Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 17:50:48 UTC |
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Update Date | 2023-02-21 17:22:30 UTC |
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HMDB ID | HMDB0032617 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Methyl phenylacetate |
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Description | Methyl phenylacetate, also known as fema 2733 or mephaneine, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Methyl phenylacetate is a sweet, almond, and floral tasting compound. Methyl phenylacetate is found, on average, in the highest concentration within corns. Methyl phenylacetate has also been detected, but not quantified, in several different foods, such as cocoa and cocoa products, coffee and coffee products, fruits, and pepper (c. frutescens). This could make methyl phenylacetate a potential biomarker for the consumption of these foods. Methyl phenylacetate has a strong odor similar to honey. It is a colorless liquid that is only slightly soluble in water, but soluble in most organic solvents. It is used in the flavor industry and in perfumes to impart honey scents. This compound also occurs in brandy, capsicum, coffee, honey, pepper, and some wine. Methyl phenyldiazoacetate, precursor to cyclopropanation agents, is prepared by treating methyl phenylacetate with p-acetamidobenzenesulfonyl azide in the presence of base. Methyl phenylacetate is an organic compound that is the methyl ester of phenylacetic acid, with the structural formula C6H5CH2COOCH3. |
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Structure | InChI=1S/C9H10O2/c1-11-9(10)7-8-5-3-2-4-6-8/h2-6H,7H2,1H3 |
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Synonyms | Value | Source |
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Methyl phenylacetic acid | Generator | FEMA 2733 | HMDB | Mephaneine | HMDB | Methyl alpha-toluate | HMDB | Methyl ester OF phenylacetic acid | HMDB | Methyl 2-phenylacetic acid | Generator | Methyl phenylacetate | MeSH |
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Chemical Formula | C9H10O2 |
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Average Molecular Weight | 150.1745 |
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Monoisotopic Molecular Weight | 150.068079564 |
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IUPAC Name | methyl 2-phenylacetate |
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Traditional Name | methyl phenylacetate |
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CAS Registry Number | 101-41-7 |
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SMILES | COC(=O)CC1=CC=CC=C1 |
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InChI Identifier | InChI=1S/C9H10O2/c1-11-9(10)7-8-5-3-2-4-6-8/h2-6H,7H2,1H3 |
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InChI Key | CRZQGDNQQAALAY-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Not Available |
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Direct Parent | Benzene and substituted derivatives |
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Alternative Parents | |
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Substituents | - Monocyclic benzene moiety
- Methyl ester
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Not Available |
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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 IndicesUnderivatized |
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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 - Methyl phenylacetate EI-B (Non-derivatized) | splash10-0006-9200000000-389b3d6431858f4110c9 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Methyl phenylacetate EI-B (Non-derivatized) | splash10-0006-9200000000-eeeabb5445489ab0953b | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Methyl phenylacetate EI-B (Non-derivatized) | splash10-0006-9100000000-18e224838518b1ddae9f | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Methyl phenylacetate EI-B (Non-derivatized) | splash10-0006-9100000000-1edd67a79f223f827641 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Methyl phenylacetate EI-B (Non-derivatized) | splash10-0006-9200000000-389b3d6431858f4110c9 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Methyl phenylacetate EI-B (Non-derivatized) | splash10-0006-9200000000-eeeabb5445489ab0953b | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Methyl phenylacetate EI-B (Non-derivatized) | splash10-0006-9100000000-18e224838518b1ddae9f | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Methyl phenylacetate EI-B (Non-derivatized) | splash10-0006-9100000000-1edd67a79f223f827641 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Methyl phenylacetate GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9200000000-87bae92e5b97546941aa | 2016-09-22 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Methyl phenylacetate GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0006-9200000000-52232f96c18eca1b2394 | 2015-03-01 | 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 - Methyl phenylacetate 10V, Positive-QTOF | splash10-0gb9-0900000000-f25a76df13db20a2b410 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methyl phenylacetate 20V, Positive-QTOF | splash10-0gbc-3900000000-511b0f2135ac341e4b05 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methyl phenylacetate 40V, Positive-QTOF | splash10-0006-9300000000-137ed2396b7316ce0579 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methyl phenylacetate 10V, Negative-QTOF | splash10-0002-0900000000-f12b2444ec831bdb6ca9 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methyl phenylacetate 20V, Negative-QTOF | splash10-00kb-0900000000-714e146d401300f08a2c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methyl phenylacetate 40V, Negative-QTOF | splash10-014i-4900000000-d72c1c0fc3949b615eb9 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methyl phenylacetate 10V, Negative-QTOF | splash10-0007-9800000000-5ae7754141b3f8f634c0 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methyl phenylacetate 20V, Negative-QTOF | splash10-00kf-9500000000-09614850d98f667a51b7 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methyl phenylacetate 40V, Negative-QTOF | splash10-0006-9000000000-ee5158f79753ba716d14 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methyl phenylacetate 10V, Positive-QTOF | splash10-0006-9600000000-ab903e003c3368a3914e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methyl phenylacetate 20V, Positive-QTOF | splash10-0006-9000000000-d017d7725bdee26883d1 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methyl phenylacetate 40V, Positive-QTOF | splash10-0006-9000000000-5190dde93ea85ed050ff | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-04 | FELIX lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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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 | FDB010559 |
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KNApSAcK ID | C00051576 |
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Chemspider ID | 7278 |
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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 | Methyl phenylacetate |
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METLIN ID | Not Available |
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PubChem Compound | 7559 |
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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 | rw1008431 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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