| Record Information |
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| Version | 1.0 |
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| Creation date | 2011-05-05 19:53:33 UTC |
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| Update date | 2019-11-26 03:20:56 UTC |
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| Primary ID | FDB021835 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | (±)-Isomenthol |
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| Description | (±)-isomenthol 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 (±)-isomenthol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (±)-isomenthol can be found in a number of food items such as cabbage, peppermint, sunflower, and white cabbage, which makes (±)-isomenthol a potential biomarker for the consumption of these food products. |
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| CAS Number | 3623-52-7 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| (±)-Isomenthol | db_source | | Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2S,5S)-rel- | manual | | DL-Isomenthol | manual | | Isomenthol | manual | | trans-1,3,cis-1,4-(±)-Menthol | manual |
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| Predicted Properties | |
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| Chemical Formula | C10H20O |
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| IUPAC name | (1R,2S,5S)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol |
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| InChI Identifier | InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9-,10+/m0/s1 |
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| InChI Key | NOOLISFMXDJSKH-LPEHRKFASA-N |
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| Isomeric SMILES | CC(C)[C@@H]1CC[C@H](C)C[C@H]1O |
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| Average Molecular Weight | 156.2652 |
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| Monoisotopic Molecular Weight | 156.151415262 |
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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 | Not Available |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | solid | |
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| Physical Description | Needles | DFC |
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| Mass Composition | C 76.86%; H 12.90%; O 10.24% | DFC |
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| Melting Point | Mp 53-54° | DFC |
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| Boiling Point | Bp 218.5-218.6° | 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 | 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 | Not Available |
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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-0900000000-0c54797416987a09fdc7 | 2019-02-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4r-6900000000-bd03de53003ab3ad94c3 | 2019-02-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9100000000-cdad8953e5a863785f4c | 2019-02-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0900000000-35bb57f3b1e1db7e0531 | 2019-02-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0900000000-6f5b57bb56920ed10bd2 | 2019-02-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0bvr-5900000000-291ecb7fa19007ee756b | 2019-02-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-05mk-9800000000-bb8a9e58bdc61e2654e6 | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-053e-9100000000-6405f7fe35f6f6bdc8c5 | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-fee5c7d55bf523973cbf | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0900000000-f6034c6a8245c68a37ac | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0900000000-7efa42d43b7858e2c2ce | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0zfr-0900000000-b6eef0a7f66ac7e97e78 | 2021-10-21 | 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 | Not Available |
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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 | JRL74-J:JFH81-J |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | ISOMENTHOL |
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| BIGG ID | Not Available |
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| KNApSAcK ID | C00035118 |
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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 | Not Available |
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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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| Anti acetylcholinesterase | 38462 | An agent that inhibits acetylcholinesterase, increasing acetylcholine levels. It enhances cholinergic transmission, used therapeutically to treat Alzheimer's disease, myasthenia gravis, and glaucoma, improving cognitive function, muscle strength, and reducing intraocular pressure. | 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 | Not Available |
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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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