Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2023-02-21 17:14:46 UTC |
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HMDB ID | HMDB0000392 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 2-Octenoic acid |
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Description | 2-Octenoic acid, also known as 2-octenoate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. 2-Octenoic acid has 8 carbon atoms. 2-Octenoic acid is also known as an olefinic fatty acid carrying a double bond at position 2. It can exist in two isomeric forms, the cis and the trans form, with the trans or 2-E form being more abundant. 2-Octenoic acid is a relatively hydrophobic molecule with a water solubility of approximately 1 g/L. The 2E-isomer has a musty, sour, cheesy aroma and a fatty or waxy taste. 2-Octenoic acid is found in the human body and is naturally produced by hepatic microsomal oxidation of aliphatic aldehydes. 2-Octenoic acid has been detected in human urine and plasma (PMID 1883862 , 8087979 , 4086594 , 1417834 , 6480773 ). 2-Octenoic acid has also been identified as a potential pheromone excreted by the male abdominal glands of the cockroach Leucophaea maderae (PMID: 17200891 ). Outside the human body 2-Octenoic acid has been detected in coffee, cranberries, mushrooms, black tea and strawberries. It is also used as a food flavourant for baked goods and candies. |
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Structure | InChI=1S/C8H14O2/c1-2-3-4-5-6-7-8(9)10/h6-7H,2-5H2,1H3,(H,9,10)/b7-6- |
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Synonyms | Value | Source |
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2-Octenoate | Generator | cis-2-Octenoic acid | HMDB | (Z)-2-Octenoic acid | HMDB | 2-Octenic acid | HMDB | 2Z-Octenoate | HMDB | 2Z-Octenoic acid | HMDB | Oct-2-enoate | HMDB | Oct-2-enoic acid | HMDB | trans-2-Octenoate | HMDB | 2-Octenoic acid | HMDB |
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Chemical Formula | C8H14O2 |
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Average Molecular Weight | 142.1956 |
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Monoisotopic Molecular Weight | 142.099379692 |
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IUPAC Name | (2Z)-oct-2-enoic acid |
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Traditional Name | cis-2-octenoic acid |
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CAS Registry Number | 1577-96-4 |
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SMILES | CCCCC\C=C/C(O)=O |
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InChI Identifier | InChI=1S/C8H14O2/c1-2-3-4-5-6-7-8(9)10/h6-7H,2-5H2,1H3,(H,9,10)/b7-6- |
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InChI Key | CWMPPVPFLSZGCY-SREVYHEPSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 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 | Medium-chain fatty acids |
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Alternative Parents | |
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Substituents | - Medium-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 | Liquid |
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Experimental Molecular Properties | |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized | Show more...
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Spectra |
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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 - 2-Octenoic acid EI-B (Non-derivatized) | splash10-0096-9000000000-801c8e0537a0c78cb64f | 2018-05-25 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 2-Octenoic acid EI-B (Non-derivatized) | splash10-0096-9000000000-801c8e0537a0c78cb64f | 2018-05-25 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Octenoic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-054x-9100000000-685aa1c309f4024a258c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Octenoic acid GC-MS (1 TMS) - 70eV, Positive | splash10-05i3-9300000000-009fbcd018a04b967cd1 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Octenoic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Octenoic acid GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Octenoic acid Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-00di-9200000000-ea14afb080f00f6db329 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Octenoic acid Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-0fk9-9000000000-e4e0cfcba513035e593d | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Octenoic acid Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-0udi-9000000000-ff984717b537e96ab368 | 2012-07-24 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Octenoic acid 10V, Positive-QTOF | splash10-004i-1900000000-13db6226b25ca6e887e7 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Octenoic acid 20V, Positive-QTOF | splash10-003v-9400000000-5c8132b1452fb86685a6 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Octenoic acid 40V, Positive-QTOF | splash10-000f-9000000000-d964983e7540bbe985ae | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Octenoic acid 10V, Negative-QTOF | splash10-0006-1900000000-bdaae44d4773ffd6a29c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Octenoic acid 20V, Negative-QTOF | splash10-006y-3900000000-f923ee2d24c2c936a395 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Octenoic acid 40V, Negative-QTOF | splash10-052g-9100000000-3f6317b29935f491c0f3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Octenoic acid 10V, Positive-QTOF | splash10-0a4i-9100000000-35fbf6036a26b499b040 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Octenoic acid 20V, Positive-QTOF | splash10-0a4i-9000000000-a8d30352fd0b19afc3f0 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Octenoic acid 40V, Positive-QTOF | splash10-0a4i-9000000000-45f40a1dbaae13a04dae | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Octenoic acid 10V, Negative-QTOF | splash10-00dl-0900000000-e92c8d4ba859e2c18a1a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Octenoic acid 20V, Negative-QTOF | splash10-0596-0900000000-15af8a5dc0356cd2f4b0 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Octenoic acid 40V, Negative-QTOF | splash10-00kf-9000000000-5f0acc9c148a535551fd | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | 2012-12-04 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
| Show more...
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Biological Properties |
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Cellular Locations | - Extracellular
- Membrane (predicted from logP)
- Microsomes
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Biospecimen Locations | Not Available |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022010 |
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KNApSAcK ID | C00031683 |
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Chemspider ID | 4445840 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | 4146 |
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PubChem Compound | 5282713 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1621221 |
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References |
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Synthesis Reference | Dupont, Georges; Dulou, Raymond; Pigerol, Charles. Kharasch reactions with 1-heptene. Synthesis of octanoic and 2-octenoic acid. Compt. rend. (1955), 240 628-9. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
- Watanabe K, Matsunaga T, Narimatsu S, Yamamoto I, Yoshimura H: Mouse hepatic microsomal oxidation of aliphatic aldehydes (C8 to C11) to carboxylic acids. Biochem Biophys Res Commun. 1992 Oct 15;188(1):114-9. [PubMed:1417834 ]
- Libert R, Draye JP, Van Hoof F, Schanck A, Soumillion JP, de Hoffmann E: Study of reactions induced by hydroxylamine treatment of esters of organic acids and of 3-ketoacids: application to the study of urines from patients under valproate therapy. Biol Mass Spectrom. 1991 Feb;20(2):75-86. [PubMed:1883862 ]
- Yanagisawa I, Yamane M, Urayama T: Simultaneous separation and sensitive determination of free fatty acids in blood plasma by high-performance liquid chromatography. J Chromatogr. 1985 Dec 13;345(2):229-40. [PubMed:4086594 ]
- Tsuchiya H, Hayashi T, Sato M, Tatsumi M, Takagi N: Simultaneous separation and sensitive determination of free fatty acids in blood plasma by high-performance liquid chromatography. J Chromatogr. 1984 Jul 13;309(1):43-52. [PubMed:6480773 ]
- Farine JP, Sirugue D, Abed-Vieillard D, Everaerts C, Le Quere JL, Bonnard O, Brossut R: The male abdominal glands of Leucophaea maderae: chemical identification of the volatile secretion and sex pheromone function. J Chem Ecol. 2007 Feb;33(2):405-15. doi: 10.1007/s10886-006-9224-7. Epub 2007 Jan 3. [PubMed:17200891 ]
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