Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:16 UTC |
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Update date | 2019-11-26 03:07:15 UTC |
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Primary ID | FDB012633 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | Myristoleic acid |
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Description | Occurs in natural fats, e.g. Cottonseed oil
Myristoleic acid is a monounsaturated fatty acid that represent approximately 0.3 - 0.7% of the total fatty acid composition of adipose tissue triacylglycerol in human. (PMID 10393134); It has been suggested that his cytotoxic and effective cell death inducer activity could be used for the treatment of prostate cancer. (PMID 11304730); Myristoleic acid, or 9-tetradecenoic acid, is an omega-5 fatty acid. It is biosynthesized from myristic acid by the enzyme delta-9 desaturase, but it is uncommon in nature. One of the major sources of this fatty acid is the seed oil from plants of the genus Myristicaceae, comprising up to 30 per cent of the oil in some species. Myristoleic acid is found in many foods, some of which are garfish, wheat, soup, and ginger. |
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CAS Number | 544-64-9 |
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Structure | |
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Synonyms | Synonym | Source |
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(9Z)-Tetradecenoic acid | ChEBI | (Z)-Tetradec-9-enoic acid | ChEBI | 9-Tetradecenoic acid | ChEBI | 9Z-Tetradecenoic acid | ChEBI | cis-9-Tetradecenoic acid | ChEBI | cis-Delta(9)-Tetradecenoic acid | ChEBI | cis-Tetradec-9-enoic acid | ChEBI | (9Z)-Tetradecenoate | Generator | (Z)-Tetradec-9-enoate | Generator | 9-Tetradecenoate | Generator | 9Z-Tetradecenoate | Generator | cis-9-Tetradecenoate | Generator | cis-delta(9)-Tetradecenoate | Generator | cis-Δ(9)-tetradecenoate | Generator | cis-Δ(9)-tetradecenoic acid | Generator | cis-Tetradec-9-enoate | Generator | Myristoleate | Generator | (9Z)-Tetradec-9-enoate | HMDB | (9Z)-Tetradec-9-enoic acid | HMDB | (9Z)-9-Tetradecenoic acid | HMDB | (Z)-9-Tetradecenoic acid | HMDB | 9(Z)-Tetradecenoic acid | HMDB | 9-cis-Tetradecenoic acid | HMDB | FA(14:1(9Z)) | HMDB | FA(14:1n5) | HMDB | Myristoleic acid | HMDB | Myristolenic acid | HMDB | Oleomyristic acid | HMDB | cis-delta9-Tetradecenoic acid | HMDB | cis-Δ9-Tetradecenoic acid | HMDB | (9Z)-tetradec-9-enoate | biospider | (9Z)-tetradec-9-enoic acid | biospider | 9-Tetradecenoic acid, (9Z)- | biospider | 9-Tetradecenoic acid, (Z)- | biospider | 9Z-tetradecenoate | biospider | 9Z-tetradecenoic acid | biospider | cis-9-tetradecenoate | biospider | cis-9-tetradecenoic acid | biospider | cis-Delta(9)-tetradecenoate | biospider | cis-Delta(9)-tetradecenoic acid | biospider | cis-δ(9)-tetradecenoate | Generator | cis-δ(9)-tetradecenoic acid | Generator | Z-9-Tetradecenoic acid | biospider |
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Predicted Properties | |
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Chemical Formula | C14H26O2 |
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IUPAC name | (9Z)-tetradec-9-enoic acid |
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InChI Identifier | InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h5-6H,2-4,7-13H2,1H3,(H,15,16)/b6-5- |
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InChI Key | YWWVWXASSLXJHU-WAYWQWQTSA-N |
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Isomeric SMILES | CCCC\C=C/CCCCCCCC(O)=O |
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Average Molecular Weight | 226.355 |
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Monoisotopic Molecular Weight | 226.193280076 |
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Classification |
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Description | Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. |
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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 | Fatty acids and conjugates |
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Direct Parent | Long-chain fatty acids |
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Alternative Parents | |
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Substituents | - Long-chain 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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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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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 74.29%; H 11.58%; O 14.14% | DFC |
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Melting Point | Mp -4.5° | DFC |
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Boiling Point | Bp0.03 133° | DFC |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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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 | Not Available | |
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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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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0aou-9100000000-1823acbf402fe87fba5b | 2015-03-01 | View Spectrum | Predicted GC-MS | Myristolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-9800000000-71fb52f9fefd5cb3790e | Spectrum | Predicted GC-MS | Myristolic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00a9-9520000000-b85c6ba98a1ce24c3518 | Spectrum | Predicted GC-MS | Myristolic 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 - LC-ESI-QQ , negative | splash10-004i-0090000000-57b079c6d11a9714cb51 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-0090000000-4fcda40660e1f5947eb6 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-9120000000-50121015a2477be41bec | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0595-9000000000-98c3d58fb9e1e7c41c90 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , negative | splash10-004i-0090000000-e588f40ae851251aee81 | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-056r-0390000000-6a2bf4ff780562d5fdd9 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00lr-6930000000-bd53c7ac25c8930728e7 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9300000000-cd017bd3efd7fa06ee6e | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0190000000-c6a068748e37ad83d1d8 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0059-1590000000-999dd13c5871dbb32a3f | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9400000000-97121a85c8e202172ecf | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0090000000-6c6d923a7644bf907b73 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-056r-1090000000-bf30a380076470239567 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9300000000-b037435cdbd96f2e828d | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a7j-9330000000-790a04dc9533b3b6607b | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05o1-9000000000-fa6bdbb819001b908171 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0aou-9000000000-aaba2dc5fc19c49556c2 | 2021-09-22 | View Spectrum |
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NMR | Type | Description | | View |
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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 |
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External Links |
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ChemSpider ID | 4444564 |
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ChEMBL ID | CHEMBL456732 |
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KEGG Compound ID | C08322 |
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Pubchem Compound ID | 5281119 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 27781 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB02000 |
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CRC / DFC (Dictionary of Food Compounds) ID | CPB82-Z:HJL78-N |
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EAFUS ID | Not Available |
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Dr. Duke ID | MYRISTOLEIC-ACID |
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BIGG ID | Not Available |
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KNApSAcK ID | C00001229 |
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HET ID | Not Available |
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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 | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Myristoleic 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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antioxidant | 22586 | A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. | DUKE |
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Enzymes | Not Available |
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Pathways | Not Available |
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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 | Not Available |
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Files |
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MSDS | Not Available |
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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). — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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