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 - Experimental |
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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 | |
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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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