Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:11:28 UTC |
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Update date | 2019-11-26 03:10:47 UTC |
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Primary ID | FDB014799 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Nootkatone |
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Description | Nootkatone belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Based on a literature review a significant number of articles have been published on Nootkatone. |
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CAS Number | 4674-50-4 |
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Structure | |
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Synonyms | Synonym | Source |
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(+)-5,6-Dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one | HMDB | 4BetaH,5alpha-eremophila-1(10),11-dien-2-one | HMDB | 4BetaH,5alpha-eremorphila-1(10)11-dien-2-one | HMDB | Nootkatane | HMDB | Nootkatone, (4R-(4alpha,4aalpha,6beta))-isomer | MeSH | (+)-5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one | biospider | (+)-Nootkatone | biospider | 4βH,5α-Eremophila-1(10),11-dien-2-one | biospider | 4βH,5α-Eremorphila-1(10)11-dien-2-one | biospider | 4betaH,5alpha-Eremophila-1(10),11-dien-2-one | biospider | 4betaH,5alpha-Eremorphila-1(10)11-dien-2-one | biospider | 5,6-Dimethyl-8-isopropenylbicyclo(4.4.0)dec-1-en-3-one | biospider | FEMA 3166 | db_source | Nootkanone | biospider | Nootkatone | db_source |
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Predicted Properties | |
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Chemical Formula | C15H22O |
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IUPAC name | 4,4a-dimethyl-6-(prop-1-en-2-yl)-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-one |
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InChI Identifier | InChI=1S/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12H,1,5-7,9H2,2-4H3 |
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InChI Key | WTOYNNBCKUYIKC-UHFFFAOYSA-N |
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Isomeric SMILES | CC1CC(=O)C=C2CCC(CC12C)C(C)=C |
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Average Molecular Weight | 218.3346 |
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Monoisotopic Molecular Weight | 218.167065326 |
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Classification |
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Description | Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. |
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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 | Sesquiterpenoids |
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Direct Parent | Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids |
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Alternative Parents | |
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Substituents | - Eremophilane sesquiterpenoid
- Cyclohexenone
- Cyclic ketone
- Ketone
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- 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 | 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 82.52%; H 10.16%; O 7.33% | DFC |
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Melting Point | Mp 36-37° | DFC |
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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]D +195.5 (c, 1.5 in CHCl3) | 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 | Nootkatone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0fbi-1910000000-b45e411b466c6a4f701e | Spectrum | Predicted GC-MS | Nootkatone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Nootkatone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Nootkatone, 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 | splash10-014i-0190000000-c24752b1318a3a711643 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-017i-2930000000-22f4dc6376ca69ed6b2a | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0gb9-9700000000-fc684e09e444485e471b | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0090000000-985cf431add494d4b1ca | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0090000000-9295b5b0acc45864f5c2 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0f79-0930000000-b1395e8a051a4ce6d609 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0090000000-868e2fb00a2cfbf6c529 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0090000000-868e2fb00a2cfbf6c529 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-0890000000-6acaaae614c8694f91a8 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-016r-0890000000-0186d1632d3974cab9e4 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05br-1910000000-7e41e7df099107da9183 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9200000000-451c0b277f60bba512c6 | 2021-09-22 | 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 | 20797 |
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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 | JVX45-L:JVX45-L |
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EAFUS ID | 2720 |
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Dr. Duke ID | NOOTKATONE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00016987 |
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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 | 4674-50-4 |
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GoodScent ID | rw1005641 |
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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 ulcer | 49201 | An agent that reduces stomach acid and protects the mucous lining, preventing ulcer formation. It is used to treat conditions like gastroesophageal reflux disease (GERD), peptic ulcers, and Zollinger-Ellison syndrome, promoting healing and relieving symptoms. | DUKE | Name | 48318 | flavor | DUKE | Perfumery | 48318 | The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties. | 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 | Flavor | Citations |
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grapefruit |
- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
| grapefruit peel |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| citrus |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| gardenia |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| woody |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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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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