Record Information |
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Version | 1.0 |
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Creation date | 2020-04-21 17:18:42 UTC |
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Update date | 2020-09-17 15:31:20 UTC |
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Primary ID | FDB112393 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Eucalyptol |
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Description | 1,8-Cineole also known as Eucalyptol, belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-membered saturated aliphatic heterocycle, composed of one oxygen atom and five carbon atoms. Eucalyptol is an organic compound that is a colourless liquid. It is a cyclic ether and a monoterpenoid. 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 the plastids. 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. Eucalyptol is a natural constituent of a number of aromatic plants and their essential oil fractions. Eucalyptus oil is the oil extracted from the leaves of various Eucalyptus species. Eucalyptol oil is used for its aromatic properties and as an ingredient in pharmaceutical and industrial applications. Cineole-based eucalyptus oil is used as a flavouring at low levels (0.002%) in various products, including baked goods, confectionery, meat products, and beverages. Eucalyptol was given GRAS (Generally Recognized as Safe) status by the Flavor and Extract Manufacturer's Association FEMA in 1965 and is approved by the Food and Drug Administration for food use. 1,8-Dihydroxy-10-carboxy-p-menthane, 2-hydroxy-cineole, and 3-hydroxy-cineole are the main metabolites of eucalyptol. Toxicological data available on eucalyptol is rather limited. Following accidental exposure, death was reported in two cases after ingestion of 3.5-5 mL of essential eucalyptus oil, but a number of recoveries have also been described for much higher amounts of oil. In a 1994 report released by five top cigarette companies, eucalyptol was listed as one of the 599 additives to cigarettes. It is added to improve the flavour (PMID: 12048025). Eucalyptol is found in many foods, some of which are common thyme, caraway, sunflower, and pot marjoram. |
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CAS Number | Not Available |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C10H18O |
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IUPAC name | (1s,4s)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane |
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InChI Identifier | InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3/t8-,10+ |
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InChI Key | WEEGYLXZBRQIMU-WAAGHKOSSA-N |
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Isomeric SMILES | C[C@@]12CC[C@@H](CC1)C(C)(C)O2 |
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Average Molecular Weight | 154.2493 |
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Monoisotopic Molecular Weight | 154.135765198 |
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Classification |
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Description | Belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Oxanes |
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Sub Class | Not Available |
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Direct Parent | Oxanes |
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Alternative Parents | |
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Substituents | - Oxane
- Oxacycle
- Ether
- Dialkyl ether
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | |
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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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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0536-9200000000-aa52695ff4a2c1313e0b | 2015-03-01 | View Spectrum | Predicted GC-MS | Eucalyptol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0f79-3900000000-207d29106cfe3c54c018 | Spectrum | Predicted GC-MS | Eucalyptol, 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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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-001i-9500000000-9dc534a13d795eb1b96c | 2020-03-10 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-001i-9000000000-c05885d0e60c65af2adf | 2020-03-10 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-003u-9000000000-217a9576a252e6456825 | 2020-03-10 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0900000000-87fbd679809c90a3eb19 | 2017-07-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-0900000000-aa8e8e9cd53dad3b120e | 2017-07-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052r-0900000000-5296316e735fc49999bf | 2017-07-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0900000000-99f5c9faaf8cf2b40394 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0900000000-99f5c9faaf8cf2b40394 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0f79-0900000000-da51d6a18dbcbda3b168 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0900000000-d2363ae8d4dbdcccda80 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0900000000-d2363ae8d4dbdcccda80 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0udi-0900000000-9ea4da9bfdad90f3be7e | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0900000000-085a10049717ea8e20df | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-0900000000-085a10049717ea8e20df | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0pbi-0900000000-5cb534f49edce4797f2c | 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, 25.16 MHz, CDCl3, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | | Spectrum |
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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 | Not Available |
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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 | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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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 | 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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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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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 | |
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