Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:11:14 UTC |
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Update date | 2020-09-17 15:36:09 UTC |
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Primary ID | FDB014367 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | (+)-trans-Pinocarveol |
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Description | Trans-Pinocarveol or simply pinocarveol belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. 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-eritritol-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. Trans-Pinocarveol is the (1S,3R,5S)-stereoisomer of pinocarveol. It exists as a pale, clear, yellow oil that is weakly soluble in water (1 g/L). Trans-Pinocarveol is an extremely weak basic (essentially neutral) compound, based on its pKa. It has a herbal, pine, minty or balsamic odor and a comphoreous, pine or fir needle taste. Trans-Pincarveol is found in the essential oils of hop, myssop, grapefruit, rosemary, spearmint and wormwood. It has a role as a GABA(A) modulator (PMID: 24273211), a plant metabolite, a food additive, a cosmetic/fragrance agent and a volatile oil component. With regard to its positive GABA modulating effects, Pinocarveol (along with isopulegol, verbenol, and myrtenol) are particularly potent modifiers of GABA(A) receptor function and this interaction may lead to certain sedative effects found in plants or plant oils that contain this compound (PMID: 24273211). |
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CAS Number | 19894-98-5 |
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Structure | |
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Synonyms | Synonym | Source |
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(-)-trans-2(10)-Pinen-3-ol | HMDB | (1S)-(-)-trans-Pinocarveol | HMDB | (1S,3R,5S)-(-)-2(10)-Pinen-3-ol | HMDB | L-Pinocarveol | HMDB | L-trans-Pinocarveol | HMDB | trans-(-)-Pinocarveol | HMDB | 10-Pinen-3-ol | PhytoBank | 2(10)-Pinen-3-ol | PhytoBank | 6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol | PhytoBank | Pinocarveole | PhytoBank | trans-2(10)-Pinen-3-ol | PhytoBank | (±)-trans-Pinocarveol | PhytoBank | (+)-Pinocarveol | manual | (+)-trans-Pinocarveol | biospider | (1R)-(+)-trans-Pinocarveol | manual | (1R)-trans-Pinocarveol | manual | 2(10)-Pinen-3-ol; (+)-trans-form | db_source | D-trans-Pinocarveol | manual | trans-(+)-Pinocarveol | manual |
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Predicted Properties | |
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Chemical Formula | C10H16O |
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IUPAC name | (1R,3S,5R)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-ol |
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InChI Identifier | InChI=1S/C10H16O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h7-9,11H,1,4-5H2,2-3H3/t7-,8+,9+/m1/s1 |
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InChI Key | LCYXQUJDODZYIJ-VGMNWLOBSA-N |
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Isomeric SMILES | CC1(C)[C@@H]2C[C@H]1C(=C)[C@@H](O)C2 |
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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 bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. |
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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 | Bicyclic monoterpenoids |
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Alternative Parents | |
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Substituents | - Pinane monoterpenoid
- Bicyclic monoterpenoid
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Route of exposure: Biological location: Source: |
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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 78.90%; H 10.59%; O 10.51% | DFC |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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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]25D +60.7 (c, 1.6 in 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 | (+)-trans-Pinocarveol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0019-3900000000-6606ecc9cd06a6da5bd7 | Spectrum | Predicted GC-MS | (+)-trans-Pinocarveol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-05i9-9220000000-95de3481bb916ce84e4f | Spectrum | Predicted GC-MS | (+)-trans-Pinocarveol, 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 | splash10-0f79-0900000000-6ff630040559510e3f1d | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0f79-0900000000-b911719eff5a3760007f | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00kr-0900000000-7dde3d5da047714de193 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0900000000-1384a080edbf08e60385 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0900000000-cce040d437e6c1eee01a | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0f79-0900000000-52674d0954f32b6b3004 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0900000000-c373c9eea3cebf186f53 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0900000000-c373c9eea3cebf186f53 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0udi-0900000000-5f1fa6e5001f7cc95671 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0900000000-88a021c06131e7896a30 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0f79-0900000000-b40ea28a1af5b2c22f29 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-014r-0900000000-50f9a6a23df6edc6a85c | 2021-09-24 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 88302 |
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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 | Not Available |
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CRC / DFC (Dictionary of Food Compounds) ID | JRB55-G:JPV96-B |
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EAFUS ID | Not Available |
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Dr. Duke ID | TRANS-PINOCARVEOL |
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BIGG ID | Not Available |
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KNApSAcK ID | C00000829 |
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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 | Not Available |
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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-malarial | 33281 | An agent that prevents or treats malaria, a disease caused by Plasmodium parasites. It works by targeting the parasite's life cycle, reducing symptoms and preventing transmission. Therapeutically, anti-malarials are used to treat and prevent malaria, as well as to manage related conditions such as babesiosis and toxoplasmosis. | DUKE | Anti plasmodial | 33281 | An agent that inhibits the growth of Plasmodium parasites, reducing malaria symptoms. Therapeutically, it's used to treat and prevent malaria, with key medical applications including prophylaxis and treatment of malaria infections. | 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 | Not Available |
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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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