| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:05:31 UTC |
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| Update date | 2020-09-17 15:36:19 UTC |
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| Primary ID | FDB002793 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Anethole |
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| Description | Anethole or 1-Methoxy-4(1-propenyl)-benzene, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. Anethole is an extremely weak basic (essentially neutral) compound (based on its pKa). Anethol is a naturally occurring organic compound found in the essential oils of many plants such as anise, fennel, anise myrtle, liquorice as their large component of the odor and flavor. Anethole is a sweet, anise, and balsam tasting compound. It is used as a flavoring agent in alcoholic drinks and in small quantities in natural berry flavors. Anethole is found in a lower concentration in peppermints, wild celeries, and corianders. Anethole has also been detected, but not quantified in, several different foods, such as nutmegs, cumins, lemon balms, common thymes, and herbs and spices. This could make anethole a potential biomarker for the consumption of these foods. Anethole has potent antimicrobial, nematicidal and antifungal activities (PMID:11807977, 17078111, 18944489). There are two known anethol isomers including Cis- and Trans-anethol. |
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| CAS Number | 4180-23-8 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Not Available | Not Available |
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| Predicted Properties | |
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| Chemical Formula | C10H12O |
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| IUPAC name | 1-methoxy-4-[(1Z)-prop-1-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/h3-8H,1-2H3/b4-3- |
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| InChI Key | RUVINXPYWBROJD-ARJAWSKDSA-N |
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| Isomeric SMILES | COC1=CC=C(\C=C/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
- Styrene
- 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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| Physico-Chemical Properties |
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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 81.04%; H 8.16%; O 10.80% | DFC |
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| Melting Point | Mp 22.5° | DFC |
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| Boiling Point | Bp 235° | 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 | [neutral] lmax 259 (e 22300) (MeOH) (Berdy) | DFC |
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| Density | Not Available | |
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| Refractive Index | Not Available | |
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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 | Anethole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-000t-2900000000-0665985a70ac9c27eb53 | Spectrum | | Predicted GC-MS | Anethole, 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 | splash10-0002-0900000000-436711faeb648ff2a2d5 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-2900000000-7d9dfbe23492f9be6a29 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fr6-9600000000-582716ef7e52a802bbc1 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-e66c5cd440af8e6d0c88 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0900000000-709cb24546c67c386dde | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-3900000000-ecda3d7970e587876f66 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-c2f74e33d816bec66aa0 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0900000000-5aa2093882ee9ccdc886 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-053r-3900000000-03b30da0f9adb9d580ff | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0900000000-d856cd34f2f6f83def66 | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00dj-2900000000-b32a050861e7a927efa5 | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004i-9100000000-e059cbeab65dc16bd3b4 | 2021-09-23 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | Not Available |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | Not Available |
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| Pubchem Compound ID | 637563 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | 35616 |
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| Phenol-Explorer ID | 645 |
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| DrugBank ID | Not Available |
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| HMDB ID | Not Available |
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| CRC / DFC (Dictionary of Food Compounds) ID | HBT07-B:CNR12-S |
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| EAFUS ID | 213 |
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| Dr. Duke ID | ANETHOL|ANETHOLE|TRANS-ANETHOLE |
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| BIGG ID | Not Available |
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| KNApSAcK ID | C00029334 |
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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 | rw1001151 |
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| SuperScent ID | 637563 |
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| Wikipedia ID | Not Available |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | |
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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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| allergenic | 50904 | A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy. | DUKE | | analgesic | 35480 | An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms. | DUKE | | anesthetic | | | DUKE | | anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | | anti genotoxic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti hepatotic | 62868 | Any compound that is able to prevent damage to the liver. | DUKE | | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | | anti NF-kappa-B | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | | antioxidant | 22586 | A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. | DUKE | | anti radicular | | | DUKE | | anti salmonella | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | | anti septic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | | anti spasmodic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti TNF | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | | antitumor | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti yeast | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | 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 | | candidicide | | | DUKE | | carminative | | | DUKE | | dermatitigenic | | | DUKE | | digestive | | | DUKE | | estrogenic | | | 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 | | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | | gastrostimulant | 55324 | A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion. | DUKE | | hepatotoxic | 50908 | A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals. | DUKE | | immunostimulant | 50847 | A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity. | 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 | | irritant | | | DUKE | | lactagogue | | | DUKE | | leucocytogenic | | | DUKE | | mutagenic | | | DUKE | | nephroprotective | 76595 | Any protective agent that is able to prevent damage to the kidney. | 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 | | secretogogue | | | DUKE | | secretolytic | | | DUKE | | sweetener | 50505 | Substance that sweeten food, beverages, medications, etc. | DUKE | | sympathomimetic | 35524 | A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters. | 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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| anise |
- 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.
| | balsam |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| | sweet |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| | licorice |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| | mimosa |
- 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).
— 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.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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