| Record Information |
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| Version | 2.0 |
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| Created at | 2022-03-17 20:55:56 UTC |
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| Updated at | 2022-03-17 20:55:56 UTC |
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| NP-MRD ID | NP0048404 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Nootkatone |
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| Description | Nookatone, also known as nootkatane, 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. Nookatone is an extremely weak basic (essentially neutral) compound (based on its pKa). Nookatone is a citrus, gardenia, and grapefruit peel tasting compound. Outside of the human body, Nookatone is found, on average, in the highest concentration within a few different foods, such as sweet oranges, mandarin orange (clementine, tangerine), and limes. Nookatone has also been detected, but not quantified in, citrus and lemons. This could make nookatone a potential biomarker for the consumption of these foods. It is also found in Alaska yellow cedar trees and vetiver grass. As a liquid, it is viscous and yellow. In its solid form it is usually found as crystals. It is a sesquiterpene and a ketone. Nootkatone is a natural organic compound and is the most important and expensive aromatic of grapefruit. Nootkatone is typically extracted from grapefruit, but can also be manufactured with genetically modified organisms, or through the chemical or biochemical oxidation of valencene. Nootkatone is found in Alpinia oxyphylla , Artemisia annua , Bupleurum chaishoui, Bupleurum chinense, Bupleurum marginatum var.stenophyllum, Bupleurum scornerifolium, Callitropsis nootkatensis, Chrysanthemum indicum , Citrus aurantium, Citrus paradisi L. , Citrus sinensis, Citrus sinensis L. , Cyperus rotundus, Dendrobium nobile , Vladimiria souliei, Juniperus brevifolia, Juniperus communis , Juniperus oxycedrus , Mandragora autumnalis, Mandragora officinarum, Patrinia heterophylla, Saussurea involucrata, Schisandra chinensis , Teucrium oxylepis, Valeriana jatamansi and Valeriana officinalis . Nootkatone was previously thought to be one of the main chemical components of the smell and flavour of grapefruits. |
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| Structure | CC1CC(=O)C=C2CCC(CC12C)C(C)=C 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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| Synonyms | | Value | 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 |
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| Chemical Formula | C15H22O |
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| Average Mass | 218.3346 Da |
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| Monoisotopic Mass | 218.16707 Da |
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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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| Traditional Name | nootkatone |
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| CAS Registry Number | 4674-50-4 |
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| SMILES | CC1CC(=O)C=C2CCC(CC12C)C(C)=C |
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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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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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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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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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