Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:15:46 UTC |
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Update date | 2019-11-26 03:20:31 UTC |
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Primary ID | FDB021536 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Methylisoeugenol |
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Description | Methylisoeugenol belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups. Methylisoeugenol is a mild, bitter, and clove tasting compound. Methylisoeugenol is found, on average, in the highest concentration within a few different foods, such as nutmegs (Myristica fragrans), star anises (Illicium verum), and gingers (Zingiber officinale). Methylisoeugenol has also been detected, but not quantified in, several different foods, such as wild carrots (Daucus carota), carrots (Daucus carota ssp. sativus), sweet basils (Ocimum basilicum), tarragons (Artemisia dracunculus), and evergreen blackberries (Rubus laciniatus). This could make methylisoeugenol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Methylisoeugenol. |
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CAS Number | 6379-72-2 |
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Structure | |
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Synonyms | Synonym | Source |
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(Z)-Methyl isoeugenol | ChEBI | cis-4-Propenyl veratrole | ChEBI | cis-Methyl isoeugenol | ChEBI | (e)-Methyl eugenol | HMDB | (e)-Methyl isoeugenol | HMDB | 1,2-Dimethoxy-4-(1-propenyl)benzene, 9ci | HMDB | 1,2-Dimethoxy-4-propenyl-(e)-benzene | HMDB | 1,2-Dimethoxy-4-propenyl-benzene | HMDB | 1,2-Dimethoxy-4-propenylbenzene | HMDB | 1,3,4-Isoeugenol methyl ether | HMDB | 1-(3,4-Dimethoxyphenyl)-1-propene | HMDB | 1-Veratryl-1-propene | HMDB | 3,4-Dimethoxypropenylbenzene | HMDB | 4-(1-Propenyl)veratrole | HMDB | 4-Propenyl-1,2-dimethoxybenzene | HMDB | 4-Propenylveratrole | HMDB | 4-trans-Propenylveratrole | HMDB | FEMA 2476 | HMDB | Isoeugenol methyl ether | HMDB | Isoeugenyl methyl ether | HMDB | Isohomogenol | HMDB | Isomethyleugenol | HMDB, MeSH | Methyl isoeugenol | HMDB, MeSH | O-Methylisoeugenol | HMDB | trans-4-Propenylveratrole | HMDB | trans-Isomethyleugenol | HMDB, MeSH | trans-Methyl isoeugenol | HMDB | 1,2-Dimethoxy-4-(1-e-propenyl)benzene | MeSH, HMDB | 1,2-Dimethoxy-4-(1-propenyl)benzene | MeSH, HMDB | 1,2-Dimethoxy-4-(1-Z-propenyl)benzene | MeSH, HMDB | Isomethyleugenol, (e)-isomer | MeSH, HMDB | Isomethyleugenol, (Z)-isomer | MeSH, HMDB | Methylisoeugenol | MeSH | (e)-methyl eugenol | biospider | (e)-methyl isoeugenol | biospider | 1,2-Dimethoxy-4-(1-propenyl)benzene, 9CI | db_source | Benzene, 1,2-dimethoxy-4-propenyl- | biospider | Benzene, 1,2-dimethoxy-4-propenyl-, (E)- | biospider | O-methylisoeugenol | biospider | Trans-isomethyleugenol | biospider | Trans-methyl isoeugenol | biospider |
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Predicted Properties | |
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Chemical Formula | C11H14O2 |
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IUPAC name | 1,2-dimethoxy-4-[(1Z)-prop-1-en-1-yl]benzene |
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InChI Identifier | InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4-8H,1-3H3/b5-4- |
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InChI Key | NNWHUJCUHAELCL-PLNGDYQASA-N |
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Isomeric SMILES | COC1=C(OC)C=C(\C=C/C)C=C1 |
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Average Molecular Weight | 178.2277 |
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Monoisotopic Molecular Weight | 178.099379692 |
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Classification |
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Description | Belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups. |
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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 | Methoxybenzenes |
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Direct Parent | Dimethoxybenzenes |
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Alternative Parents | |
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Substituents | - O-dimethoxybenzene
- Dimethoxybenzene
- Phenoxy compound
- Styrene
- Phenol ether
- Anisole
- Alkyl aryl ether
- Ether
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Liquid | |
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Physical Description | Not Available | |
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Mass Composition | C 74.13%; H 7.92%; O 17.95% | DFC |
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Melting Point | Mp 16-17° | DFC |
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Boiling Point | Bp12 138-140° | DFC |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | n20D 1.5616 | DFC |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | (Z)-Methyl isoeugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-03fs-1900000000-3d41a0d29a7363963fbb | Spectrum | Predicted GC-MS | (Z)-Methyl isoeugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0900000000-1b4a5c893c8cb3d52797 | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-2900000000-dd43f9e1c8e86b7ba6ff | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9500000000-20fd1ba2b53cc59be2ea | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0900000000-13d0af68ffab1cb5c56d | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-0900000000-02afbb666cbaaa0c075e | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-07cr-4900000000-6a705aba56bdf50c3728 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0900000000-cde372377d8e900ad3a3 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0fb9-0900000000-28cc89aae8d7b76189de | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004i-9400000000-219c0ddce8933e6a09c3 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0900000000-583273c8100f9e55b4bd | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004j-0900000000-75e41d1bbbb423dac95f | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-02u9-9800000000-aa3ed6a53e37b0107f0e | 2021-09-22 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 21242881 |
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ChEMBL ID | CHEMBL1164609 |
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KEGG Compound ID | C10478 |
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Pubchem Compound ID | 1549045 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 6877 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB41553 |
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CRC / DFC (Dictionary of Food Compounds) ID | MVN84-F:NZP08-I |
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EAFUS ID | 1891 |
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Dr. Duke ID | METHYL-ISOEUGENOL|(E)-METHYL-ISOEUGENOL|ISOEUGENOL-METHYL-ETHER|TRANS-METHYL-ISOEUGENOL |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002760 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | rw1435071 |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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anesthetic | | | DUKE | anti aggregant | | | DUKE | anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | anti histaminic | 37956 | Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists. | DUKE | anti spasmodic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | candidicide | | | DUKE | expectorant | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | flavor | 48318 | A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. | DUKE | herbicide | 24527 | A substance used to destroy plant pests. | DUKE | insect attractant | 24852 | Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects. | DUKE | nematicide | 25491 | A substance used to destroy pests of the phylum Nematoda (roundworms). | DUKE | perfumery | 48318 | A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | toxic | 52209 | A role played by the molecular entity or part thereof which causes the development of a pathological process. | DUKE |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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mild |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| spicy |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| clove |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| bitter |
- Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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