Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2006-08-12 20:46:08 UTC |
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Update Date | 2023-02-21 17:16:40 UTC |
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HMDB ID | HMDB0003441 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Cinnamaldehyde |
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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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Structure | InChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4+ |
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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 Weight | 132.1592 |
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Monoisotopic Molecular Weight | 132.057514878 |
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IUPAC Name | (2E)-3-phenylprop-2-enal |
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Traditional Name | cinnamal |
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CAS Registry Number | 104-55-2 |
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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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Ontology |
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Physiological effect | |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Liquid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | -7.5 °C | Not Available | Boiling Point | 248.00 °C. @ 760.00 mm Hg | The Good Scents Company Information System | Water Solubility | 1.42 mg/mL at 25 °C | Not Available | LogP | 1.90 | HANSCH,C ET AL. (1995) |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Cinnamaldehyde GC-MS (Non-derivatized) | splash10-0059-3900000000-52db83b595237437ab08 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Cinnamaldehyde EI-B (Non-derivatized) | splash10-0f89-5900000000-540c43f6893b35e8a105 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Cinnamaldehyde EI-B (Non-derivatized) | splash10-0f89-5900000000-482f8b5c30c53689d8eb | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Cinnamaldehyde EI-B (Non-derivatized) | splash10-001i-3900000000-9d274f5e3981ab662650 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Cinnamaldehyde EI-B (Non-derivatized) | splash10-001i-0900000000-4f0ad7748ac21b7320c9 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Cinnamaldehyde EI-B (Non-derivatized) | splash10-0f89-6900000000-ecaba4b9d657020c3f4c | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Cinnamaldehyde CI-B (Non-derivatized) | splash10-001i-0900000000-c02b7869dea8f1113cb4 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Cinnamaldehyde EI-B (Non-derivatized) | splash10-001i-2900000000-d89aa99ef7a6ae16b942 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Cinnamaldehyde EI-B (Non-derivatized) | splash10-0ugi-8900000000-14f14e29c81360ebdd4b | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Cinnamaldehyde GC-MS (Non-derivatized) | splash10-0059-3900000000-52db83b595237437ab08 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cinnamaldehyde GC-MS (Non-derivatized) - 70eV, Positive | splash10-0f89-4900000000-e9eb0053986096f21c83 | 2016-09-22 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cinnamaldehyde GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Cinnamaldehyde Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-0a59-5900000000-a125425df0f09bb01129 | 2012-07-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cinnamaldehyde Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-056r-9300000000-043ea317ed08a1cbacfb | 2012-07-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cinnamaldehyde Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-004i-9000000000-39ab07ef5d737e851671 | 2012-07-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cinnamaldehyde EI-B (HITACHI RMU-7M) , Positive-QTOF | splash10-0f89-5900000000-f27dd11a8900d729bd19 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cinnamaldehyde EI-B (JEOL JMS-D-3000) , Positive-QTOF | splash10-0f89-5900000000-4e11cf955911f9ca7da2 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cinnamaldehyde EI-B (SHIMADZU QP-1000) , Positive-QTOF | splash10-001i-3900000000-9d274f5e3981ab662650 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cinnamaldehyde EI-B (SHIMADZU QP-1000) , Positive-QTOF | splash10-001i-0900000000-4f0ad7748ac21b7320c9 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cinnamaldehyde EI-B (HITACHI RMU-6M) , Positive-QTOF | splash10-0f89-6900000000-e363e674a4ec6e092f26 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cinnamaldehyde CI-B (HITACHI M-80) , Positive-QTOF | splash10-001i-0900000000-c02b7869dea8f1113cb4 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cinnamaldehyde EI-B (HITACHI RMU-6M) , Positive-QTOF | splash10-001i-2900000000-7339e3ff66ab63ba3409 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cinnamaldehyde EI-B (HITACHI M-80B) , Positive-QTOF | splash10-0ugi-8900000000-1b72d0d216af15365444 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cinnamaldehyde LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF | splash10-067i-2900000000-76d2db81f3822a698f0a | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cinnamaldehyde LC-ESI-QTOF , positive-QTOF | splash10-067i-2900000000-76d2db81f3822a698f0a | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cinnamaldehyde 10V, Positive-QTOF | splash10-001i-1900000000-4b1b083c8fdb2a27206b | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cinnamaldehyde 20V, Positive-QTOF | splash10-00lr-2900000000-eee6045375789bd7b511 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cinnamaldehyde 40V, Positive-QTOF | splash10-0f6x-9400000000-ffef407879854d06bd7e | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cinnamaldehyde 10V, Negative-QTOF | splash10-001i-0900000000-074611feed644fd89c07 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cinnamaldehyde 20V, Negative-QTOF | splash10-001i-0900000000-cbf5bec188b738c514af | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cinnamaldehyde 40V, Negative-QTOF | splash10-01p6-9600000000-5eb930cf87b199a5f449 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cinnamaldehyde 10V, Negative-QTOF | splash10-0udi-0900000000-827b27666b5028c8cf77 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cinnamaldehyde 20V, Negative-QTOF | splash10-0udi-0900000000-138b8c24fd394024a31a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cinnamaldehyde 40V, Negative-QTOF | splash10-004i-9200000000-93f143b30bbb2b4ff778 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cinnamaldehyde 10V, Positive-QTOF | splash10-00lu-2900000000-eda42d3592c23cd1e4bd | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cinnamaldehyde 20V, Positive-QTOF | splash10-0udi-5900000000-5757a78bf103c73ab434 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cinnamaldehyde 40V, Positive-QTOF | splash10-0fvi-9300000000-8784eab3c86fc7a1a721 | 2021-09-23 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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General References | - 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. [PubMed:15046718 ]
- 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. [PubMed:6334604 ]
- 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. [PubMed:11042091 ]
- 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. [PubMed:11486835 ]
- 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. [PubMed:12582388 ]
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