Record Information |
---|
Version | 1.0 |
---|
Creation date | 2010-04-08 22:10:09 UTC |
---|
Update date | 2020-09-17 15:35:07 UTC |
---|
Primary ID | FDB012392 |
---|
Secondary Accession Numbers | Not Available |
---|
Chemical Information |
---|
FooDB Name | 1-Methoxy-4-(2-propenyl)benzene |
---|
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). |
---|
CAS Number | 140-67-0 |
---|
Structure | |
---|
Synonyms | Synonym | Source |
---|
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 |
|
---|
Predicted Properties | |
---|
Chemical Formula | C10H12O |
---|
IUPAC name | 1-methoxy-4-(prop-2-en-1-yl)benzene |
---|
InChI Identifier | InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3,5-8H,1,4H2,2H3 |
---|
InChI Key | ZFMSMUAANRJZFM-UHFFFAOYSA-N |
---|
Isomeric SMILES | COC1=CC=C(CC=C)C=C1 |
---|
Average Molecular Weight | 148.2017 |
---|
Monoisotopic Molecular Weight | 148.088815006 |
---|
Classification |
---|
Description | Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. |
---|
Kingdom | Organic compounds |
---|
Super Class | Benzenoids |
---|
Class | Phenol ethers |
---|
Sub Class | Anisoles |
---|
Direct Parent | Anisoles |
---|
Alternative Parents | |
---|
Substituents | - Phenoxy compound
- Methoxybenzene
- Anisole
- Alkyl aryl ether
- Monocyclic benzene moiety
- Ether
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic homomonocyclic compound
|
---|
Molecular Framework | Aromatic homomonocyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Disposition | Route of exposure: Source: Biological location: |
---|
Role | Industrial application: Biological role: |
---|
Physico-Chemical Properties |
---|
Physico-Chemical Properties - Experimental | Property | Value | Reference |
---|
Physical state | Not Available | |
---|
Physical Description | Not Available | |
---|
Mass Composition | C 81.04%; H 8.16%; O 10.80% | DFC |
---|
Melting Point | Not Available | |
---|
Boiling Point | Bp16 102° | DFC |
---|
Experimental Water Solubility | 0.178 mg/mL at 25 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
---|
Experimental logP | Not Available | |
---|
Experimental pKa | Not Available | |
---|
Isoelectric point | Not Available | |
---|
Charge | Not Available | |
---|
Optical Rotation | Not Available | |
---|
Spectroscopic UV Data | Not Available | |
---|
Density | d15 0.98 | DFC |
---|
Refractive Index | n27D 1.5230 | DFC |
---|
|
---|
Spectra |
---|
Spectra | |
---|
EI-MS/GC-MS | Type | Description | Splash Key | View |
---|
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 |
|
---|
MS/MS | Type | Description | Splash Key | View |
---|
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 |
|
---|
NMR | Type | Description | | View |
---|
1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental) | | Spectrum |
|
---|
External Links |
---|
ChemSpider ID | 13850247 |
---|
ChEMBL ID | CHEMBL470671 |
---|
KEGG Compound ID | C10452 |
---|
Pubchem Compound ID | 8815 |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | Not Available |
---|
Phenol-Explorer ID | 649 |
---|
DrugBank ID | Not Available |
---|
HMDB ID | HMDB34121 |
---|
CRC / DFC (Dictionary of Food Compounds) ID | HGQ74-N:HGS47-R |
---|
EAFUS ID | 1117 |
---|
Dr. Duke ID | CHAVICOL-METHYL-ETHER|METHYL-CHAVICOL|ESTRAGOLE |
---|
BIGG ID | Not Available |
---|
KNApSAcK ID | C00002740 |
---|
HET ID | Not Available |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
Flavornet ID | 140-67-0 |
---|
GoodScent ID | rw1013251 |
---|
SuperScent ID | 8815 |
---|
Wikipedia ID | Not Available |
---|
Phenol-Explorer Metabolite ID | Not Available |
---|
Duplicate IDS | Not Available |
---|
Old DFC IDS | Not Available |
---|
Associated Foods |
---|
Food | Content Range | Average | Reference |
---|
Food | | | Reference |
---|
|
Biological Effects and Interactions |
---|
Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
---|
Anti-aggregant | | An agent that prevents platelet aggregation, reducing blood clot formation. Its biological role is to inhibit platelet activation, and its therapeutic applications include preventing thrombosis and stroke. Key medical uses include treating cardiovascular diseases, such as myocardial infarction and atrial fibrillation, and managing conditions that increase the risk of blood clots. | DUKE | Calcium antagonist | 48706 | A medication that blocks calcium ion entry into cells, reducing muscle contraction and vascular resistance. It treats hypertension, angina, and arrhythmias by dilating blood vessels and decreasing cardiac workload, commonly used in managing cardiovascular diseases. | DUKE | Cancer preventive | 35610 | An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence. | DUKE | Carcinogenic | 50903 | An agent that causes cancer, damaging cellular DNA and disrupting normal cell growth. It has no therapeutic applications, but understanding its biological role informs cancer prevention and treatment strategies, with key medical uses in oncology research and risk assessment. | DUKE | DNA-binder | | An agent that binds to DNA, regulating gene expression and replication. It has therapeutic applications in gene therapy, cancer treatment, and antimicrobial therapy, with key medical uses including targeting viral DNA and modulating immune responses. | DUKE | Name | 48318 | flavor | DUKE | Hepatocarcinogenic | 50903 | An agent that promotes the development of liver cancer, having a harmful biological role. It has no therapeutic applications, but understanding its effects is crucial in liver cancer research and prevention. Key medical uses include studying liver carcinogenesis and developing strategies to mitigate its harmful effects. | DUKE | Hypothermic | | A condition of abnormally low body temperature, playing a biological role in reducing metabolic rate and oxygen demand. Therapeutically, it has applications in neuroprotection, cardiac surgery, and trauma care. Key medical uses include treating heatstroke, cardiac arrest, and brain injuries, as well as preserving organs for transplantation. | DUKE | Insecticide | 24852 | An agent that kills or repels insects, used to control pests and prevent disease transmission. Therapeutically, insecticides have applications in public health and veterinary medicine, key medical uses include controlling insect-borne diseases such as malaria, typhus, and Lyme disease. | DUKE | Insectifuge | 24852 | A substance that repels insects, playing a biological role in plant defense. Therapeutically, it has applications in preventing insect-borne diseases. Key medical uses include topical repellents for malaria, dengue fever, and other vector-borne illnesses, reducing the risk of transmission. | DUKE | Mutagenic | | An agent that induces genetic mutations, altering DNA sequences. It plays a biological role in evolution and adaptation. Therapeutically, mutagenic agents are used in cancer treatment, such as chemotherapy, and in gene therapy to introduce beneficial traits. Key medical uses include oncology and genetic research. | DUKE | Perfumery | 48318 | The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties. | DUKE | Pesticide | 25944 | An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections. | DUKE |
|
---|
Enzymes | Not Available |
---|
Pathways | Not Available |
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Flavor | Citations |
---|
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.
|
|
---|
Files |
---|
MSDS | Not Available |
---|
References |
---|
Synthesis Reference | Not Available |
---|
General Reference | Not Available |
---|
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.
|
---|