Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:11 UTC |
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Update date | 2020-09-17 15:31:13 UTC |
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Primary ID | FDB012462 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB 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. alpha-Linolenic acid is not synthesized by mammals and therefore is an essential dietary requirement for all mammals. Omega-3 fatty acids get their name based on the location of one of their first double bonds. 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). Although humans and other mammals can synthesize saturated and some monounsaturated fatty acids from carbon groups in carbohydrates and proteins, they lack the enzymes necessary to insert a cis double bond at the n-6 or the n-3 position of a fatty acid. Certain nuts (English walnuts) and vegetable oils (canola, soybean, flaxseed/linseed, olive) are rich in alpha-linolenic acid. Omega-3 fatty acids like alpha-linolenic acid are important structural components of cell membranes. When incorporated into phospholipids, they affect cell membrane properties such as fluidity, flexibility, permeability, and the activity of membrane-bound enzymes. Omega-3 fatty acids can modulate the expression of several genes, including those involved with fatty acid metabolism and inflammation. alpha-Linolenic acid and other omega-3 fatty acids may regulate gene expression by interacting with specific transcription factors, including peroxisome proliferator-activated receptors (PPARs) and liver X receptors (LXRs). alpha-Linolenic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism. Patients with isovaleric acidemia have a defect in leucine catabolism resulting from a deficiency in the enzyme isovaleryl-CoA dehydrogenase. These patients do well on a low protein/low leucine diet but a low protein diet can lead to deficiencies in essential fatty acids, such as alpha-linolenic acid ( https://doi.org/10.1038/ejcn.2016.100). |
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CAS Number | 463-40-1 |
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Structure | |
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Synonyms | Synonym | Source |
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(9,12,15)-Linolenic acid | ChEBI | (9Z,12Z,15Z)-Octadecatrienoic acid | ChEBI | (Z,Z,Z)-9,12,15-Octadecatrienoic acid | ChEBI | 9,12,15-Octadecatrienoic acid | ChEBI | 9-cis,12-cis,15-cis-Octadecatrienoic acid | ChEBI | ALA | ChEBI | all-cis-9,12,15-Octadecatrienoic acid | ChEBI | cis,cis,cis-9,12,15-Octadecatrienoic acid | ChEBI | cis-Delta(9,12,15)-Octadecatrienoic acid | ChEBI | Linolenic acid | ChEBI | Linolenate | Kegg | alpha-Linolenate | Kegg | (9,12,15)-Linolenate | Generator | (9Z,12Z,15Z)-Octadecatrienoate | Generator | (Z,Z,Z)-9,12,15-Octadecatrienoate | Generator | 9,12,15-Octadecatrienoate | Generator | 9-cis,12-cis,15-cis-Octadecatrienoate | Generator | all-cis-9,12,15-Octadecatrienoate | Generator | cis,cis,cis-9,12,15-Octadecatrienoate | Generator | cis-delta(9,12,15)-Octadecatrienoate | Generator | cis-Δ(9,12,15)-octadecatrienoate | Generator | cis-Δ(9,12,15)-octadecatrienoic acid | Generator | a-Linolenate | Generator | a-Linolenic acid | Generator | Α-linolenate | Generator | Α-linolenic acid | Generator | alpha Linolenic acid | HMDB | cis-9,12,15-Octadecatrienoate | HMDB | cis-9,12,15-Octadecatrienoic acid | HMDB | Industrene 120 | HMDB | FA(18:3(9Z,12Z,15Z)) | HMDB | FA(18:3n3) | HMDB | α-Linolenic acid | biospider | 9,12,15-Octadecatrienoic acid, (Z,Z,Z)- | biospider | 9Z,12Z,15Z-Octadecatrienoate | biospider | 9Z,12Z,15Z-Octadecatrienoic acid | biospider | alpha-Linolenic acid | biospider | cis-δ(9,12,15)-octadecatrienoate | Generator | cis-δ(9,12,15)-octadecatrienoic acid | Generator | α-linolenate | Generator | α-linolenic acid | Generator |
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Predicted Properties | |
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Chemical Formula | C18H30O2 |
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IUPAC name | (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid |
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InChI Identifier | 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)/b4-3-,7-6-,10-9- |
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InChI Key | DTOSIQBPPRVQHS-PDBXOOCHSA-N |
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Isomeric SMILES | CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O |
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Average Molecular Weight | 278.4296 |
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Monoisotopic Molecular Weight | 278.224580204 |
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Classification |
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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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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Foods | Nuts and legumes: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Liquid | |
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Physical Description | Not Available | |
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Mass Composition | C 77.65%; H 10.86%; O 11.49% | DFC |
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Melting Point | Mp -11.3° | DFC |
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Boiling Point | Bp0.05 125° | DFC |
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Experimental Water Solubility | Not Available | |
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Experimental logP | 6.46 | SANGSTER (1993) |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | d204 0.92 | DFC |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | alpha-Linolenic acid, 1 TMS, GC-MS Spectrum | splash10-052f-7900000000-8765cf82603feb1b448f | Spectrum | GC-MS | alpha-Linolenic acid, 1 TMS, GC-MS Spectrum | splash10-004i-9300000000-302519a616eaed5fcc59 | Spectrum | GC-MS | alpha-Linolenic acid, 1 TMS, GC-MS Spectrum | splash10-005c-9800000000-2d44b3c70e2992b9a812 | Spectrum | GC-MS | alpha-Linolenic acid, non-derivatized, GC-MS Spectrum | splash10-052f-7900000000-8765cf82603feb1b448f | Spectrum | GC-MS | alpha-Linolenic acid, non-derivatized, GC-MS Spectrum | splash10-004i-9300000000-302519a616eaed5fcc59 | Spectrum | GC-MS | alpha-Linolenic acid, non-derivatized, GC-MS Spectrum | splash10-005c-9800000000-2d44b3c70e2992b9a812 | Spectrum | GC-MS | alpha-Linolenic acid, non-derivatized, GC-MS Spectrum | splash10-052f-5900000000-28710ea35f196c595e03 | Spectrum | Predicted GC-MS | alpha-Linolenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-052e-6950000000-27037263e74c8119ead0 | Spectrum | Predicted GC-MS | alpha-Linolenic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00ds-6931000000-657fa0cc66a206a36409 | Spectrum | Predicted GC-MS | alpha-Linolenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated) | splash10-004i-0190000000-aee97e9ea2c7f0783adf | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated) | splash10-05nb-9500000000-fb92aefc701027239359 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated) | splash10-0aru-9100000000-a5dddfe6f629d1371fac | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-004i-0090000000-2b7bea03a685454dd135 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-004i-0090000000-53ddfaed6ce13c37d957 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-004i-0090000000-e5350a66361bc63d1071 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-004i-0090000000-5731aa5e301022c06813 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-004i-0091010000-6922411e48d747e592b5 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , negative | splash10-001i-0090000000-a18b573ad888d048efa6 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-004i-0090000000-2b7bea03a685454dd135 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-004i-0090000000-e5350a66361bc63d1071 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-004i-0090000000-5731aa5e301022c06813 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive | splash10-004i-0090000000-1d391027db3704d71cb9 | 2020-07-21 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive | splash10-00lr-9210000000-41acd8a55f52afec6d79 | 2020-07-21 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 40V, positive | splash10-014i-9000000000-a976b4a80a07eb2c4641 | 2020-07-21 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9100000000-497eddf5d738a45f83fb | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0090000000-0c00ca98901526cb2e26 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-004i-1090000000-35ffce9343fe0d15ea0d | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-004i-0090000000-373584fbab950d6676cc | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01t9-0090000000-ae1f482177d0e208165e | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00o0-5690000000-20804c8382f14ff0ccf4 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-014l-8930000000-9d5e342b1351adc71c20 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0090000000-4d3e8d1180800a7b4ed5 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0059-1090000000-67ab14c068a142dd3c30 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9230000000-403c610d63380e63109a | 2017-07-26 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 4444437 |
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ChEMBL ID | CHEMBL8739 |
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KEGG Compound ID | C06427 |
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Pubchem Compound ID | 5280934 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 27432 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB00132 |
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HMDB ID | HMDB01388 |
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CRC / DFC (Dictionary of Food Compounds) ID | CPM16-L:HHB80-W |
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EAFUS ID | Not Available |
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Dr. Duke ID | CIS-LINOLEIC-ACID|ALPHA-LINOLENIC-ACID|LINOLENIC-ACID |
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BIGG ID | 48237 |
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KNApSAcK ID | C00007247 |
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HET ID | LNL |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | rw1045911 |
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SuperScent ID | Not Available |
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Wikipedia ID | Alpha-Linolenic_acid |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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5alpha-reductase inhibitor | 50781 | An EC 1.3.1.* (oxidoreductase acting on CH-CH group of donor, NAD(+) or NADP(+) as acceptor) inhibitor that interferes with the action of of 3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+)), EC 1.3.1.22, the enzyme which converts testosterone (CHEBI:17347) into the more potent androgen 5alpha-dihydrotestosterone. | DUKE | anti aggregant | | | DUKE | anti hypertensive | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | anti leukotriene-D4 | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | anti menorrhagic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti metastatic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | anti prostatitic | | | DUKE | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | hypotensive | | | DUKE | immunostimulant | 50847 | A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity. | DUKE | lymphocytogenic | | | DUKE | propecic | | | DUKE | prostaglandin synthesis inhibitor | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | vasodilator | 35620 | A drug used to cause dilation of the blood vessels. | DUKE |
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Enzymes | Name | Gene Name | UniProt ID |
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Bile acid-CoA:amino acid N-acyltransferase | BAAT | Q14032 | Cytosolic acyl coenzyme A thioester hydrolase | ACOT7 | O00154 | Acyl-coenzyme A thioesterase 2, mitochondrial | ACOT2 | P49753 | Acyl-coenzyme A thioesterase 4 | ACOT4 | Q8N9L9 | Acyl-coenzyme A thioesterase 8 | ACOT8 | O14734 | Acyl-coenzyme A thioesterase 1 | ACOT1 | Q86TX2 | Elongation of very long chain fatty acids protein 4 | ELOVL4 | Q9GZR5 |
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Pathways | Name | SMPDB Link | KEGG Link |
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Alpha Linolenic Acid and Linoleic Acid Metabolism | SMP00018 | map00592 |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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faint |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| fatty |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| bitter |
- Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008). — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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