Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 13:51:24 -0600 |
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Update Date | 2015-10-02 02:25:49 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | alpha-Linolenic acid |
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Description | Alpha-linolenic acid (ALA) is a polyunsaturated fatty acid (PUFA). It is a member of the group of essential fatty acids called omega-3 fatty acids. Omega-3 fatty acids get their name based on the location of one of their first double bond. In all omega-3 fatty acids, the first double bond is located between the third and fourth carbon atom counting from the methyl end of the fatty acid (n-3). Omega-3 fatty acids can modulate the expression of a number of genes, including those involved with fatty acid metabolism. Alpha linolenic acid and other omega 3 fatty acids may regulate gene expression by interacting with specific transcription factors. ALA is an intermediate in alpha-Linolenic acid metabolism and biosynthesis of unsaturated fatty acids pathway in E. coli (KEGG compound: C06427). |
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Structure | |
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Synonyms: | - (9,12,15)-linolenate
- (9,12,15)-linolenic acid
- (9E,12E,15E)-9,12,15-Octadecatrienoate
- (9E,12E,15E)-9,12,15-Octadecatrienoic acid
- (9Z,12Z,15Z)-Octadecatrienoate
- (9Z,12Z,15Z)-Octadecatrienoic acid
- (Z,Z,Z)-9,12,15-Octadecatrienoate
- (Z,Z,Z)-9,12,15-Octadecatrienoic acid
- 9,12,15-Octadecatrienoate
- 9,12,15-Octadecatrienoic acid
- 9-cis,12-cis,15-cis-Octadecatrienoate
- 9-cis,12-cis,15-cis-Octadecatrienoic acid
- 9Z,12Z,15Z-octadecatrienoate
- 9Z,12Z,15Z-octadecatrienoic acid
- A-Linolenate
- A-Linolenic acid
- All-cis-9,12,15-Octadecatrienoate
- All-cis-9,12,15-Octadecatrienoic acid
- alpha-Linolenate
- Alpha-Linolenic acid
- Cis,cis,cis-9,12,15-Octadecatrienoate
- Cis,cis,cis-9,12,15-Octadecatrienoic acid
- Cis-9,12,15-Octadecatrienoate
- Cis-9,12,15-Octadecatrienoic acid
- Industrene 120
- Linolenate
- Linolenic acid
- α-Linolenate
- α-Linolenic acid
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Chemical Formula: | C18H30O2 |
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Weight: | Average: 278.4296 Monoisotopic: 278.224580204 |
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InChI Key: | DTOSIQBPPRVQHS-UHFFFAOYSA-N |
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InChI: | InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20) |
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CAS number: | 463-40-1 |
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IUPAC Name: | (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid |
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Traditional IUPAC Name: | α linolenic acid |
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SMILES: | CCC=CCC=CCC=CCCCCCCCC(O)=O |
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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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Charge: | -1 |
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Melting point: | -16.5 °C |
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Experimental Properties: | Property | Value | Source |
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LogP: | 6.46 [SANGSTER (1993)] | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Membrane |
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Reactions: | |
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SMPDB Pathways: | Not Available |
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KEGG Pathways: | - Biosynthesis of unsaturated fatty acids ec01040
- alpha-Linolenic acid metabolism ec00592
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EcoCyc Pathways: | Not Available |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) | splash10-052f-7900000000-8765cf82603feb1b448f | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) | splash10-004i-9300000000-302519a616eaed5fcc59 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-005c-9800000000-2d44b3c70e2992b9a812 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-052f-7900000000-8765cf82603feb1b448f | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-004i-9300000000-302519a616eaed5fcc59 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-005c-9800000000-2d44b3c70e2992b9a812 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-052f-5900000000-28710ea35f196c595e03 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-052e-6950000000-27037263e74c8119ead0 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00ds-6931000000-657fa0cc66a206a36409 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated) | splash10-004i-0190000000-aee97e9ea2c7f0783adf | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated) | splash10-05nb-9500000000-fb92aefc701027239359 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated) | splash10-0aru-9100000000-a5dddfe6f629d1371fac | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-004i-0090000000-2b7bea03a685454dd135 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-004i-0090000000-53ddfaed6ce13c37d957 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-004i-0090000000-e5350a66361bc63d1071 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-004i-0090000000-5731aa5e301022c06813 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-004i-0091010000-6922411e48d747e592b5 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , negative | splash10-001i-0090000000-a18b573ad888d048efa6 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-004i-0090000000-2b7bea03a685454dd135 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-004i-0090000000-e5350a66361bc63d1071 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-004i-0090000000-5731aa5e301022c06813 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive | splash10-004i-0090000000-1d391027db3704d71cb9 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive | splash10-00lr-9210000000-41acd8a55f52afec6d79 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 40V, positive | splash10-014i-9000000000-a976b4a80a07eb2c4641 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9100000000-497eddf5d738a45f83fb | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0090000000-0c00ca98901526cb2e26 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-004i-1090000000-35ffce9343fe0d15ea0d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-004i-0090000000-373584fbab950d6676cc | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01t9-0090000000-ae1f482177d0e208165e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00o0-5690000000-20804c8382f14ff0ccf4 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-014l-8930000000-9d5e342b1351adc71c20 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0090000000-4d3e8d1180800a7b4ed5 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0059-1090000000-67ab14c068a142dd3c30 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9230000000-403c610d63380e63109a | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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References: | - Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
- Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
- Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
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Synthesis Reference: | Li, Guihua; Qian, Xiangming; Jiang, Yanchao; Ma, Shushi. Preparation of a-linolenic acid from linseed oil. Zhengzhou Gongcheng Xueyuan Xuebao (2004), 25(3), 13-15. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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Links |
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External Links: | |
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