Record Information |
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Version | 1.0 |
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Created at | 2020-03-19 00:32:15 UTC |
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Updated at | 2020-12-07 19:07:22 UTC |
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CannabisDB ID | CDB000348 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | Pulegone |
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Description | Pulegone 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. It is formally classified as a cyclic ketone although it is biochemically a monoterpenoid as it is synthesized via isoprene units. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plant cell plastids (PMID: 7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Pulegone is a hydrophobic, neutral compound that is insoluble in water. It exists as a clear, colorless oil. There are two isomers of Pulegone (the R and the S isomer), with the R isomer being more common. It is used industrially as a food additive and a perfuming agent. Pulegone has a fresh, minty or peppermint odor and a minty, fruity or green taste. It is found naturally in the essential oils of a variety of plants such as Nepeta cataria (catnip), Hedeoma pulegioides (pennyroyal), and Mentha species. It is also found in a number of plant foods and spices such as blackberryies, black currants, bell peppers, cornmint, rosemary, black tea, thyme, orange mint, peppermint, and spearmint, which makes it a potential biomarker for the consumption of these food products. Pulegone is also one of more than 140 terpenes that are found in cannabis plants (PMID: 6991645 ). |
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Structure | |
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Synonyms | Value | Source |
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(+)-(R)-Pulegone | ChEBI | (1R)-(+)-p-Menth-4(8)-en-3-one | ChEBI | (5R)-2-Isopropylidene-5-methylcyclohexanone | ChEBI | (R)-Pulegone | ChEBI | D-Pulegone | ChEBI | (+)-Pulegone | Kegg | Pulegone, (R)-isomer | HMDB | (R)-(+)-p-Menth-4(8)-en-3-one | HMDB | (R)-p-Menth-4(8)-en-3-one | HMDB | p-Menth-4(8)-en-3-one | HMDB | (R)-5-Methyl-2-(1-methylethylidene)cyclohexanone | HMDB | (R)-(+)-Pulegone | HMDB | (1R)-Pulegone | HMDB | L-Pulegone | HMDB | NSC 15334 | HMDB | Pulegon | HMDB | FEMA 2963 | HMDB | (+)-4(8)-Para-menthen-3-one | HMDB | 5-Methyl-2-(1-methylethylidene)cyclohexanone | HMDB | Pulegone | ChEBI | (5R)-5-Methyl-2-(1-methylethylidene)cyclohexanone | PhytoBank |
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Chemical Formula | C10H16O |
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Average Molecular Weight | 152.23 |
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Monoisotopic Molecular Weight | 152.1201 |
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IUPAC Name | (5R)-5-methyl-2-(propan-2-ylidene)cyclohexan-1-one |
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Traditional Name | (+)-pulegone |
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CAS Registry Number | 89-82-7 |
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SMILES | C[C@@H]1CCC(=C(C)C)C(=O)C1 |
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InChI Identifier | InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1 |
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InChI Key | NZGWDASTMWDZIW-MRVPVSSYSA-N |
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Chemical Taxonomy |
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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: Biological location: Source: |
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Role | Industrial application: Biological role: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | < 25 °C | Not Available | Boiling Point | 224 °C | Wikipedia | Water Solubility | Not Available | Not Available | logP | 3.08 | Not Available |
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Predicted Properties | [] |
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Spectra |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0kur-9400000000-182826a9f81c661c7496 | 2015-03-01 | View Spectrum | GC-MS | Pulegone , non-derivatized, GC-MS Spectrum | splash10-0f89-9200000000-103da19d7e73140f53a7 | Spectrum | GC-MS | Pulegone , non-derivatized, GC-MS Spectrum | splash10-0fsi-9300000000-5c40f6bc1c5dd5e64dc8 | Spectrum | Predicted GC-MS | Pulegone , non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0btm-9600000000-72752a4904dbe00f2b4a | Spectrum | Predicted GC-MS | Pulegone , non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Pulegone , 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-0900000000-50f4b6a38ec680e83d0c | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-114i-6900000000-04a7ff4ee15b9b1c8161 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ldi-9100000000-2aee3b73ef815011023f | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0900000000-cd90c558f842f253efd3 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0900000000-011197e33d9b4420c257 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4u-6900000000-723bf6d0a35d2e10aafd | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0ik9-2900000000-7f3925a428ada570a2f6 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00l6-9300000000-2fd8486379bd720b7b38 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-441dfa2e182dd78429bc | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0900000000-c373c9eea3cebf186f53 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0900000000-9fc5f57a10d95a4f369b | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-5900000000-7ce0df14de5e9c637a48 | 2021-09-24 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50.18 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum |
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Pathways |
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Pathways | Not Available |
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Protein Targets |
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Enzymes | Not Available |
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Transporters | Not Available |
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Metal Bindings | Not Available |
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Receptors | Not Available |
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Transcriptional Factors | Not Available |
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Concentrations Data |
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External Links |
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HMDB ID | HMDB0035604 |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB030074 |
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KNApSAcK ID | C00000827 |
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Chemspider ID | 390923 |
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KEGG Compound ID | C09893 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Pulegone |
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METLIN ID | Not Available |
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PubChem Compound | 442495 |
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PDB ID | Not Available |
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ChEBI ID | 35596 |
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References |
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General References | - McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
- Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
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