Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:11:18 UTC |
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Update date | 2019-11-26 03:10:09 UTC |
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Primary ID | FDB014484 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | alpha-Ionone |
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Description | Alpha-ionone, also known as (E)-α-ionone or alpha-cyclocitrylideneacetone, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Alpha-ionone is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Alpha-ionone is a sweet, floral, and fruity tasting compound and can be found in a number of food items such as tea, wild carrot, wild celery, and ginkgo nuts, which makes alpha-ionone a potential biomarker for the consumption of these food products. Alpha-ionone can be found primarily in saliva. Alpha-ionone exists in all eukaryotes, ranging from yeast to humans. Alpha-ionone is a non-carcinogenic (not listed by IARC) potentially toxic compound. |
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CAS Number | 127-41-3 |
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Structure | |
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Synonyms | Synonym | Source |
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(e)-alpha-Ionone | ChEBI | alpha-(e)-Ionone | ChEBI | alpha-Cyclocitrylideneacetone | ChEBI | alpha-Ionon | ChEBI | trans-alpha-Ionone | ChEBI | (e)-a-Ionone | Generator | (e)-Α-ionone | Generator | a-(e)-Ionone | Generator | Α-(e)-ionone | Generator | a-Cyclocitrylideneacetone | Generator | Α-cyclocitrylideneacetone | Generator | a-Ionon | Generator | Α-ionon | Generator | trans-a-Ionone | Generator | trans-Α-ionone | Generator | a-Ionone | Generator | Α-ionone | Generator | (3E)-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-ON | HMDB | alpha-Ionone, (e)-isomer | MeSH | alpha-Ionone, (e)-(+-)-isomer | MeSH | alpha-Ionone, (+)-iosmer | MeSH | (±)-alpha-Ionone | manual | (±)-trans-alpha-Ionone | manual | (3E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one | manual | (5E)-Ionone | manual | (E)-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one | manual | (E)-alpha-Ionone | manual | α-ionone | biospider | 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (3E)- | manual | Alpha-ionone | biospider | FEMA 2594 | db_source | Ionone, alpha- | biospider |
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Predicted Properties | |
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Chemical Formula | C13H20O |
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IUPAC name | (3E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one |
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InChI Identifier | InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h6-8,12H,5,9H2,1-4H3/b8-7+ |
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InChI Key | UZFLPKAIBPNNCA-BQYQJAHWSA-N |
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Isomeric SMILES | CC(=O)\C=C\C1C(C)=CCCC1(C)C |
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Average Molecular Weight | 192.2973 |
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Monoisotopic Molecular Weight | 192.151415262 |
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Classification |
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Description | Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. |
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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 | Sesquiterpenoids |
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Alternative Parents | |
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Substituents | - Cyclofarsesane sesquiterpenoid
- Megastigmane sesquiterpenoid
- Sesquiterpenoid
- Ionone derivative
- Alpha,beta-unsaturated ketone
- Enone
- Acryloyl-group
- 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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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: Industrial application: |
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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 81.20%; H 10.48%; O 8.32% | DFC |
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Melting Point | < 25 oC | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 0.106 mg/mL at 25 oC | ETZWEILER,F et al. (1995) |
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Experimental logP | 3.85 | GRIFFIN,S ET AL. (1999) |
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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 | Not Available | |
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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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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0006-9800000000-d19fa6227b12fe21dbc3 | 2014-10-20 | View Spectrum | Predicted GC-MS | alpha-Ionone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-004i-4900000000-acff00e4fe614e1e5bc8 | Spectrum | Predicted GC-MS | alpha-Ionone, 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 | splash10-002f-0900000000-0d1ee7a07c25e0eb379a | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004u-3900000000-122599cd5a3606da3858 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-014i-9400000000-5525adff7c75947a3830 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0900000000-86ad4191ecec06d667eb | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-0900000000-81ca79f706995e1f2313 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0aed-2900000000-e754146e5b21f942f91e | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-006x-0900000000-dca766c12d151f3d74b1 | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05fu-8900000000-26ead371c8e940e8859e | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05mo-9600000000-ad142c26c199a3741a02 | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0900000000-14436e4d9ff8d032db54 | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0900000000-7cd7cf4235cb00fbc0b5 | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0kmj-3900000000-b5da866d6db21994e86c | 2021-10-12 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | | 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 | C12286 |
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Pubchem Compound ID | 5282108 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 32319 |
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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 | JRF23-P:JRF23-P |
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EAFUS ID | 1805 |
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Dr. Duke ID | ALPHA-IONONE |
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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 | 127-41-3 |
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GoodScent ID | rw1011951 |
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SuperScent ID | 5282108 |
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Wikipedia ID | Ionone |
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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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Allergenic | 50904 | A substance that triggers an immune response, causing allergic reactions. Its biological role is to stimulate the immune system, but it has no therapeutic applications. Key medical uses include diagnosing allergies and developing immunotherapies to desensitize patients to specific allergens, reducing the risk of severe reactions. | DUKE | Cytochrome-P450-1A inducer | | An agent that stimulates cytochrome-P450-1A enzyme activity, enhancing phase I metabolism of xenobiotics and drugs, and activating aromatic hydrocarbons. Therapeutically, it aids in detoxification and is used in managing conditions like cancer and toxic exposures. | DUKE | Cytochrome-P450-2B inducer | | An agent that stimulates cytochrome-P450-2B activity, enhancing drug metabolism, particularly for anti-cancer drugs like cyclophosphamide, and lipid synthesis, with therapeutic applications in cancer treatment and potentially managing lipid disorders. | DUKE | Perfume | 48318 | A fragrant substance with a biological role in attracting and repelling, having therapeutic applications in aromatherapy for mood enhancement and stress relief. Key medical uses include anxiety reduction, mood elevation, and pain management, with some fragrances exhibiting anti-anxiety and anti-depressant properties. | DUKE | Tremorigenic | | An agent that induces tremors, causing involuntary muscle contractions and relaxation, often used in research to study movement disorders, with potential therapeutic applications in neurology and psychiatry, particularly in managing conditions like Parkinson's disease and essential tremor. | 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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wood |
- 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
| violet |
- 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
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| raspberry |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| sweet |
- 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.
| floral |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| orris |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| tropical |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| fruity |
- 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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