Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:11:17 UTC |
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Update date | 2019-11-26 03:10:07 UTC |
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Primary ID | FDB014467 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | (S)-Piperitone |
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Description | Common constituent of Mentha subspecies oils
Piperitone is a natural monoterpene ketone which is a component of some essential oils. Both stereoisomers, the D-form and the L-form, are known. The D-form has a peppermint-like aroma and has been isolated from the oils of plants from the genera Cymbopogon, Andropogon, and Mentha. The L-form has been isolated from Sitka spruce. (S)-Piperitone is found in mentha (mint), cornmint, and herbs and spices. |
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CAS Number | 6091-50-5 |
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Structure | |
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Synonyms | Synonym | Source |
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(S)-3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-one | ChEBI | (S)-Piperitone | ChEBI | alpha-Piperitone | ChEBI | D-Piperitone | ChEBI | a-Piperitone | Generator | Α-piperitone | Generator | (-)-Piperitone | HMDB | (6R)-3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-one | HMDB | (6R)-3-Methyl-6-(propan-2-yl)cyclohex-2-en-1-one | HMDB | (6R)-6-Isopropyl-3-methylcyclohex-2-en-1-one | HMDB | L-Piperitone | HMDB | (+)-Piperitone | biospider | (6S)-3-Methyl-6-(propan-2-yl)cyclohex-2-en-1-one | biospider | 2-Cyclohexen-1-one, 3-methyl-6-(1-methylethyl)-, (S)- | biospider | 3-Methyl-6-(1-methylethyl)-(S)-2-cyclohexen-1-one | HMDB | 3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-one, (S)- | biospider | α-piperitone | Generator |
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Predicted Properties | |
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Chemical Formula | C10H16O |
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IUPAC name | (6S)-3-methyl-6-(propan-2-yl)cyclohex-2-en-1-one |
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InChI Identifier | InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3/t9-/m0/s1 |
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InChI Key | YSTPAHQEHQSRJD-VIFPVBQESA-N |
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Isomeric SMILES | CC(C)[C@@H]1CCC(C)=CC1=O |
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Average Molecular Weight | 152.2334 |
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Monoisotopic Molecular Weight | 152.120115134 |
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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
- 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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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 | C 78.90%; H 10.59%; O 10.51% | DFC |
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Melting Point | Not Available | |
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Boiling Point | Bp20 116-118.5° | 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]20D +49.13 | 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 | (R)-Piperitone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00kf-9300000000-e3bec6231e4993e3d578 | Spectrum | Predicted GC-MS | (R)-Piperitone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (R)-Piperitone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (R)-Piperitone, 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-0900000000-0f2176d975b2f9bfe7fd | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0w29-7900000000-bc07a247759df113c943 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4l-9000000000-6e8d2587c3fab7a87b03 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0900000000-83fb585962f6ed48b378 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0900000000-a2b215f78ea2edceb56c | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4u-8900000000-058070ac2054c97f9a30 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0w29-1900000000-cf5ff8ec6a34a5b6435b | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0gb9-9200000000-ddaec970d54edc7cbf79 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00kf-9000000000-4c75828fad35f0eec374 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0900000000-c373c9eea3cebf186f53 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0900000000-3f9a24ef7ca3da32a522 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-9400000000-172af5b361384699caf7 | 2021-09-22 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 55294 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C09885 |
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Pubchem Compound ID | 61362 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 41 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB35738 |
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CRC / DFC (Dictionary of Food Compounds) ID | JFJ29-J:JQZ91-X |
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EAFUS ID | 3057 |
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Dr. Duke ID | (+)-PIPERITONE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00003054 |
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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 | rw1002881 |
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SuperScent ID | Not Available |
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Wikipedia ID | Piperitone |
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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 | Not Available |
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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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peppermint |
- 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.
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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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