Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-08-13 02:18:06 UTC |
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Update Date | 2023-02-21 17:16:45 UTC |
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HMDB ID | HMDB0003634 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Perillyl alcohol |
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Description | Perillyl alcohol is a monoterpene isolated from the essential oils of lavendin, peppermint, spearmint, cherries, celery seeds, and several other plants. In animal studies it has been shown to regress pancreatic, mammary, and liver tumors, to exhibit possible application as a chemopreventative agent for colon, skin, and lung cancer, and as a chemotherapeutic agent for neuroblastoma, and prostate and colon cancer.(PMID:9855569 ). |
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Structure | InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3 |
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Synonyms | Value | Source |
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1-Hydroxymethyl-4-isopropenyl-1-cyclohexene | ChEBI | 1-Perillalcohol | ChEBI | 4-(1-Methylethenyl)-1-cyclohexene-1-methanol | ChEBI | 4-Isopropenyl-1-cyclohexene carbinol | ChEBI | 4-Isopropenylcyclohex-1-en-1-ylmethanol | ChEBI | Dihydrocuminyl alcoholn | ChEBI | Isocarveol | ChEBI | p-Mentha-1,8-dien-7-ol | ChEBI | Perilla alcohol | ChEBI | Perillol | ChEBI | (-)-Perillyl alcohol | HMDB | (S)-(-)-Perillyl alcohol | HMDB | 1,8-p-Menthadien-7-ol | HMDB | 4-Isopropenyl-cyclohex-1-ene-1-methanol | HMDB | Dihydrocuminic alcohol | HMDB | Dihydrocuminyl alcohol | HMDB | Hydrocumin alcohol | HMDB | Iso-carveol | HMDB | Para-mentha-1,8-dien-7-ol | HMDB | Perill alcohol | HMDB | Perillic alcohol | HMDB | Cyclohex-1-ene-1-methanol, 4(1-methylethenyl) | HMDB | Perilla alcohol, (S)-isomer | HMDB | Perilla alcohol, (R)-isomer | HMDB | (-)-p-Mentha-1,8-dien-7-ol | HMDB | (S)-Perillyl alcohol | HMDB |
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Chemical Formula | C10H16O |
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Average Molecular Weight | 152.237 |
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Monoisotopic Molecular Weight | 152.120115135 |
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IUPAC Name | [4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol |
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Traditional Name | (-)-perillylalcohol |
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CAS Registry Number | 536-59-4 |
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SMILES | CC(=C)C1CCC(CO)=CC1 |
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InChI Identifier | InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3 |
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InChI Key | NDTYTMIUWGWIMO-UHFFFAOYSA-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
- Organic oxygen compound
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Alcohol
- 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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Physiological effect | |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 244 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | 3.17 | GRIFFIN,S ET AL. (1999) |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Perillyl alcohol GC-MS (1 TMS) | splash10-0006-9600000000-852faf99c20eb91e9836 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Perillyl alcohol EI-B (Non-derivatized) | splash10-00mo-9200000000-6d3cda5b991dc6f0a098 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Perillyl alcohol EI-B (Non-derivatized) | splash10-014l-9300000000-f32f7e87d33288c8045d | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Perillyl alcohol GC-MS (Non-derivatized) | splash10-0006-9600000000-852faf99c20eb91e9836 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Perillyl alcohol GC-MS (Non-derivatized) - 70eV, Positive | splash10-007x-9400000000-0642824f11b9c7fd315d | 2016-09-22 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Perillyl alcohol GC-MS (1 TMS) - 70eV, Positive | splash10-05gu-9510000000-9f19c403be332e74c8ad | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Perillyl alcohol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Perillyl alcohol Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-00du-3900000000-a6c07543feea874fe65d | 2012-07-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Perillyl alcohol Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-004u-9000000000-352e042e70150a70fc17 | 2012-07-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Perillyl alcohol Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-0bvj-9000000000-9a2da0a6d60335f43f46 | 2012-07-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Perillyl alcohol EI-B (HITACHI M-80B) , Positive-QTOF | splash10-00mo-9200000000-81544f3016fa24bad81f | 2012-08-31 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Perillyl alcohol 10V, Positive-QTOF | splash10-0udr-1900000000-2f012741782fc72aa3df | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Perillyl alcohol 20V, Positive-QTOF | splash10-000i-5900000000-849092ef4eeddd440687 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Perillyl alcohol 40V, Positive-QTOF | splash10-0gc0-9200000000-fd4b15fd9437d4b70409 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Perillyl alcohol 10V, Negative-QTOF | splash10-0udi-0900000000-20d0d9f448f90e31136f | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Perillyl alcohol 20V, Negative-QTOF | splash10-0uk9-0900000000-a390120b9758e2ca2f5d | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Perillyl alcohol 40V, Negative-QTOF | splash10-00di-4900000000-39d18f7a3231672157f5 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Perillyl alcohol 10V, Negative-QTOF | splash10-0udi-0900000000-c373c9eea3cebf186f53 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Perillyl alcohol 20V, Negative-QTOF | splash10-001i-0900000000-8fa95dbd5fa627e933fa | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Perillyl alcohol 40V, Negative-QTOF | splash10-014i-9200000000-7da801ed46abad2dd628 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Perillyl alcohol 10V, Positive-QTOF | splash10-0f84-9800000000-bd8e7097a31172f8ad0e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Perillyl alcohol 20V, Positive-QTOF | splash10-0006-9200000000-373d4892dedc5ff6266f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Perillyl alcohol 40V, Positive-QTOF | splash10-00mo-9000000000-a6d86d2ceee0f1021fd3 | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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