Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:08:30 UTC |
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Update date | 2019-11-26 03:03:26 UTC |
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Primary ID | FDB009285 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Dihydrocarveol |
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Description | Dihydrocarveol, also known as 2-methyl-5-(1-methylethenyl)cyclohexanol or 6-methyl-3-isopropenylcyclohexanol, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Dihydrocarveol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Dihydrocarveol is a herbal, menthol, and minty tasting compound and can be found in a number of food items such as dill, pepper (spice), pot marjoram, and wild celery, which makes dihydrocarveol a potential biomarker for the consumption of these food products. |
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CAS Number | 619-01-2 |
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Structure | |
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Synonyms | Synonym | Source |
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1,6-Dihydrocarveol | ChEBI | 2-Methyl-5-(1-methylethenyl)cyclohexanol | ChEBI | 2-Methyl-5-isopropenylcyclohexanol | ChEBI | 5-Isopropenyl-2-methylcyclohexanol | ChEBI | 6-Methyl-3-isopropenylcyclohexanol | ChEBI | 8-p-Menthen-2-ol | ChEBI | Menth-8-en-2-ol | ChEBI | 2-Methyl-5-(1-methylvinyl)cyclohexan-1-ol | MeSH | a Dihydrocarveol | ChEBI | 2-methyl-5-(1-methylvinyl)cyclohexan-1-ol | biospider | 2-methyl-5-(prop-1-en-2-yl)cyclohexanol | biospider | 2-methyl-5-isopropenylcyclohexanol | biospider | 6-Methyl-3-isopropylcyclohexanol | biospider | Carveol, dihydro- | biospider | p-Menth-8-en-2-ol | biospider |
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Predicted Properties | |
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Chemical Formula | C10H18O |
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IUPAC name | 2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-ol |
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InChI Identifier | InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-11H,1,4-6H2,2-3H3 |
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InChI Key | KRCZYMFUWVJCLI-UHFFFAOYSA-N |
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Isomeric SMILES | CC1CCC(CC1O)C(C)=C |
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Average Molecular Weight | 154.253 |
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Monoisotopic Molecular Weight | 154.1357652 |
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Classification |
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Description | Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. |
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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 | Menthane monoterpenoids |
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Alternative Parents | |
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Substituents | - P-menthane monoterpenoid
- Monocyclic monoterpenoid
- Cyclohexanol
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- 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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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 | Boiling Pt : 224.5 oC | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | 3.21 | GRIFFIN,S ET AL. (1999) |
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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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EI-MS | Mass Spectrum (Electron Ionization) | splash10-05mo-9200000000-da0a49ae0820607efcab | 2015-03-01 | View Spectrum | Predicted GC-MS | 1-Dihydrocarveol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-001i-9300000000-c4d08d4f42ce5380cea3 | 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 | splash10-052r-1900000000-426222b005de9ed263f7 | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-052r-7900000000-92669f5cd45165c58a8a | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0api-9100000000-a02a955b5b196ac361c3 | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0900000000-a7c7b44c65ac0d9983a9 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0900000000-08b2ced2412775e44ff3 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0f79-8900000000-ef61141645310f0e0a80 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0532-9400000000-959ea8fcd37ca9a711e5 | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00l5-9100000000-66dc6c3c3f3184c185af | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00kf-9000000000-09a8ec5e3424e50d627f | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udr-0900000000-6cb010728dc534ba406c | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0900000000-318736dc4101f232fc4c | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0udi-2900000000-9492df1cf75725527190 | 2021-10-21 | View Spectrum |
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NMR | |
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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 | C18017 |
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Pubchem Compound ID | 12072 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 50215 |
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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 | 910 |
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Dr. Duke ID | DIHYDROCARVEOL|P-MENTH-8-EN-2-OL |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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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 | 619-01-2 |
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GoodScent ID | rw1013231 |
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SuperScent ID | 12072 |
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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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flavor | 48318 | A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. | DUKE | irritant | | | 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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mint |
- 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
| spice |
- 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
| minty |
- 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.
| menthol |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| spearmint |
- 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.
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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).
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