Record Information |
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Version | 1.0 |
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Creation date | 2015-05-07 19:56:26 UTC |
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Update date | 2019-11-26 03:21:52 UTC |
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Primary ID | FDB030727 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | cinnamaldehyde |
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Description | Cinnamaldehyde, also known as (E)-3-phenyl-2-propenal or 3-phenylacrylaldehyde, is a member of the class of compounds known as cinnamaldehydes. Cinnamaldehydes are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal. Cinnamaldehyde is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Cinnamaldehyde is a sweet, candy, and cinnamon tasting compound and can be found in a number of food items such as sour cherry, rubus (blackberry, raspberry), horseradish, and sea-buckthornberry, which makes cinnamaldehyde a potential biomarker for the consumption of these food products. Cinnamaldehyde can be found primarily in feces, as well as in human neuron and skin tissues. Cinnamaldehyde exists in all eukaryotes, ranging from yeast to humans. Cinnamaldehyde is a non-carcinogenic (not listed by IARC) potentially toxic compound. Cinnamaldehyde is an organic compound with the formula C6H5CH=CHCHO. Occurring naturally as predominantly the trans (E) isomer, it gives cinnamon its flavor and odor. It is a flavonoid that is naturally synthesized by the shikimate pathway. This pale yellow, viscous liquid occurs in the bark of cinnamon trees and other species of the genus Cinnamomum. The essential oil of cinnamon bark is about 50% cinnamaldehyde . The specific symptoms that can result from cinnamic aldehyde allergy can vary considerably amongst patients from a severe anaphylactic reaction to asthma, abdominal symptoms, eczema or headaches (L2140) (T3DB). |
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CAS Number | 104-55-2 |
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Structure | |
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Synonyms | Synonym | Source |
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(e)-3-Phenyl-2-propenal | ChEBI | (e)-3-Phenyl-propenal | ChEBI | (e)-3-Phenylpropenal | ChEBI | (e)-Cinnamic aldehyde | ChEBI | (e)-Phenylvinyl aldehyde | ChEBI | 3-Phenylacrylaldehyde | ChEBI | trans-Cinnamic aldehyde | ChEBI | (e)-Cinnamaldehyde | HMDB | (2E)-3-Phenyl-2-propenal | HMDB | (2E)-3-Phenylacrylaldehyde | HMDB | 3-Fenylpropenal | HMDB | 3-Phenyl-2-propen-1-al | HMDB | 3-Phenyl-2-propenaldehyde | HMDB | 3-Phenylacrolein | HMDB | 3-Phenylprop-2-enal | HMDB | 3-Phenylpropenal | HMDB | Benzylideneacetaldehyde | HMDB | beta-Phenylcrolein | HMDB | Cinnamal | HMDB | Cinnamic aldehyde | HMDB | Cinnamyl aldehyde | HMDB | Cinnamylaldehyde | HMDB | Cinnemaldehyde | HMDB | trans-3-Phenyl-2-propenal | HMDB | trans-Cinnamaldehyde | HMDB | trans-Cinnamylaldehyde | HMDB | beta-Phenylacrolein | HMDB | Supercinnamaldehyde | HMDB | trans-3-Phenylprop-2-enaldehyde | HMDB | 3-Phenylprop-2-enaldehyde | HMDB | Cinnamic aldehyde, (e)-isomer | HMDB | 2E)-3-Phenyl-2-propenal | PhytoBank | (E)-3-Phenylacrolein | PhytoBank | (E)-3-Phenylprop-2-en-1-al | PhytoBank | (E)-3-Phenylprop-2-enal | PhytoBank | (E)-3-Phenylprop-2-enone | PhytoBank | E-Cinnamyl aldehyde | PhytoBank | trans-3-Phenylpropenal | PhytoBank | trans-Benzenepropenal | PhytoBank | 3-Phenyl-2-propenal | PhytoBank | 3-Phenyl-2-propene-1-al | PhytoBank |
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Predicted Properties | |
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Chemical Formula | C9H8O |
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IUPAC name | (2E)-3-phenylprop-2-enal |
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InChI Identifier | InChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4+ |
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InChI Key | KJPRLNWUNMBNBZ-QPJJXVBHSA-N |
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Isomeric SMILES | [H]C(=O)\C=C\C1=CC=CC=C1 |
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Average Molecular Weight | 132.1592 |
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Monoisotopic Molecular Weight | 132.057514878 |
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Classification |
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Description | Belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Cinnamaldehydes |
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Sub Class | Not Available |
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Direct Parent | Cinnamaldehydes |
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Alternative Parents | |
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Substituents | - Cinnamaldehyde
- Styrene
- Benzenoid
- Monocyclic benzene moiety
- Enal
- Alpha,beta-unsaturated aldehyde
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aldehyde
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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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 | Not Available | |
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Melting Point | Not Available | |
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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 | 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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GC-MS | (E)-3-Phenyl-2-propenal, non-derivatized, GC-MS Spectrum | splash10-0059-3900000000-52db83b595237437ab08 | Spectrum | GC-MS | (E)-3-Phenyl-2-propenal, non-derivatized, GC-MS Spectrum | splash10-0f89-5900000000-540c43f6893b35e8a105 | Spectrum | GC-MS | (E)-3-Phenyl-2-propenal, non-derivatized, GC-MS Spectrum | splash10-0f89-5900000000-482f8b5c30c53689d8eb | Spectrum | GC-MS | (E)-3-Phenyl-2-propenal, non-derivatized, GC-MS Spectrum | splash10-001i-3900000000-9d274f5e3981ab662650 | Spectrum | GC-MS | (E)-3-Phenyl-2-propenal, non-derivatized, GC-MS Spectrum | splash10-001i-0900000000-4f0ad7748ac21b7320c9 | Spectrum | GC-MS | (E)-3-Phenyl-2-propenal, non-derivatized, GC-MS Spectrum | splash10-0f89-6900000000-ecaba4b9d657020c3f4c | Spectrum | GC-MS | (E)-3-Phenyl-2-propenal, non-derivatized, GC-MS Spectrum | splash10-001i-0900000000-c02b7869dea8f1113cb4 | Spectrum | GC-MS | (E)-3-Phenyl-2-propenal, non-derivatized, GC-MS Spectrum | splash10-001i-2900000000-d89aa99ef7a6ae16b942 | Spectrum | GC-MS | (E)-3-Phenyl-2-propenal, non-derivatized, GC-MS Spectrum | splash10-0ugi-8900000000-14f14e29c81360ebdd4b | Spectrum | GC-MS | (E)-3-Phenyl-2-propenal, non-derivatized, GC-MS Spectrum | splash10-0059-3900000000-52db83b595237437ab08 | Spectrum | Predicted GC-MS | (E)-3-Phenyl-2-propenal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0f89-4900000000-e9eb0053986096f21c83 | Spectrum | Predicted GC-MS | (E)-3-Phenyl-2-propenal, 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) | splash10-0a59-5900000000-a125425df0f09bb01129 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-056r-9300000000-043ea317ed08a1cbacfb | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-004i-9000000000-39ab07ef5d737e851671 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive | splash10-0f89-5900000000-f27dd11a8900d729bd19 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive | splash10-0f89-5900000000-4e11cf955911f9ca7da2 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (SHIMADZU QP-1000) , Positive | splash10-001i-3900000000-9d274f5e3981ab662650 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (SHIMADZU QP-1000) , Positive | splash10-001i-0900000000-4f0ad7748ac21b7320c9 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive | splash10-0f89-6900000000-e363e674a4ec6e092f26 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - CI-B (HITACHI M-80) , Positive | splash10-001i-0900000000-c02b7869dea8f1113cb4 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive | splash10-001i-2900000000-7339e3ff66ab63ba3409 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive | splash10-0ugi-8900000000-1b72d0d216af15365444 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-067i-2900000000-76d2db81f3822a698f0a | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-067i-2900000000-76d2db81f3822a698f0a | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-1900000000-4b1b083c8fdb2a27206b | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00lr-2900000000-eee6045375789bd7b511 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0f6x-9400000000-ffef407879854d06bd7e | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0900000000-074611feed644fd89c07 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0900000000-cbf5bec188b738c514af | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-01p6-9600000000-5eb930cf87b199a5f449 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0900000000-827b27666b5028c8cf77 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0900000000-138b8c24fd394024a31a | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9200000000-93f143b30bbb2b4ff778 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00lu-2900000000-eda42d3592c23cd1e4bd | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-5900000000-5757a78bf103c73ab434 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fvi-9300000000-8784eab3c86fc7a1a721 | 2021-09-23 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Methanol, 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 | 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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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 | 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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