Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:55 UTC |
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Update date | 2019-11-26 03:09:05 UTC |
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Primary ID | FDB013800 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | (-)-Menthone |
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Description | Occurs with menthol in many essential oils including peppermint and geranium oils. It is used in flavour compositions
L-Menthone is the most abundant in nature of the four possible stereoisomers. Menthone is used in perfumery and cosmetics for its characteristic aromatic and minty odor. (-)-Menthone is found in many foods, some of which are ohelo berry, rocket salad, cauliflower, and common hazelnut. |
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CAS Number | 14073-97-3 |
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Structure | |
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Synonyms | Synonym | Source |
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(1S,4R)-Menthone | ChEBI | (1S,4R)-p-Menthan-3-one | ChEBI | (2R,5S)-2-Isopropyl-5-methylcyclohexanone | ChEBI | (+)-(1S,4R)-Menthone | HMDB | (2R,5S)-5-Methyl-2-(propan-2-yl)cyclohexanone | HMDB | Menthone | MeSH, HMDB | (+)-Menthone | HMDB | (2R,5S)-5-Methyl-2-(1-methylethyl)cyclohexanone | HMDB | D-Menthone | HMDB | (-)-(1R,4S)-Menthone | biospider | (-)-(2S,5R)-Menthone | biospider | (-)-5-Methyl-2-(1-methylethyl)cyclohexanone | biospider | (-)-Menthone | db_source | (1R,4S)-(-)-p-Menthan-3-one | manual | (1R,4S)-p-Menthan-3-one | biospider | (2S-trans)-5-Methyl-2-(1-methylethyl)cyclohexanone | biospider | (2S, 5R)-trans-2-Isopropyl-5-methylcyclohexanone | HMDB | (2S,5R)-2-Isopropyl-5-methylcyclohexanone | biospider | (2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexanone | biospider | (2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexanone | biospider | (2S,5R)-Menthone | ChEBI | (2S,5R)-trans-2-Isopropyl-5-methylcyclohexanone | manual | 5-Methyl-2-(1-methylethyl)-(2S-trans)-cyclohexanone | HMDB | 5-Methyl-2-(1-methylethyl)-(2S,5R)-cyclohexanone | HMDB | Cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2S-trans)- | biospider | Cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2S,5R)- | biospider | L-Menthone | manual |
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Predicted Properties | |
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Chemical Formula | C10H18O |
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IUPAC name | (2R,5S)-5-methyl-2-(propan-2-yl)cyclohexan-1-one |
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InChI Identifier | InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3 |
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InChI Key | NFLGAXVYCFJBMK-UHFFFAOYSA-N |
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Isomeric SMILES | CC(C)C1CCC(C)CC1=O |
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Average Molecular Weight | 154.2493 |
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Monoisotopic Molecular Weight | 154.135765198 |
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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
- Cyclic ketone
- Ketone
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- 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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Process | Naturally occurring process: |
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Role | Biological role: |
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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 | Liquid | |
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Physical Description | Not Available | |
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Mass Composition | C 77.87%; H 11.76%; O 10.37% | DFC |
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Melting Point | Mp -6° | DFC |
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Boiling Point | Bp 207° | DFC |
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Experimental Water Solubility | 0.497 mg/mL at 25 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Experimental logP | 3.05 | 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 | [a]20D -24.8 | DFC |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | n23D 1.4490 | 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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Predicted GC-MS | (+)-Menthone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-06r7-9300000000-1d150f2cf0a23dbfef0b | Spectrum | Predicted GC-MS | (+)-Menthone, 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 | splash10-0a4i-0900000000-fa99f8c083212e4f2fc3 | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0bt9-9800000000-7bf975ea31bcef83aa61 | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0aor-9000000000-3f8923896797c4486693 | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0900000000-d55afdef2faae68197a6 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0900000000-91ec697d11dad181a342 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-01oy-9600000000-7933610ac6051fc8ef81 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0900000000-d2363ae8d4dbdcccda80 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0900000000-084e13e285859f435a61 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0gbc-9700000000-57929498deae48afce7a | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0bti-3900000000-5b9ac9ca9aaff729e2d1 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0532-9200000000-ac0243da1ad4aa3d859e | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-d3a7bbb5abb9a0381a39 | 2021-09-22 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 24636 |
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ChEMBL ID | CHEMBL276311 |
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KEGG Compound ID | C00843 |
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Pubchem Compound ID | 26447 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 15410 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB35162 |
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CRC / DFC (Dictionary of Food Compounds) ID | JHQ37-H:JHL57-O |
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EAFUS ID | Not Available |
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Dr. Duke ID | (-)-MENTHONE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00000811 |
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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 | rw1008131 |
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SuperScent ID | 26447 |
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Wikipedia ID | Menthone |
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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 EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid. | 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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raspberry |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| camphoraceous |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| deep |
- 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.
| peppermint |
- 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.
| camphor |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| bitter |
- Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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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 | — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181. — 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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