Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:42 UTC |
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Update date | 2019-11-26 02:58:38 UTC |
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Primary ID | FDB003216 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 3,5,5-Trimethyl-2-cyclohexen-1-one |
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Description | 3,5,5-Trimethyl-2-cyclohexen-1-one, also known as isoacetophorone or isoforone, belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 3,5,5-Trimethyl-2-cyclohexen-1-one is a sweet, camphor, and camphoraceous tasting compound. 3,5,5-Trimethyl-2-cyclohexen-1-one is found, on average, in the highest concentration within kohlrabis (Brassica oleracea var. gongylodes). 3,5,5-Trimethyl-2-cyclohexen-1-one has also been detected, but not quantified in, several different foods, such as garden tomatoes (Solanum lycopersicum), fruits, saffrons (Crocus sativus), white mustards (Sinapis alba), and garden tomato (var.). This could make 3,5,5-trimethyl-2-cyclohexen-1-one a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 3,5,5-Trimethyl-2-cyclohexen-1-one. |
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CAS Number | 78-59-1 |
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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 | C9H14O |
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IUPAC name | 3,5,5-trimethylcyclohex-2-en-1-one |
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InChI Identifier | InChI=1S/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h4H,5-6H2,1-3H3 |
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InChI Key | HJOVHMDZYOCNQW-UHFFFAOYSA-N |
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Isomeric SMILES | CC1=CC(=O)CC(C)(C)C1 |
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Average Molecular Weight | 138.2069 |
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Monoisotopic Molecular Weight | 138.10446507 |
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Classification |
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Description | Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbonyl compounds |
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Direct Parent | Cyclohexenones |
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Alternative Parents | |
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Substituents | - Cyclohexenone
- Organic oxide
- Hydrocarbon derivative
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic 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: Environmental role: |
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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 78.21%; H 10.21%; O 11.58% | DFC |
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Melting Point | -8.1 oC | |
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Boiling Point | Bp10 89° | DFC |
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Experimental Water Solubility | 12 mg/mL at 25 oC | PARRISH,CF (1983) |
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Experimental logP | 1.70 | VEITH,GD ET AL. (1980) |
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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 | d2020 0.92 | DFC |
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Refractive Index | n20D 1.4759 | 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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GC-MS | 3,5,5-Trimethyl-2-cyclohexen-1-one, non-derivatized, GC-MS Spectrum | splash10-001i-9000000000-8ed7b012531653c3a41e | Spectrum | GC-MS | 3,5,5-Trimethyl-2-cyclohexen-1-one, non-derivatized, GC-MS Spectrum | splash10-001i-9200000000-e8bfe4751592e28e4c9e | Spectrum | GC-MS | 3,5,5-Trimethyl-2-cyclohexen-1-one, non-derivatized, GC-MS Spectrum | splash10-000i-2900000000-44ee32aafc71c88ceb86 | Spectrum | GC-MS | 3,5,5-Trimethyl-2-cyclohexen-1-one, non-derivatized, GC-MS Spectrum | splash10-001i-9000000000-35f5f51e1d1c8b9f41eb | Spectrum | GC-MS | 3,5,5-Trimethyl-2-cyclohexen-1-one, non-derivatized, GC-MS Spectrum | splash10-001i-9000000000-8ed7b012531653c3a41e | Spectrum | GC-MS | 3,5,5-Trimethyl-2-cyclohexen-1-one, non-derivatized, GC-MS Spectrum | splash10-001i-9200000000-e8bfe4751592e28e4c9e | Spectrum | GC-MS | 3,5,5-Trimethyl-2-cyclohexen-1-one, non-derivatized, GC-MS Spectrum | splash10-000i-2900000000-44ee32aafc71c88ceb86 | Spectrum | GC-MS | 3,5,5-Trimethyl-2-cyclohexen-1-one, non-derivatized, GC-MS Spectrum | splash10-001i-9000000000-35f5f51e1d1c8b9f41eb | Spectrum | Predicted GC-MS | 3,5,5-Trimethyl-2-cyclohexen-1-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-008i-9300000000-2b6a3c30cc2cb9b7c81d | Spectrum | Predicted GC-MS | 3,5,5-Trimethyl-2-cyclohexen-1-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 3,5,5-Trimethyl-2-cyclohexen-1-one, 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 - 10V, Positive | splash10-000i-0900000000-c0e6d09278faa8f9f642 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0900000000-dccd82444801bb71001a | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-4900000000-5268782d409da6b9a25a | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-053u-9100000000-6b6035d03526824e4f4a | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-10c654c5b0e1c7d81428 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0900000000-f5ce7cb3d1f20b415ad9 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-007c-9600000000-8b2034251abbccebb739 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-9700000000-eaf3d45b160fad967728 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0560-9100000000-d0446ecf5f19dbc3eeae | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a7i-9000000000-49bfbbf2837b17d78898 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-928b413704490084a303 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0900000000-928b413704490084a303 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00xr-4900000000-88d428c6a2e6fff994aa | 2021-09-23 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 6296 |
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ChEMBL ID | CHEMBL1882894 |
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KEGG Compound ID | C14743 |
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Pubchem Compound ID | 6544 |
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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 | HMDB31195 |
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CRC / DFC (Dictionary of Food Compounds) ID | CTL71-V:CTL71-V |
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EAFUS ID | 1901 |
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Dr. Duke ID | ISOPHORONE|3,5,5-TRIMETHYLCYCLOHEX-2-ENONE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00030540 |
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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 | rw1036811 |
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SuperScent ID | 6544 |
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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 | Not Available |
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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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camphoraceous |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| tobacco |
- 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.
| cooling |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| woody |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| sweet |
- 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.
| camphor |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| fruity |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| musty |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| cedarwood |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| leather |
- 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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