Record Information |
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Version | 1.0 |
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Creation Date | 2014-10-14 21:19:45 UTC |
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Update Date | 2016-11-09 01:09:15 UTC |
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Accession Number | CHEM003939 |
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Identification |
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Common Name | Cinnamaldehyde |
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Class | Small Molecule |
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Description | Cinnamaldehyde is the aldehyde that gives cinnamon its flavor and odor. Cinnamaldehyde occurs naturally in the bark of cinnamon trees and other species of the genus Cinnamomum like camphor and cassia. These trees are the natural source of cinnamon, and the essential oil of cinnamon bark is about 90% cinnamaldehyde. Cinnamaldehyde is also used as a fungicide. Proven effective on over 40 different crops, cinnamaldehyde is typically applied to the root systems of plants. Its low toxicity and well-known properties make it ideal for agriculture. To a lesser extent, cinnamaldehyde is an effective insecticide, and its scent is also known to repel animals like cats and dogs. Cinnamaldehyde is also known as a corrosion inhibitor for steel and other ferrous alloys in corrosive fluids. It can be used in combination with additional components such as dispersing agents, solvents and other surfactants. Concentrated cinnamaldehyde is a skin irritant, and the chemical is toxic in large doses, but no agencies suspect the compound is a carcinogen or poses a long-term health hazard. Most cinnamaldehyde is excreted in urine as cinnamic acid, an oxidized form of cinnamaldehyde. |
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Contaminant Sources | - EAFUS Chemicals
- FooDB Chemicals
- HMDB Contaminants - Feces
- HPV EPA Chemicals
- STOFF IDENT Compounds
- T3DB toxins
- ToxCast & Tox21 Chemicals
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Contaminant Type | - Food Toxin
- Industrial/Workplace Toxin
- Metabolite
- Natural Compound
- Pesticide
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Chemical Structure | |
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Synonyms | Value | 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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Chemical Formula | C9H8O |
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Average Molecular Mass | 132.159 g/mol |
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Monoisotopic Mass | 132.058 g/mol |
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CAS Registry Number | 104-55-2 |
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IUPAC Name | (2E)-3-phenylprop-2-enal |
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Traditional Name | cinnamal |
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SMILES | O=C\C=C\C1=CC=CC=C1 |
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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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Chemical Taxonomy |
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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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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Liquid |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | -7.5 °C | Boiling Point | 248 C (478 F; 521 K) | Solubility | 1.42 mg/mL at 25 °C |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-MS | splash10-0059-3900000000-52db83b595237437ab08 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS | splash10-0f89-4900000000-e9eb0053986096f21c83 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B | splash10-0f89-5900000000-540c43f6893b35e8a105 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B | splash10-0f89-5900000000-482f8b5c30c53689d8eb | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B | splash10-001i-3900000000-9d274f5e3981ab662650 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B | splash10-001i-0900000000-4f0ad7748ac21b7320c9 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B | splash10-0f89-6900000000-ecaba4b9d657020c3f4c | View in MoNA |
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GC-MS | GC-MS Spectrum - CI-B | splash10-001i-0900000000-c02b7869dea8f1113cb4 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B | splash10-001i-2900000000-d89aa99ef7a6ae16b942 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B | splash10-0ugi-8900000000-14f14e29c81360ebdd4b | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS | splash10-0059-3900000000-52db83b595237437ab08 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0a59-5900000000-a125425df0f09bb01129 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-056r-9300000000-043ea317ed08a1cbacfb | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-004i-9000000000-39ab07ef5d737e851671 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive | splash10-0f89-5900000000-f27dd11a8900d729bd19 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive | splash10-0f89-5900000000-4e11cf955911f9ca7da2 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - EI-B (SHIMADZU QP-1000) , Positive | splash10-001i-3900000000-9d274f5e3981ab662650 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - EI-B (SHIMADZU QP-1000) , Positive | splash10-001i-0900000000-4f0ad7748ac21b7320c9 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive | splash10-0f89-6900000000-e363e674a4ec6e092f26 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - CI-B (HITACHI M-80) , Positive | splash10-001i-0900000000-c02b7869dea8f1113cb4 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive | splash10-001i-2900000000-7339e3ff66ab63ba3409 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive | splash10-0ugi-8900000000-1b72d0d216af15365444 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-067i-2900000000-76d2db81f3822a698f0a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-067i-2900000000-76d2db81f3822a698f0a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-1900000000-4b1b083c8fdb2a27206b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00lr-2900000000-eee6045375789bd7b511 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0f6x-9400000000-ffef407879854d06bd7e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0900000000-074611feed644fd89c07 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0900000000-cbf5bec188b738c514af | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-01p6-9600000000-5eb930cf87b199a5f449 | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available |
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Toxicity Profile |
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Route of Exposure | Inhalation; dermal; ingestion |
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Mechanism of Toxicity | Cinnamaldehyde is an allergen. The physiologic effect of cinnamaldehyde is by means of increased histamine release and cell-mediated immunity. |
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Metabolism | Cinnamaldehyde is converted to cinnamoyl-CoA by cinnamoyl-CoA reductase. |
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Toxicity Values | LD50: 3400 mg/kg (rat, oral) |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Allergic reaction. |
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Symptoms | 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. (6) |
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Treatment | Not Available |
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Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | HMDB0003441 |
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FooDB ID | FDB030727 |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | C00035187 |
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BiGG ID | Not Available |
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BioCyc ID | Not Available |
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METLIN ID | 6931 |
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PDB ID | Not Available |
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Wikipedia Link | Cinnamaldehyde |
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Chemspider ID | 553117 |
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ChEBI ID | 16731 |
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PubChem Compound ID | 637511 |
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Kegg Compound ID | C00903 |
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YMDB ID | YMDB01654 |
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ECMDB ID | Not Available |
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References |
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Synthesis Reference | Liu, Xue-mei. Synthesis of cinnamaldehyde. Qufu Shifan Daxue Xuebao, Ziran Kexueban (2005), 31(2), 96-98. |
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MSDS | Not Available |
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General References | 1. Liu, Xue-mei. Synthesis of cinnamaldehyde. Qufu Shifan Daxue Xuebao, Ziran Kexueban (2005), 31(2), 96-98. | 2. Muller G, Biering A, Graubaum K, Jeschkeit H, Neubert K, Kleine R, Klapperstuck M: [The PABA test]. Dtsch Z Verdau Stoffwechselkr. 1984;44(5):219-31. | 3. Smith CK, Moore CA, Elahi EN, Smart AT, Hotchkiss SA: Human skin absorption and metabolism of the contact allergens, cinnamic aldehyde, and cinnamic alcohol. Toxicol Appl Pharmacol. 2000 Nov 1;168(3):189-99. | 4. Bandell M, Story GM, Hwang SW, Viswanath V, Eid SR, Petrus MJ, Earley TJ, Patapoutian A: Noxious cold ion channel TRPA1 is activated by pungent compounds and bradykinin. Neuron. 2004 Mar 25;41(6):849-57. | 5. Smith CK, Cheung C, Elahi EN, Hotchkiss SA: High-performance liquid chromatography method for the quantification of non-radiolabelled cinnamic compounds in analytes derived from human skin absorption and metabolism experiments. J Chromatogr B Biomed Sci Appl. 2001 Jul 15;758(2):249-64. | 6. Bruze M, Johansen JD, Andersen KE, Frosch P, Lepoittevin JP, Rastogi S, Wakelin S, White I, Menne T: Deodorants: an experimental provocation study with cinnamic aldehyde. J Am Acad Dermatol. 2003 Feb;48(2):194-200. | 7. https://www.ncbi.nlm.nih.gov/pubmed/?term=11975643 | 8. https://www.ncbi.nlm.nih.gov/pubmed/?term=17140783 | 9. https://www.ncbi.nlm.nih.gov/pubmed/?term=17662960 | 10. https://www.ncbi.nlm.nih.gov/pubmed/?term=18218683 | 11. https://www.ncbi.nlm.nih.gov/pubmed/?term=19845671 | 12. https://www.ncbi.nlm.nih.gov/pubmed/?term=20431333 | 13. https://www.ncbi.nlm.nih.gov/pubmed/?term=20955755 | 14. https://www.ncbi.nlm.nih.gov/pubmed/?term=21266172 | 15. https://www.ncbi.nlm.nih.gov/pubmed/?term=21388814 | 16. https://www.ncbi.nlm.nih.gov/pubmed/?term=21394803 | 17. https://www.ncbi.nlm.nih.gov/pubmed/?term=21466812 | 18. https://www.ncbi.nlm.nih.gov/pubmed/?term=21469739 | 19. https://www.ncbi.nlm.nih.gov/pubmed/?term=21517069 | 20. https://www.ncbi.nlm.nih.gov/pubmed/?term=21603596 | 21. https://www.ncbi.nlm.nih.gov/pubmed/?term=21708228 | 22. https://www.ncbi.nlm.nih.gov/pubmed/?term=21767279 | 23. https://www.ncbi.nlm.nih.gov/pubmed/?term=21788726 | 24. https://www.ncbi.nlm.nih.gov/pubmed/?term=29079364 |
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