Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-05-22 14:17:35 UTC |
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Update Date | 2022-03-07 02:49:12 UTC |
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HMDB ID | HMDB0002080 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Petroselinic acid |
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Description | Petroselinic acid, also known as (6Z)-Octadecenoic acid, is an 18-carbon unsaturated fatty acid that occurs naturally in several animal and vegetable fats and oils. It is a white powder and is commercially available. In chemical terms, petroselinic acid is classified as a monounsaturated omega-12 fatty acid, abbreviated as 18:1 cis-6. Petroselinic acid is a positional isomer of oleic acid. The term "petroselinic" means related to, or derived from, oil of Petroselinum, or oil of parsley. Petroselinic acid was first isolated from parsley seed oil in 1909. Petroselinic acid occurs in high amounts in plants in the Apiaceae family (a family of mostly aromatic flowering plants named after the genus Apium and commonly known as the celery, carrot or parsley family), Araliaceae (a family of flowering plants composed of about 43 genera and around 1500 species consisting of primarily woody plants and some herbaceous plants), Griselinia (Griseliniaceae) and in Garryaceae. The occurrence of petroselinic acid as the major fatty acid is used in chemosystematics as a proof of a close relationship of several families within the Apiales as well as within the Garryales. Petroselonic acid has been found in coriander (Coriandrum sativum) and cumin (Cuminum cyminum) and caraway seeds. In addition, petroselinic acid has been found in minor amounts in several fats of plant and animal origin, including in human sources. Petroselinic acid is an important oleochemical material for the food, cosmetics, chemistry and pharmaceutical industry (PMID: 16604360 ) as it can be easily processed into lauric and adipinic acid. |
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Structure | InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h12-13H,2-11,14-17H2,1H3,(H,19,20) |
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Synonyms | Value | Source |
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18:1N-6 | ChEBI | 6-Octadecensaeure | ChEBI | C18:1N-6 | ChEBI | Octadec-6-ensaeure | ChEBI | Petroselinate | Generator | Octadec-6-enoate | HMDB | Petroselinic acid, (e)-isomer | HMDB | Petroselinic acid, sodium salt, (Z)-isomer | HMDB | Petroselenic acid | HMDB | Petroselinic acid, (Z)-isomer | HMDB | Petroselinic acid | MeSH |
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Chemical Formula | C18H34O2 |
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Average Molecular Weight | 282.468 |
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Monoisotopic Molecular Weight | 282.255880335 |
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IUPAC Name | octadec-6-enoic acid |
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Traditional Name | 6-octadecenoic acid |
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CAS Registry Number | 593-39-5 |
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SMILES | CCCCCCCCCCCC=CCCCCC(O)=O |
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InChI Identifier | InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h12-13H,2-11,14-17H2,1H3,(H,19,20) |
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InChI Key | CNVZJPUDSLNTQU-UHFFFAOYSA-N |
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Chemical Taxonomy |
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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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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Petroselinic acid GC-MS (1 TMS) | splash10-015a-5900000000-b74b3a322c8500719900 | 2018-05-25 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Petroselinic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Petroselinic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0536-9200000000-566b9687fd3f631b2d76 | 2018-05-25 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Petroselinic acid 10V, Positive-QTOF | splash10-014i-0090000000-92eaf2fd267975519c73 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Petroselinic acid 20V, Positive-QTOF | splash10-014r-3590000000-a09c373d95774671d77a | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Petroselinic acid 40V, Positive-QTOF | splash10-006x-9830000000-5407ff71f907bbcff81e | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Petroselinic acid 10V, Negative-QTOF | splash10-001i-0090000000-1b80c5a75129c09b94ae | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Petroselinic acid 20V, Negative-QTOF | splash10-01qi-0090000000-594a087f3d32d156a36b | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Petroselinic acid 40V, Negative-QTOF | splash10-0a4l-9130000000-ca75de66449608dc0999 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Petroselinic acid 10V, Negative-QTOF | splash10-001i-0090000000-8b8562cadde7e7a8ba4f | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Petroselinic acid 20V, Negative-QTOF | splash10-01q9-1090000000-594ebc89873b9a07daab | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Petroselinic acid 40V, Negative-QTOF | splash10-0006-9120000000-53ca828fdedf1b6b5354 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Petroselinic acid 10V, Positive-QTOF | splash10-00lr-2290000000-b0d2eeeebe9b395823a6 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Petroselinic acid 20V, Positive-QTOF | splash10-05nb-9520000000-a105cfcc2e8bdbf85fe6 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Petroselinic acid 40V, Positive-QTOF | splash10-0a4m-9000000000-4f913ba39936bf42fbe3 | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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