Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:09 UTC |
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Update date | 2020-09-17 15:35:07 UTC |
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Primary ID | FDB012392 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 1-Methoxy-4-(2-propenyl)benzene |
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Description | Estragole or 1-Methoxy-4-(2-propenyl) benzene, also known as methylchavicol, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. Its chemical structure consists of a benzene ring substituted with a methoxy group and an allyl group. It is a colorless liquid, although impure samples can appear yellow. Estragole is a sweet, alcohol, and anise tasting compound. It is used in the preparation of fragrances. Estragole has also been found as a component of various trees and plants, including turpentine (pine oil), anise, fennel, bay, tarragon, and basil. It has also been found in lower concentrations in star anises, hyssops, and tarragons. Estragole has also been detected, but not quantified, in several different foods, such as ceylon cinnamons, dills, sweet bay, gingers, and pepper (spice). |
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CAS Number | 140-67-0 |
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Structure | |
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Synonyms | Synonym | Source |
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Methylchavicol | Kegg | 4-Allylanisole | MeSH | Methyl chavicol | MeSH | p-Allylanisole | MeSH | 1-Allyl-4-methoxybenzene | HMDB | 1-Methoxy-4-(2-propen-1-yl)-benzene | HMDB | 1-Methoxy-4-(2-propen-1-yl)benzene | HMDB | 1-Methoxy-4-(2-propenyl)-benzene | HMDB | 1-Methoxy-4-(2-propenyl)benzene, 9ci | HMDB | 1-Methoxy-4-prop-2-enylbenzene | HMDB | 3-(p-Methoxyphenyl)propene | HMDB | 4-Allyl-1-methoxybenzene | HMDB | 4-Allylmethoxybenzene | HMDB | 4-Methoxyallylbenzene | HMDB | Benzene, 1-methoxy, 4-prop-2-enyl | HMDB | BENZENE,1-allyl,4-methoxy methylchavicol | HMDB | Chavicol methyl ether | HMDB | Chavicyl methyl ether | HMDB | Esdragol | HMDB | Esdragole | HMDB | Esdragon | HMDB | Estragol | HMDB | Estragol (methylchavicol) | HMDB | Estragole | HMDB | Ether, P-allylphenyl methyl | HMDB | FEMA 2411 | HMDB | Isoanethole | HMDB | Isoanthethole | HMDB | Methyl chavicole | HMDB | Methyl chavicole (estragole) | HMDB | Methyl-chavicol | HMDB | O-Methyl-chavicol | HMDB | P-Allyl-anisole | HMDB | P-Allylmethoxybenzene | HMDB | p-Allylphenyl methyl ether | HMDB | p-Methoxyallylbenzene | HMDB | Para-allylanisole (estragole) | HMDB | Tarragon | HMDB | Terragon | HMDB | 1-Methoxy-4-(2-propenyl)benzene | KEGG | 3-(4-Methoxyphenyl)-1-propene | PhytoBank | 3-(4-Methoxyphenyl)propene | PhytoBank | 3-(p-Methoxyphenyl)-1-propene | PhytoBank | Esteragol | PhytoBank | Estragenole | PhytoBank | O-Methylchavicol | PhytoBank | 1-Methoxy-4-(2-propenyl)benzene, 9CI | db_source | 1-methoxy-4-prop-2-enylbenzene | biospider | Allylphenyl methyl ether, p- | biospider | Anisole, p-allyl- | biospider | Benzene, 1-methoxy-4-(2-propen-1-yl)- | biospider | Benzene, 1-methoxy-4-(2-propenyl)- | biospider | p-Allylmethoxybenzene | biospider |
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Predicted Properties | |
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Chemical Formula | C10H12O |
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IUPAC name | 1-methoxy-4-(prop-2-en-1-yl)benzene |
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InChI Identifier | InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3,5-8H,1,4H2,2H3 |
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InChI Key | ZFMSMUAANRJZFM-UHFFFAOYSA-N |
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Isomeric SMILES | COC1=CC=C(CC=C)C=C1 |
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Average Molecular Weight | 148.2017 |
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Monoisotopic Molecular Weight | 148.088815006 |
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Classification |
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Description | Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Phenol ethers |
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Sub Class | Anisoles |
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Direct Parent | Anisoles |
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Alternative Parents | |
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Substituents | - Phenoxy compound
- Methoxybenzene
- Anisole
- Alkyl aryl ether
- Monocyclic benzene moiety
- 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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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: Biological role: |
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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 | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 81.04%; H 8.16%; O 10.80% | DFC |
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Melting Point | Not Available | |
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Boiling Point | Bp16 102° | DFC |
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Experimental Water Solubility | 0.178 mg/mL at 25 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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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 | d15 0.98 | DFC |
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Refractive Index | n27D 1.5230 | 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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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0002-6900000000-67d45b594760b36935df | 2015-03-01 | View Spectrum | GC-MS | 1-Methoxy-4-(2-propenyl)benzene, non-derivatized, GC-MS Spectrum | splash10-0002-6900000000-8e0b04a96054353ba4d2 | Spectrum | GC-MS | 1-Methoxy-4-(2-propenyl)benzene, non-derivatized, GC-MS Spectrum | splash10-0002-5900000000-926e28a4944e333f20a8 | Spectrum | GC-MS | 1-Methoxy-4-(2-propenyl)benzene, non-derivatized, GC-MS Spectrum | splash10-0002-3900000000-fcf899888322560675f8 | Spectrum | GC-MS | 1-Methoxy-4-(2-propenyl)benzene, non-derivatized, GC-MS Spectrum | splash10-0002-6900000000-8e0b04a96054353ba4d2 | Spectrum | GC-MS | 1-Methoxy-4-(2-propenyl)benzene, non-derivatized, GC-MS Spectrum | splash10-0002-5900000000-926e28a4944e333f20a8 | Spectrum | GC-MS | 1-Methoxy-4-(2-propenyl)benzene, non-derivatized, GC-MS Spectrum | splash10-0002-3900000000-fcf899888322560675f8 | Spectrum | Predicted GC-MS | 1-Methoxy-4-(2-propenyl)benzene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-05cs-3900000000-15f67266c369bb73d449 | Spectrum | Predicted GC-MS | 1-Methoxy-4-(2-propenyl)benzene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 1-Methoxy-4-(2-propenyl)benzene, 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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MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-03di-9300000000-ed4cfbbd9e08d2cee0ad | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0002-0900000000-3765ce70f44412b9c202 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-014i-0900000000-e86d0a9f461d702ad87d | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0900000000-6115b055d0ac87df694e | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-2900000000-8be4c2f5dd1b59c563a8 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0uyl-9800000000-da4984de313826c7d325 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-590e344336c3b35d9738 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0900000000-85e1e245e010ba27ce2a | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-3900000000-c9c3734a65e1844d7276 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00dj-1900000000-3370bab5911072db0adf | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00dm-5900000000-2c944ec1b9ce38d95a4e | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004i-9100000000-23d4baf27aa3941828a2 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-c2f74e33d816bec66aa0 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0900000000-7512c83d9a8de7a2b2bb | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a59-2900000000-fe719bda7b98ff0571f7 | 2021-09-24 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 13850247 |
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ChEMBL ID | CHEMBL470671 |
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KEGG Compound ID | C10452 |
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Pubchem Compound ID | 8815 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 649 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB34121 |
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CRC / DFC (Dictionary of Food Compounds) ID | HGQ74-N:HGS47-R |
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EAFUS ID | 1117 |
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Dr. Duke ID | CHAVICOL-METHYL-ETHER|METHYL-CHAVICOL|ESTRAGOLE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002740 |
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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 | 140-67-0 |
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GoodScent ID | rw1013251 |
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SuperScent ID | 8815 |
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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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anti aggregant | | | DUKE | calcium antagonist | 48706 | Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances. | DUKE | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | carcinogenic | 50903 | A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities. | DUKE | DNA-binder | | | DUKE | flavor | 48318 | A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. | DUKE | hepatocarcinogenic | 50903 | A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities. | DUKE | hypothermic | | | DUKE | insecticide | 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 | insectifuge | 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 | mutagenic | | | 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 |
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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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licorice |
- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
| anise |
- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| sweet |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| vanilla |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| alcohol |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| minty |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| sassafrass |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| spice |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| green |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| herbal |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| fennel |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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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. — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
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