Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:11:18 UTC |
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Update date | 2020-09-17 15:41:35 UTC |
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Primary ID | FDB014500 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | (+)-Neomenthol |
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Description | (+)-Neomenthol, also known as fema 2666, 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. Thus, (+)-neomenthol is considered to be an isoprenoid lipid molecule (+)-Neomenthol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. |
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CAS Number | 2216-52-6 |
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Structure | |
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Synonyms | Synonym | Source |
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(1S,2S,5R)-(+)-Neomenthol | HMDB | (1S,2S,5R)-2-Isopropyl-5-methylcyclohexanol | HMDB | (1S,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexan-1-ol | HMDB | (1S,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexanol | HMDB | D-Neomenthol | HMDB | FEMA 2666 | HMDB | (+)-Neomenthol | db_source | (1S,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol | biospider | (1S,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexanol | biospider | D-neomenthol | biospider |
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Predicted Properties | |
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Chemical Formula | C10H20O |
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IUPAC name | (1S,2S,5R)-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+/m1/s1 |
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InChI Key | NOOLISFMXDJSKH-UTLUCORTSA-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 | |
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Ontology |
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Disposition | Route of exposure: Biological location: Source: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological 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 76.86%; H 12.90%; O 10.24% | DFC |
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Melting Point | Mp -22° | DFC |
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Boiling Point | Bp14 83-84° | 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 | [a]10D +18.02 (neat) | DFC |
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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 | (+)-Neomenthol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-052f-9500000000-a610fe2868ba87b759ee | Spectrum | Predicted GC-MS | (+)-Neomenthol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-01w0-9520000000-26cc8cab97979ec9fb4d | Spectrum | Predicted GC-MS | (+)-Neomenthol, 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 | splash10-052r-0900000000-fc39fb91c62eb627e3af | 2015-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-052r-5900000000-839aa9da0c06f6d09968 | 2015-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0avi-9200000000-e9b33e704445c7e908ec | 2015-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0900000000-3a700dc611fb070e6b45 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0900000000-5a80eb79e919e06fa63a | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0bti-7900000000-67a39bf95581e52cb931 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-05mk-9800000000-bb8a9e58bdc61e2654e6 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-053e-9100000000-6405f7fe35f6f6bdc8c5 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-fee5c7d55bf523973cbf | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0900000000-f6034c6a8245c68a37ac | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0900000000-7efa42d43b7858e2c2ce | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0zfr-0900000000-b6eef0a7f66ac7e97e78 | 2021-09-24 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 388397 |
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ChEMBL ID | CHEMBL1907991 |
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KEGG Compound ID | C00553 |
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Pubchem Compound ID | 439263 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 15402 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB35763 |
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CRC / DFC (Dictionary of Food Compounds) ID | JRL74-J:JRL68-K |
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EAFUS ID | 2647 |
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Dr. Duke ID | (+)-NEOMENTHOL|NEOMENTHOL |
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BIGG ID | Not Available |
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KNApSAcK ID | C00000825 |
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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 | rw1060561 |
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SuperScent ID | 439263 |
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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-spasmodic | 52217 | An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort. | DUKE | Perfumery | 48318 | The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties. | 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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camphoraceous |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| mentholic |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| minty |
- 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.
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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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