Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2021-09-24 09:49:03 UTC |
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Update Date | 2021-09-24 09:49:03 UTC |
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HMDB ID | HMDB0304443 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | octanoate |
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Description | Caprylic acid, or octanoic acid, with the structural formula CH3(CH2)6CO2H, is an eight-carbon straight-chain fatty acid and a carboxylic acid. It is an oily Liquid with a slightly unpleasant rancid taste and odor. It is minimally soluble in water. Caprylic acid can be found in numerous foods such as Prunus (Cherry, Plum), pineapple sages, black raspberries, shallots, coconuts and breast milk. Caprylic acid is taken as a dietary supplement. Caprylic acid is used commercially in the production of esters used in perfumery and in the manufacture of dyes. Caprylic acid is an antimicrobial pesticide used as a food contact surface sanitizer on dairy equipment, food processing equipment, breweries, wineries, and beverage processing plants. It is also used as disinfectant in health care facilities, schools/colleges, industrial facilities, recreational facilities, retail and wholesale establishments, livestock premises, restaurants, and hotels/motels. In addition, caprylic acid is used as an algicide, bactericide, fungicide, and herbicide in greenhouses and garden centers. Caprylic acid, and other fatty acids, affect the hunger hormone ghrelin. Ghrelin must be acylated, where it acquires an -OH group, before it can stimulate the hunger receptors in the hypothalamus. Caprylic acid becomes linked post-translationally to serine at the 3-position by the enzyme ghrelin O-acyltransferase (GOAT), located on the cell membrane of ghrelin cells in the stomach and pancreas (PMID 19896496 ). Caprylic acid affects those with medium-chain acyl-CoA dehydrogenase deficiency (MCAD), which is an inborn error of metabolism, marked by mutations of the gene ACADM. Those affected with MCAD have difficulties converting fatty acids to energy, especially during fasting. As a result, fatty acids build up and cause damage to liver and brain (PMID: 27536022 ). |
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Structure | InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)/p-1 |
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Synonyms | Value | Source |
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1-Heptanecarboxylate | ChEBI | Caprilate | ChEBI | Caprylate | ChEBI | CH3-[CH2]6-COO(-) | ChEBI | N-Caprylate | ChEBI | N-Octanoate | ChEBI | N-Octoate | ChEBI | N-Octylate | ChEBI | Octanoic acid, ion(1-) | ChEBI | Octylate | ChEBI | 1-Heptanecarboxylic acid | Generator | Caprilic acid | Generator | Caprylic acid | Generator | N-Caprylic acid | Generator | N-Octanoic acid | Generator | N-Octoic acid | Generator | N-Octylic acid | Generator | Octanoate, ion(1-) | Generator | Octylic acid | Generator | Octanoic acid | Generator | Caprylic acid, 14C-labeled | MeSH | Caprylic acid, aluminum salt | MeSH | Caprylic acid, ammonia salt | MeSH | Caprylic acid, barium salt | MeSH | Caprylic acid, cadmium salt | MeSH | Caprylic acid, calcium salt | MeSH | Caprylic acid, cesium salt | MeSH | Caprylic acid, chromium(+2) salt | MeSH | Caprylic acid, cobalt salt | MeSH | Caprylic acid, copper salt | MeSH | Caprylic acid, copper(+2) salt | MeSH | Caprylic acid, iridum(+3) salt | MeSH | Caprylic acid, iron(+3) salt | MeSH | Caprylic acid, lanthanum(+3) salt | MeSH | Caprylic acid, lead(+2) salt | MeSH | Caprylic acid, lithium salt | MeSH | Caprylic acid, manganese salt | MeSH | Caprylic acid, nickel(+2) salt | MeSH | Caprylic acid, potassium salt | MeSH | Caprylic acid, ruthenium(+3) salt | MeSH | Caprylic acid, sodium salt | MeSH | Caprylic acid, sodium salt, 11C-labeled | MeSH | Caprylic acid, tin salt | MeSH | Caprylic acid, tin(+2) salt | MeSH | Caprylic acid, zinc salt | MeSH | Caprylic acid, zirconium salt | MeSH | Caprylic acid, zirconium(+4) salt | MeSH | Lithium octanoate | MeSH | Sodium caprylate | MeSH | Sodium octanoate | MeSH |
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Chemical Formula | C8H15O2 |
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Average Molecular Weight | 143.2035 |
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Monoisotopic Molecular Weight | 143.107204724 |
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IUPAC Name | octanoate |
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Traditional Name | octanoate |
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CAS Registry Number | Not Available |
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SMILES | CCCCCCCC([O-])=O |
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InChI Identifier | InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)/p-1 |
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InChI Key | WWZKQHOCKIZLMA-UHFFFAOYSA-M |
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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
- Straight chain fatty acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Organic anion
- 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 | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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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 IndicesNot Available |
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| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - octanoate 10V, Positive-QTOF | splash10-002f-2900000000-755179c9d14d1bbb77ec | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - octanoate 20V, Positive-QTOF | splash10-002g-9800000000-9285cc5963f767a994c3 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - octanoate 40V, Positive-QTOF | splash10-052f-9000000000-06a4c61d4c63d7897463 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - octanoate 10V, Negative-QTOF | splash10-0006-3900000000-c8005ce6014073d81b47 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - octanoate 20V, Negative-QTOF | splash10-0007-6900000000-f6abffe9512a2dfa8afe | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - octanoate 40V, Negative-QTOF | splash10-0002-9200000000-df94975221001b91f233 | 2016-09-12 | Wishart Lab | View Spectrum |
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