Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2006-08-13 19:43:36 UTC |
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Update Date | 2023-02-21 17:17:03 UTC |
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HMDB ID | HMDB0004487 |
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Secondary Accession Numbers | - HMDB0061788
- HMDB04487
- HMDB61788
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Metabolite Identification |
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Common Name | (S)-Carvone |
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Description | Carvone, with R and S isomers, also known as carvol or limonen-6-one, 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. Carvone is a neutral compound. Carvone is a naturally occurring organic compound found in many essential oils but is most abundant in the oils from caraway seeds (Carum carvi), spearmint (Mentha spicata), and dill (PMID:27427817 ). Carvone is occasionally found as a component of biological fluids in normal individuals. Both carvones (R, S) are used in the food and flavor industry (http//doi:10.1016/j.foodchem.2005.01.003). R-carvone is also used in air freshening products and in essential oils used in aromatherapy and alternative medicine. Caraway was used for medicinal purposes by the ancient Romans, but carvone was probably not isolated as a pure compound until Varrentrapp obtained it in 1841 (PMID:5556886 , 2477620 ). Carvone may help in the management of diseases (PMID:30374904 ) and had been considered as an adjuvant for treatment of cancer patients (PMID:30087792 ) and patients with epilepsy (PMID:31239862 ). It also has been successfully used as a biopesticide (PMID:30250476 ). |
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Structure | CC(=C)[C@H]1CC=C(C)C(=O)C1 InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m0/s1 |
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Synonyms | Value | Source |
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(+)-(4S)-Carvone | ChEBI | (+)-(S)-Carvone | ChEBI | (5S)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-one | ChEBI | (S)-(+)-Carvone | ChEBI | (S)-(+)-p-Mentha-6,8-dien-2-one | ChEBI | (S)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-one | ChEBI | (S)-2-Methyl-5-(1-methylvinyl)cyclohex-2-en-1-one | ChEBI | (S)-5-Isopropenyl-2-methylcyclohex-2-en-1-one | ChEBI | Carvol | ChEBI | Carvone | ChEBI | D-(+)-Carvone | ChEBI | D-Carvone | ChEBI | (+)-Carvone | Kegg | 2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-one | HMDB | D-p-Mentha-6,8(9)-dien-2-one | HMDB | (S)-Carvone | ChEBI |
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Chemical Formula | C10H14O |
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Average Molecular Weight | 150.2176 |
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Monoisotopic Molecular Weight | 150.10446507 |
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IUPAC Name | (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one |
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Traditional Name | carvone, (+)- |
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CAS Registry Number | 2244-16-8 |
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SMILES | CC(=C)[C@H]1CC=C(C)C(=O)C1 |
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InChI Identifier | InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m0/s1 |
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InChI Key | ULDHMXUKGWMISQ-VIFPVBQESA-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
- 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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Physiological effect | |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Liquid |
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Experimental Molecular Properties | |
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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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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(S)-Carvone,1TMS,isomer #1 | C=C(C)[C@@H]1C=C(O[Si](C)(C)C)C(C)=CC1 | 1385.2 | Semi standard non polar | 33892256 | (S)-Carvone,1TMS,isomer #1 | C=C(C)[C@@H]1C=C(O[Si](C)(C)C)C(C)=CC1 | 1361.3 | Standard non polar | 33892256 | (S)-Carvone,1TMS,isomer #1 | C=C(C)[C@@H]1C=C(O[Si](C)(C)C)C(C)=CC1 | 1648.9 | Standard polar | 33892256 | (S)-Carvone,1TBDMS,isomer #1 | C=C(C)[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)C(C)=CC1 | 1615.6 | Semi standard non polar | 33892256 | (S)-Carvone,1TBDMS,isomer #1 | C=C(C)[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)C(C)=CC1 | 1537.6 | Standard non polar | 33892256 | (S)-Carvone,1TBDMS,isomer #1 | C=C(C)[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)C(C)=CC1 | 1808.2 | Standard polar | 33892256 |
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Spectra |
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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 - (S)-Carvone EI-B (Non-derivatized) | splash10-0a59-9200000000-b8485ca29dc163ef7386 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - (S)-Carvone EI-B (Non-derivatized) | splash10-0a59-9200000000-b8485ca29dc163ef7386 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - (S)-Carvone EI-B (Non-derivatized) | splash10-0a59-9300000000-0663a3956cbefc28418a | 2018-05-25 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - (S)-Carvone EI-B (Non-derivatized) | splash10-0a59-9300000000-0663a3956cbefc28418a | 2018-05-25 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - (S)-Carvone EI-B (Non-derivatized) | splash10-0a59-9300000000-0663a3956cbefc28418a | 2018-05-25 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - (S)-Carvone EI-B (Non-derivatized) | splash10-0a59-9300000000-0663a3956cbefc28418a | 2018-05-25 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (S)-Carvone GC-MS (Non-derivatized) - 70eV, Positive | splash10-0f8l-9200000000-0d07518eb09c4d6d7512 | 2016-09-22 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (S)-Carvone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (S)-Carvone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0kai-9200000000-87c2472a96aad69404af | 2015-03-01 | Not Available | 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 - (S)-Carvone Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-0pb9-0900000000-cad4b73ca0349a0fca73 | 2012-07-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (S)-Carvone Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-0a4l-9700000000-4f8b99aefc0ccf7e31f4 | 2012-07-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (S)-Carvone Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-052f-9600000000-9902205f6d338c08818d | 2012-07-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (S)-Carvone EI-B (JEOL JMS-D-300) , Positive-QTOF | splash10-0a59-9200000000-b8485ca29dc163ef7386 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (S)-Carvone 20V, Negative-QTOF | splash10-0a59-9300000000-4251d272babda4de5c36 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (S)-Carvone 40V, Negative-QTOF | splash10-014i-5900000000-424a2cd188d1d2f5213d | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (S)-Carvone 10V, Negative-QTOF | splash10-0002-2900000000-8101d73f0cfb2435bca7 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (S)-Carvone 20V, Positive-QTOF | splash10-0aou-9200000000-f171ea0515bba0d8369d | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (S)-Carvone 10V, Positive-QTOF | splash10-0udj-9500000000-9859933bdc05bac9d663 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (S)-Carvone 40V, Positive-QTOF | splash10-00ou-9100000000-935629946779efc8b4ff | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-Carvone 10V, Positive-QTOF | splash10-0udi-0900000000-62861ac4cbf0b95e5069 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-Carvone 20V, Positive-QTOF | splash10-0udi-5900000000-b282dcb5d4a98c3f852f | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-Carvone 40V, Positive-QTOF | splash10-1000-9100000000-0fd631d26260645c64ae | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-Carvone 10V, Negative-QTOF | splash10-0002-0900000000-97d37f99bcaf0ed7d108 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-Carvone 20V, Negative-QTOF | splash10-0002-0900000000-1817a8dceee7a31df4e0 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-Carvone 40V, Negative-QTOF | splash10-001l-6900000000-581a45ee1ec95e201138 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-Carvone 10V, Positive-QTOF | splash10-0a4i-3900000000-f279f95a33eb225c1b14 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-Carvone 20V, Positive-QTOF | splash10-07eg-9400000000-34f0a30acb50659192b6 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-Carvone 40V, Positive-QTOF | splash10-00mo-9000000000-7b658cbdc17dd03f44ed | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-Carvone 10V, Negative-QTOF | splash10-0002-0900000000-22917433edc8ad9dbc2e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-Carvone 20V, Negative-QTOF | splash10-0002-0900000000-c0270d719fd67ba328d9 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-Carvone 40V, Negative-QTOF | splash10-001j-9700000000-dfa5cb40b47870793316 | 2021-09-24 | 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 | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, 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+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Not Specified | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Breast cancer | | details |
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Associated Disorders and Diseases |
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Disease References | Perillyl alcohol administration for cancer treatment |
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- Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB013718 |
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KNApSAcK ID | C00010891 |
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Chemspider ID | 15855 |
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KEGG Compound ID | C11383 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 16724 |
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PDB ID | Not Available |
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ChEBI ID | 15399 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1007121 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [PubMed:5556886 ]
- Hahn I, Scherer PW, Mozell MM: A mass transport model of olfaction. J Theor Biol. 1994 Mar 21;167(2):115-28. [PubMed:8207942 ]
- Jager W, Mayer M, Reznicek G, Buchbauer G: Percutaneous absorption of the montoterperne carvone: implication of stereoselective metabolism on blood levels. J Pharm Pharmacol. 2001 May;53(5):637-42. [PubMed:11370703 ]
- Inglik N, Rudenko BA, Kakhnovskii IM, Koroleva TV: [Gas chromatographic study of the composition of the volatile components of the urine in normal subjects and patients with diabetes mellitus]. Lab Delo. 1989;(8):24-7. [PubMed:2477620 ]
- McHugh D, Hu SS, Rimmerman N, Juknat A, Vogel Z, Walker JM, Bradshaw HB: N-arachidonoyl glycine, an abundant endogenous lipid, potently drives directed cellular migration through GPR18, the putative abnormal cannabidiol receptor. BMC Neurosci. 2010 Mar 26;11:44. doi: 10.1186/1471-2202-11-44. [PubMed:20346144 ]
- Tauber S, Paulsen K, Wolf S, Synwoldt P, Pahl A, Schneider-Stock R, Ullrich O: Regulation of MMP-9 by a WIN-binding site in the monocyte-macrophage system independent from cannabinoid receptors. PLoS One. 2012;7(11):e48272. doi: 10.1371/journal.pone.0048272. Epub 2012 Nov 6. [PubMed:23139770 ]
- Bondarenko AI, Drachuk K, Panasiuk O, Sagach V, Deak AT, Malli R, Graier WF: N-Arachidonoyl glycine suppresses Na(+)/Ca(2)(+) exchanger-mediated Ca(2)(+) entry into endothelial cells and activates BK(Ca) channels independently of GPCRs. Br J Pharmacol. 2013 Jun;169(4):933-48. doi: 10.1111/bph.12180. [PubMed:23517055 ]
- Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- de Groot AC, Schmidt E: Essential Oils, Part III: Chemical Composition. Dermatitis. 2016 Jul-Aug;27(4):161-9. doi: 10.1097/DER.0000000000000193. [PubMed:27427817 ]
- Mahboubi M: Caraway as Important Medicinal Plants in Management of Diseases. Nat Prod Bioprospect. 2019 Jan;9(1):1-11. doi: 10.1007/s13659-018-0190-x. Epub 2018 Oct 29. [PubMed:30374904 ]
- Mollazadeh H, Afshari AR, Hosseinzadeh H: Review on the Potential Therapeutic Roles of Nigella sativa in the Treatment of Patients with Cancer: Involvement of Apoptosis: - Black cumin and cancer. J Pharmacopuncture. 2017 Sep;20(3):158-172. doi: 10.3831/KPI.2017.20.019. Epub 2017 Sep 30. [PubMed:30087792 ]
- Bahr TA, Rodriguez D, Beaumont C, Allred K: The Effects of Various Essential Oils on Epilepsy and Acute Seizure: A Systematic Review. Evid Based Complement Alternat Med. 2019 May 22;2019:6216745. doi: 10.1155/2019/6216745. eCollection 2019. [PubMed:31239862 ]
- Singh P, Pandey AK: Prospective of Essential Oils of the Genus Mentha as Biopesticides: A Review. Front Plant Sci. 2018 Sep 10;9:1295. doi: 10.3389/fpls.2018.01295. eCollection 2018. [PubMed:30250476 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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