| Record Information |
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| Version | 2.0 |
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| Created at | 2012-09-11 17:46:02 UTC |
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| Updated at | 2024-09-03 04:15:58 UTC |
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| NP-MRD ID | NP0001082 |
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| Natural Product DOI | https://doi.org/10.57994/0477 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Methyleugenol |
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| Description | Methyleugenol, also known as 4-allylveratrole or eugenol methyl, 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. FDA noted the action was despite its continuing stance that this substance does not pose a risk to public health under the conditions of its intended use. Methyleugenol is a sweet, anise, and apricot tasting compound. Methyleugenol is found, on average, in the highest concentration within a few different foods, such as allspices, tarragons, and sweet bay and in a lower concentration in sweet basils, rosemaries, and hyssops. Methyleugenol has also been detected, but not quantified, in several different foods, such as soy beans, evergreen blackberries, muskmelons, citrus, and pomes. This could make methyleugenol a potential biomarker for the consumption of these foods. As of October 2018, the US FDA withdrew authorization for the use of methyl eugenol as a synthetic flavoring substance for use in food because petitioners provided data demonstrating that these additives induce cancer in laboratory animals. Methyleugenol is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Methyl eugenol (allylveratrol) is a natural chemical compound classified as a phenylpropene, a type of phenylpropanoid. It is the methyl ether of eugenol and is important to insect behavior and pollination. Their ability to attract insects, particularly Bactrocera fruit flies was first noticed in 1915 by F. M. Howlett. The compound may have evolved in response to pathogens, as methyl eugenol has some antifungal activity. Methyl eugenol is found in a number of plants (over 450 species from 80 families including both angiosperm and gymnosperm families) and has a role in attracting pollinators. About 350 plant species have them as a component of floral fragrance. |
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| Structure | InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4,6-8H,1,5H2,2-3H3 |
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| Synonyms | | Value | Source |
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| 1,2-Dimethoxy-4-(2-propenyl)benzene | ChEBI | | Eugenol methyl ether | ChEBI | | Methyl eugenol | ChEBI | | O-Methyleugenol | Kegg | | 1, 2-Dimethoxy-4-(2-propenyl)benzene | HMDB | | 1-(3, 4-Dimethoxyphenyl)-2-propene | HMDB | | 4-Allyl-1, 2-dimethoxybenzene | HMDB | | 4-Allyl-1,2-dimethoxy-benzene | HMDB | | 4-Allyl-1,2-dimethyoxybenzene | HMDB | | 4-Allylveratrole | HMDB | | Allyl-1,2-dimethoxybenzene | HMDB | | Benzene, 4-(2-propenyl)-1,2-dimethoxy | HMDB | | Eugenol methyl | HMDB | | FEMA 2475 | HMDB | | Methyleugenol | ChEBI | | 4-Allyl-1,2-dimethoxybenzene | MeSH | | 1-Allyl-3,4-dimethoxybenzene | MeSH | | 1,2-Dimethoxy-4-(2-propen-1-yl)benzene | PhytoBank | | 1,2-Dimethoxy-4-allylbenzene | PhytoBank | | 1,3,4-Eugenol methyl ether | PhytoBank | | 1-(3,4-Dimethoxyphenyl)-2-propene | PhytoBank | | 3,4-Dimethoxy-1-(2-propenyl)benzene | PhytoBank | | 3,4-Dimethoxyallylbenzene | PhytoBank | | 3-(3,4-Dimethoxyphenyl)-1-propene | PhytoBank | | 3-(3,4-Dimethoxyphenyl)propene | PhytoBank | | Chavibetol methyl ether | PhytoBank | | Eugenyl methyl ether | PhytoBank | | Methyl eugenol ether | PhytoBank | | Methyl eugenyl ether | PhytoBank | | Methylchavibetol | PhytoBank | | Veratrole methyl ether | PhytoBank |
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| Chemical Formula | C11H14O2 |
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| Average Mass | 178.2277 Da |
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| Monoisotopic Mass | 178.09938 Da |
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| IUPAC Name | 1,2-dimethoxy-4-(prop-2-en-1-yl)benzene |
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| Traditional Name | methyl eugenol |
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| CAS Registry Number | 93-15-2 |
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| SMILES | COC1=C(OC)C=C(CC=C)C=C1 |
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| InChI Identifier | InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4,6-8H,1,5H2,2-3H3 |
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| InChI Key | ZYEMGPIYFIJGTP-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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| 1D_DEPT NMR | 13C NMR Spectrum (1D, 126 MHz, CDCl3, experimental) | shaolidong@ynutcm.edu.cn | Not Available | Not Available | 2024-05-11 | View Spectrum | | 1D_DEPT NMR | 13C NMR Spectrum (1D, 126 MHz, CDCl3, experimental) | shaolidong@ynutcm.edu.cn | Not Available | Not Available | 2024-05-11 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, CDCl3, experimental) | shaolidong@ynutcm.edu.cn | Not Available | Not Available | 2024-05-11 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental) | shaolidong@ynutcm.edu.cn | Not Available | Not Available | 2024-05-11 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| | 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, 500.33, CDCl3, simulated) | Not Available | Not Available | Not Available | 2024-05-11 | 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 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
- 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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| Physical Properties |
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| State | Liquid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | -4 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 0.5 mg/mL at 25 °C | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| General References | - Yano S, Suzuki Y, Yuzurihara M, Kase Y, Takeda S, Watanabe S, Aburada M, Miyamoto K: Antinociceptive effect of methyleugenol on formalin-induced hyperalgesia in mice. Eur J Pharmacol. 2006 Dec 28;553(1-3):99-103. Epub 2006 Sep 23. [PubMed:17049512 ]
- Xiao WW, Zhang HL, Wang CF, Chen Y, Zhan R, Li D, Shao LD: Chemical Synthesis Enables the Configurational Determination of Myristriol, a Highly Oxygenated Phenylpropanoid from Myristica fragrans Houtt. Chem Biodivers. 2023 Mar;20(3):e202201075. doi: 10.1002/cbdv.202201075. Epub 2023 Feb 20. [PubMed:36762483 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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