Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:12:11 UTC |
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Update date | 2019-11-26 03:12:38 UTC |
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Primary ID | FDB016026 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Rotundifolone |
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Description | Rotundifolone belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. Rotundifolone is a herbal and minty tasting compound. Rotundifolone is found, on average, in the highest concentration within spearmints (Mentha spicata) and cornmints (Mentha arvensis). Rotundifolone has also been detected, but not quantified in, herbs and spices. This could make rotundifolone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Rotundifolone. |
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CAS Number | 5945-46-0 |
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Structure | |
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Synonyms | Synonym | Source |
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1,2-Epoxy-P-menth-4(8)-en-3-one | HMDB | 2,3-Epoxy-6-isopropylidene-3-methylcyclohexanone | HMDB | 6-Methyl-3-(1-methylethylidene)-7-oxabicyclo[4.1.0]heptan-2-one, 9ci | HMDB | Piperitenone oxide | HMDB | 6-Methyl-3-(1-methylethylidene)-7-oxabicyclo[4.1.0]heptan-2-one, 9CI | db_source | P-Menth-4(8)-en-3-one, 1,2-epoxy- | biospider | Rotundifolone | db_source |
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Predicted Properties | |
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Chemical Formula | C10H14O2 |
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IUPAC name | 6-methyl-3-(propan-2-ylidene)-7-oxabicyclo[4.1.0]heptan-2-one |
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InChI Identifier | InChI=1S/C10H14O2/c1-6(2)7-4-5-10(3)9(12-10)8(7)11/h9H,4-5H2,1-3H3 |
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InChI Key | AKASWINDKIEEBO-UHFFFAOYSA-N |
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Isomeric SMILES | CC(C)=C1CCC2(C)OC2C1=O |
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Average Molecular Weight | 166.217 |
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Monoisotopic Molecular Weight | 166.099379692 |
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Classification |
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Description | Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Oxepanes |
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Sub Class | Not Available |
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Direct Parent | Oxepanes |
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Alternative Parents | |
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Substituents | - Oxepane
- Ketone
- Oxacycle
- Ether
- Oxirane
- Dialkyl ether
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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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 | 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 | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 72.26%; H 8.49%; O 19.25% | DFC |
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Melting Point | Mp 27.5° | DFC |
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Boiling Point | Bp1 86° | 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 +166.5 (MeOH) | 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 | Rotundifolone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00o4-9300000000-28ac35eefccb97ecf8f7 | Spectrum | Predicted GC-MS | Rotundifolone, 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 | splash10-014i-0900000000-0d2244bb050ca70a3c49 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014i-4900000000-a49b13c97830692f36f0 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-067i-9100000000-5d3ca3ad1a2c8d254117 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0900000000-ab194c3e028cf03581b8 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-1900000000-a1934865dd6aa8ca0d4a | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a59-9600000000-37561a809cd7b097631e | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0900000000-349584a3f625d5b5807f | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0900000000-d1252c53df5aa0366a66 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-9300000000-442ba93afe2056decf39 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-1900000000-d8e5853d91f1eb90687c | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00kf-9300000000-0dfe3b6fd9baf52e4fd7 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-014l-9100000000-6c52be035dfdc4e36ed2 | 2021-09-24 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 55800 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 61942 |
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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 | HMDB37044 |
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CRC / DFC (Dictionary of Food Compounds) ID | KMC41-G:KMC41-G |
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EAFUS ID | 3056 |
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Dr. Duke ID | PIPERITENONE-OXIDE|(+)-PIPERITENONE-OXIDE |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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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 | rw1049431 |
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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 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 | insecticide | 24852 | Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects. | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | 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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herbal |
- 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 | — 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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