Record Information |
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Version | 2.0 |
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Creation Date | 2012-08-09 09:16:11 -0600 |
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Update Date | 2015-09-13 15:15:33 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | Cinnamic acid |
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Description | Cinnamic acid has the formula C6H5CHCHCOOH and is an odorless white crystalline acid, which is slightly soluble in water. It has a melting point of 133 degree centigrade and a boiling point of 300 degree centigrade. It is an intermediate in the degradation of aromatic compounds in E. coli and is a substrate for several dioxygenases. |
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Structure | |
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Synonyms: | - (E)-3-phenyl-2-propenoate
- (E)-3-phenyl-2-propenoic acid
- 3-Phenyl-2-propenoate
- 3-Phenyl-2-propenoic acid
- 3-phenyl-acrylate
- 3-phenyl-acrylic acid
- 3-Phenylacrylate
- 3-Phenylacrylic acid
- 3-phenylpropenoate
- 3-phenylpropenoic acid
- b-Phenylacrylate
- b-Phenylacrylic acid
- Benzenepropenoate
- Benzenepropenoic acid
- Benzylideneacetate
- Benzylideneacetic acid
- beta-Phenylacrylate
- Beta-Phenylacrylic acid
- Cinnamate
- Cinnamylate
- Cinnamylic acid
- Phenylacrylate
- Phenylacrylic acid
- β-Phenylacrylate
- β-Phenylacrylic acid
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Chemical Formula: | C9H8O2 |
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Weight: | Average: 148.1586 Monoisotopic: 148.0524295 |
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InChI Key: | WBYWAXJHAXSJNI-SREVYHEPSA-N |
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InChI: | InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6- |
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CAS number: | 621-82-9 |
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IUPAC Name: | (2Z)-3-phenylprop-2-enoic acid |
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Traditional IUPAC Name: | cis-cinnamic acid |
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SMILES: | OC(=O)\C=C/C1=CC=CC=C1 |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Cinnamic acids and derivatives |
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Sub Class | Cinnamic acids |
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Direct Parent | Cinnamic acids |
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Alternative Parents | |
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Substituents | - Cinnamic acid
- Styrene
- Benzenoid
- Monocyclic benzene moiety
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State: | Solid |
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Charge: | -1 |
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Melting point: | 132-135 °C |
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Experimental Properties: | Property | Value | Source |
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Water Solubility: | 0.57 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] | PhysProp | LogP: | 2.13 [HANSCH,C ET AL. (1995)] | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | |
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SMPDB Pathways: | Not Available |
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KEGG Pathways: | Not Available |
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EcoCyc Pathways: | Not Available |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0udi-1900000000-f00ddafc38ffb949fd1f | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0fl0-7930000000-f3ac0a061fb66ec84b5d | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated) | splash10-066s-4900000000-f4bfd33daf0938375a0d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated) | splash10-0udi-0900000000-d93fb5a9c15682c1e6ee | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated) | splash10-004i-9000000000-9be1ef1ea4500691cb22 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-b4400af8b5aad0d8d323 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0fb9-9700000000-7d7dbe711d881767830e | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0900000000-20d69cc859de39f18004 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-1357b63887db6df1be7a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0f89-0900000000-b8c6ecaf3fa85d1487a6 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-7900000000-0805b8dbbbd2777f28c4 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-6e7b31576f8ffd356252 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0f92-0900000000-c5fb484b178fce86b596 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0fb9-1900000000-36b618a3b50dc51ff302 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0900000000-5a19a7768eb87376d23c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0900000000-138b8c24fd394024a31a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9200000000-dd9a9ae0caad4bca05c8 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-530f30f323b6e6a53394 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0900000000-648b395c048d84ce7d9a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fb9-9600000000-cb54ab97d7414eccc874 | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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References: | - Kukongviriyapan V, Phromsopha N, Tassaneeyakul W, Kukongviriyapan U, Sripa B, Hahnvajanawong V, Bhudhisawasdi V: Inhibitory effects of polyphenolic compounds on human arylamine N-acetyltransferase 1 and 2. Xenobiotica. 2006 Jan;36(1):15-28. Pubmed: 16507510
- Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
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Synthesis Reference: | An, Hong; He, Xifeng; Fu, Jing. Synthesis of cinnamic acid. Huagong Shikan (2005), 19(7), 32-33, 41. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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Links |
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External Links: | |
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