| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:12:10 UTC |
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| Update date | 2020-09-17 15:30:28 UTC |
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| Primary ID | FDB015974 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Piperitenone |
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| Description | Piperitenone belongs to the class of organic compounds known as menthane 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, piperitenone is an isoprenoid lipid molecule. It is very hydrophobic, almost insoluble in water, and relatively neutral. Piperitenone is a minty, phenolic, and sharp-taste ( http://www.thegoodscentscompany.com/data/rw1031141.html). Piperitenone is found in highest concentrations in spearmints and rosemaries. It was detected in peppermints, herbs and spices, orange mints, citrus, and mentha (mint). This could make piperitenone a potential biomarker for the consumption of these foods. |
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| CAS Number | 491-09-8 |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C10H14O |
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| IUPAC name | 3-methyl-6-(propan-2-ylidene)cyclohex-2-en-1-one |
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| InChI Identifier | InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h6H,4-5H2,1-3H3 |
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| InChI Key | HKZQJZIFODOLFR-UHFFFAOYSA-N |
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| Isomeric SMILES | CC(C)=C1CCC(C)=CC1=O |
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| Average Molecular Weight | 150.2176 |
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| Monoisotopic Molecular Weight | 150.10446507 |
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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
- Quinomethane
- O-quinomethane
- Cyclohexenone
- 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: 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 | |
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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 | Piperitenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0f7c-8900000000-f5b1034f0ad5612f0f1e | Spectrum | | Predicted GC-MS | Piperitenone, 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 | splash10-0udi-0900000000-c4031753132982c55fab | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0pb9-7900000000-9a0d9372d2684846d39b | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0gb9-9100000000-82fba962be7e9686c517 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-b7c0004066c195aa4089 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0900000000-49abeb92134d82dda90e | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-053s-2900000000-fba0f16e8603dd89ee04 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-1900000000-7be39bdd81d4a83f56ee | 2021-09-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00kf-9300000000-b6529814b27363caeb9a | 2021-09-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-51ccd861c84166dd6b2c | 2021-09-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-22917433edc8ad9dbc2e | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0900000000-cfb5c45cee930f53ee1b | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0159-9100000000-afc2d70a9cbeb08c1230 | 2021-09-25 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 337757 |
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| ChEMBL ID | CHEMBL54161 |
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| KEGG Compound ID | C01951 |
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| Pubchem Compound ID | 381152 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | 17304 |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB36999 |
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| CRC / DFC (Dictionary of Food Compounds) ID | KLQ60-W:KLQ60-W |
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| EAFUS ID | 3055 |
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| Dr. Duke ID | (+)-PIPERITENONE|PIPERITENONE |
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| BIGG ID | Not Available |
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| KNApSAcK ID | C00010889 |
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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 | rw1031141 |
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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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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | |
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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 | |
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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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