Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:09:08 UTC |
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Update date | 2019-11-26 03:03:38 UTC |
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Primary ID | FDB010452 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Verbenone |
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Description | Verbenone, also known as verbenone, (1r)-isomer, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Verbenone is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Verbenone is a camphor, celery, and menthol tasting compound and can be found in a number of food items such as spearmint, cabbage, white cabbage, and rosemary, which makes verbenone a potential biomarker for the consumption of these food products. Verbenone is a natural organic compound classified as a terpene that is found naturally in a variety of plants. The chemical has a pleasant characteristic odor. Besides being a natural constituent of plants, it and its analogs are insect pheromones. In particular, verbenone when formulated in a long-lasting matrix has an important role in the control of bark beetles such as the mountain pine beetle and the Southern pine bark beetle . |
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CAS Number | 80-57-9 |
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Structure | |
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Synonyms | Synonym | Source |
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Verbenone, (1S)-isomer | MeSH | Verbenone, (1R)-isomer | MeSH | Verbenone, (+-)-isomer | MeSH | 4,6,6-Trimethylbicyclo(3.1.1)hept-3-en-2-one | biospider | 4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one | biospider | Berbenone | biospider | Bicyclo(3.1.1)hept-3-en-2-one, 4,6,6-trimethyl- | biospider |
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Predicted Properties | |
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Chemical Formula | C10H14O |
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IUPAC name | 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one |
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InChI Identifier | InChI=1S/C10H14O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-8H,5H2,1-3H3 |
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InChI Key | DCSCXTJOXBUFGB-UHFFFAOYSA-N |
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Isomeric SMILES | CC1=CC(=O)C2CC1C2(C)C |
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Average Molecular Weight | 150.2176 |
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Monoisotopic Molecular Weight | 150.10446507 |
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Classification |
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Description | Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Monoterpenoids |
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Direct Parent | Bicyclic monoterpenoids |
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Alternative Parents | |
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Substituents | - Pinane monoterpenoid
- Bicyclic monoterpenoid
- Cyclohexenone
- Ketone
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic 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 | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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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 | 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 | (+)-Verbenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0udr-0900000000-74d7cdf61a27f36cc793 | Spectrum | Predicted GC-MS | (+)-Verbenone, 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 | splash10-0udi-0900000000-73cc0326df372fb217b6 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0900000000-b31e97d57bafe1f0ebb2 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001i-0900000000-572f0defccd5e16ae199 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-bb5c6c299b2cd06f0917 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0900000000-bb5c6c299b2cd06f0917 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000t-0900000000-c80bd5d0d70b884689ae | 2016-08-03 | 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 | C09913 |
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Pubchem Compound ID | 65724 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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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 | Not Available |
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EAFUS ID | 3844 |
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Dr. Duke ID | VERBENONE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00003067 |
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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 | rw1028081 |
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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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allelochemic | | | DUKE | coleopterifuge | 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 | 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 | 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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camphor |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| menthol |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| celery |
- 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.
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