| Record Information |
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| Version | 1.0 |
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| Created at | 2006-05-22 14:17:35 UTC |
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| Updated at | 2024-05-05 00:32:37 UTC |
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| NP-MRD ID | NP0000010 |
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| Secondary Accession Numbers | None |
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| Natural Product 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 | |
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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 Mass | 282.4680 Da |
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| Monoisotopic Mass | 282.25588 Da |
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| IUPAC Name | Not Available |
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| Traditional Name | Not Available |
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| CAS Registry Number | 593-39-5 |
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| SMILES | Not Available |
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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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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-05-03 | View Spectrum | | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-05-03 | View Spectrum | | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-05-03 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-05-03 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-05-03 | View Spectrum |
| | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-05-03 | View Spectrum |
| | Species |
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| Species of Origin | |
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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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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 29.8 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | Not Available |
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| General References | - Metzger JO, Bornscheuer U: Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification. Appl Microbiol Biotechnol. 2006 Jun;71(1):13-22. Epub 2006 Apr 8. [PubMed:16604360 ]
- Ping F, Li Y, Cao Y, Shang J, Zhang Z, Yuan Z, Wang W, Guo Y: Metabolomics Analysis of the Development of Sepsis and Potential Biomarkers of Sepsis-Induced Acute Kidney Injury. Oxid Med Cell Longev. 2021 Apr 23;2021:6628847. doi: 10.1155/2021/6628847. eCollection 2021. [PubMed:33981387 ]
- Saini RK, Assefa AD, Keum YS: Spices in the Apiaceae Family Represent the Healthiest Fatty Acid Profile: A Systematic Comparison of 34 Widely Used Spices and Herbs. Foods. 2021 Apr 14;10(4). pii: foods10040854. doi: 10.3390/foods10040854. [PubMed:33920058 ]
- Erbiai EH, da Silva LP, Saidi R, Lamrani Z, Esteves da Silva JCG, Maouni A: Chemical Composition, Bioactive Compounds, and Antioxidant Activity of Two Wild Edible Mushrooms Armillaria mellea and Macrolepiota procera from Two Countries (Morocco and Portugal). Biomolecules. 2021 Apr 14;11(4). pii: biom11040575. doi: 10.3390/biom11040575. [PubMed:33920034 ]
- Berriozabalgoitia A, Gordoa JCR, Renobales M, Amores G, Barron LJR, Amiano P, Dorronsoro M, Perea Z, Virto M: The Sum of Plasma Fatty Acids iso16:0, iso17:0, trans11-18:1, cis9, trans11-CLA, and cis6-18:1 as Biomarker of Dairy Intake Established in an Intervention Study and Validated in the EPIC Cohort of Gipuzkoa. Nutrients. 2021 Feb 22;13(2). pii: nu13020702. doi: 10.3390/nu13020702. [PubMed:33671693 ]
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