000-2be9501b1d4a9fcbd1c0 | 2012-07-24 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0uk9-0790000000-7f6e35a591f977bc488e | 2012-07-24 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0udi-0090000000-c56edc2bbf9d6752aec5 | 2012-07-24 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - FAB-EBEB (JMS-HX/HX 110A, JEOL) , Negative | splash10-004i-0090000000-baf4579e26c6b393d391 | 2012-08-31 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-004i-0090000000-815c1682b2c59ba96f10 | 2012-08-31 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-004i-0090000000-3406b2b2d5756807e1cd | 2012-08-31 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-004i-0090000000-2fb4975278fa4d118f43 | 2012-08-31 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0a6r-9380000000-37f833673c248405c8ef | 2012-08-31 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0a4i-9200000000-7d34ed5900a17ffe3f9b | 2012-08-31 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-004i-0090010000-f8df6099e003402f2566 | 2017-08-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-004i-0091021000-0e44779958d5744d873b | 2017-08-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-004i-0091021000-0e44779958d5744d873b | 2017-08-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-004i-0091021000-0e44779958d5744d873b | 2017-08-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-004i-0091021000-0e44779958d5744d873b | 2017-08-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-004i-0090010000-f8df6099e003402f2566 | 2017-09-12 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-004i-0091021000-0e44779958d5744d873b | 2017-09-12 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-004i-0090000000-adbf36f0a17c33ac33f8 | 2017-09-12 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-004i-0090000000-2747c83af78732eb6e16 | 2017-09-12 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-004i-0090000000-a0415b1cb63b4562b40e | 2017-09-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0090000000-8bdf8d54a29f73494242 | 2017-09-01 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0239-4590000000-e5ee57553b064eae2efe | 2017-09-01 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00rf-9830000000-b26ba057a2b4d135b478 | 2017-09-01 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0090000000-f1e9e4b543f7d4f48bf8 | 2017-09-01 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01ti-0090000000-665523c6142ff4e39c96 | 2017-09-01 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9240000000-dca36a25ad7519d500c3 | 2017-09-01 | View Spectrum | | MS | Mass Spectrum (Electron Ionization) | splash10-015a-9200000000-a193c27810bedf93c498 | 2014-09-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Not Available | 2012-12-04 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | Not Available | 2014-09-20 | View Spectrum | | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | Not Available | 2012-12-05 | View Spectrum |
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| Concentrations |
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| Detected and Quantified | 3209 +/- 1069 uM | Total fatty acid | | details | | Detected but not Quantified | Not Applicable | | | details | | Detected and Quantified | 1854 +/- 392 uM | Total fatty acid | | details | | Detected and Quantified | 2816 +/- 678 uM | Total fatty acid | | details | | Detected and Quantified | 1747 +/- 357 uM | Total fatty acid | | details | | Detected and Quantified | 2674 +/- 570 uM | Total fatty acid | | details | | Detected but not Quantified | Not Applicable | | | details | | Detected but not Quantified | Not Applicable | | | details | | Detected and Quantified | 214 uM | Total fatty acid | | details | | Detected and Quantified | 178 uM | Total fatty acid | | details | | Detected and Quantified | 214 uM | Total fatty acid | | details | | Detected and Quantified | 2567 uM | Total fatty acid | | details | | Detected and Quantified | 3779 uM | Total fatty acid | | details | | Detected and Quantified | 3779 uM | Total fatty acid | | details | | Detected but not Quantified | Not Applicable | | | details | | Detected but not Quantified | Not Applicable | | | details | | Detected and Quantified | 21394 uM | Total fatty acid | | details | | Detected and Quantified | 26387 uM | Total fatty acid | | details | | Detected and Quantified | 27456 uM | Total fatty acid | | details | | Detected and Quantified | 28882 uM | Total fatty acid | | details | | Detected and Quantified | 10.56 +/- 1.06 uM | Free fatty acid | | details | | Detected and Quantified | 10.03 +/- 1.06 uM | Free fatty acid | | details | | Detected and Quantified | 3.17 +/- 0.53 uM | Free fatty acid | | details | | Detected and Quantified | 9.49 +/- 0.08 uM | Free fatty acid | | details | | Detected and Quantified | 7.04 +/- 0.14 uM | Free fatty acid | | details | | Detected and Quantified | 14 +/- 1 uM | Free fatty acid | | details | | Detected and Quantified | 14 +/- 1 uM | Free fatty acid | | details | | Detected and Quantified | 12.4 +/- 0.3 uM | Free fatty acid | | details |
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| External Links |
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| HMDB ID | HMDB0000673 |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FoodDB ID | FDB006287 |
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| KNApSAcK ID | C00001224 |
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| Chemspider ID | 4444105 |
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| KEGG Compound ID | C01595 |
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| BioCyc ID | LINOLEIC_ACID |
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| BiGG ID | 37956 |
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| Wikipedia Link | Linoleic_acid |
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| METLIN ID | 191 |
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| PubChem Compound | 5280450 |
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| PDB ID | Not Available |
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| ChEBI ID | 17351 |
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| References |
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| Synthesis Reference | Walborsky, Harry M.; Davis, Robert H.; Howton, David R. A total synthesis of linoleic acid. Journal of the American Chemical Society (1951), 73 2590-4. |
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| Material Safety Data Sheet (MSDS) | Download (PDF) |
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| General References | - Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2. [PubMed:16899705 ]
- Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
- Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11. [PubMed:9718493 ]
- Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. [PubMed:1779072 ]
- Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. [PubMed:20855010 ]
- Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93. [PubMed:5409465 ]
- van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21. [PubMed:28219465 ]
- Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
- M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189. Chemometrics and Intelligent Laboratory Systems.
- Lawrence K. Creamer, Alastair K.H. MacGibbon (1996). Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568 doi: 10.1016/0958-6946(96)85309-X. International Dairy Journal.
- M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri (2014). M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021. Livestock Science.
- Fooddata+, The Technical University of Denmark (DTU) [Link]
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