Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:19 UTC |
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Update date | 2019-11-26 03:07:24 UTC |
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Primary ID | FDB012698 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | cis-Cinnamic acid |
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Description | Cinnamic acid, also known as (Z)-cinnamate or 3-phenyl-acrylate, 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. Cinnamic acid exists in all living organisms, ranging from bacteria to humans. Cinnamic acid has been detected, but not quantified in, beer and chinese cinnamons (Cinnamomum aromaticum). This could make cinnamic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Cinnamic acid. |
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CAS Number | 102-94-3 |
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Structure | |
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Synonyms | Synonym | Source |
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(2Z)-3-Phenyl-2-propenoic acid | ChEBI | (2Z)-3-Phenylacrylic acid | ChEBI | (Z)-3-Phenyl-2-propenoic acid | ChEBI | (Z)-Cinnamic acid | ChEBI | cis-beta-Carboxystyrene | ChEBI | cis-Zimtsaeure | ChEBI | (2Z)-3-Phenyl-2-propenoate | Generator | (2Z)-3-Phenylacrylate | Generator | (Z)-3-Phenyl-2-propenoate | Generator | (Z)-Cinnamate | Generator | cis-b-Carboxystyrene | Generator | cis-Β-carboxystyrene | Generator | Cinnamate | Generator | Cinnamic acid, 1-(13)C-labeled CPD | HMDB | Cinnamic acid, 13C-labeled CPD | HMDB | trans-Cinnamic acid | HMDB | (e)-Cinnamic acid, 2-(14)C-labeled CPD | HMDB | Cinnamic acid, (Z)-isomer | HMDB | Cinnamic acid, (trans)-(e)-isomer | HMDB | Cinnamic acid, 14C-labeled CPD | HMDB | Cinnamic acid, 3H-labeled CPD (Z)-isomer | HMDB | Cinnamic acid, sodium salt | HMDB | Cinnamic acid, sodium salt(Z)-isomer | HMDB | Sodium cinnamate | HMDB | e-Z Cinnamic acid | HMDB | Cinnamic acid, 2-(13)C-labeled CPD | HMDB | Cinnamic acid, 2-(14)C-labeled CPD | HMDB | Cinnamic acid, 3-(14)C-labeled CPD | HMDB | Cinnamic acid, radical ion(1-) | HMDB | e-Cinnamic acid | HMDB | Cinnamic acid, 1-14C-labeled CPD | HMDB | Cinnamic acid, 14C-labeled CPD (e)-isomer | HMDB | Cinnamic acid, 3H-labeled CPD (e)-isomer | HMDB | Cinnamic acid, ion(1-) | HMDB | Cinnamic acid, ion(1-)-(e)-isomer | HMDB | Cinnamic acid, nickel (+2) salt | HMDB | Cinnamic acid, potassium salt | HMDB | Cinnamic acid, sodium salt(e)-isomer | HMDB | Cinnamic acid, zinc salt(e)-isomer | HMDB | Tritium labeled (e)-cinnamic acid | HMDB | Tritium labeled (Z)-cinnamic acid | HMDB | (e)-3-Phenyl-2-propenoate | HMDB | (e)-3-Phenyl-2-propenoic acid | HMDB | 3-Phenyl-2-propenoate | HMDB | 3-Phenyl-2-propenoic acid | HMDB | 3-Phenyl-acrylate | HMDB | 3-Phenyl-acrylic acid | HMDB | 3-Phenylacrylate | HMDB | 3-Phenylacrylic acid | HMDB | 3-Phenylpropenoate | HMDB | 3-Phenylpropenoic acid | HMDB | Benzenepropenoate | HMDB | Benzenepropenoic acid | HMDB | Benzylideneacetic acid | HMDB | beta-Phenylacrylic acid | HMDB | Cinnamylic acid | HMDB | Phenylacrylate | HMDB | Phenylacrylic acid | HMDB | cis-Cinnamate | HMDB | (Z)-3-Phenylacrylic acid | HMDB | Allocinnamic acid | HMDB | Isocinnamic acid | HMDB | cis-Cinnamic acid | HMDB | Β-phenylacrylic acid | HMDB | Cinnamic acid | HMDB | (2Z)-3-Phenylprop-2-enoic acid | biospider | 2-Propenoic acid, 3-phenyl-, (Z)- | biospider | Cinnamic acid, (Z)- | biospider | cis-β-Carboxystyrene | biospider | Z-Cinnamic acid | biospider |
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Predicted Properties | |
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Chemical Formula | C9H8O2 |
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IUPAC name | (2Z)-3-phenylprop-2-enoic acid |
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InChI Identifier | 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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InChI Key | WBYWAXJHAXSJNI-SREVYHEPSA-N |
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Isomeric SMILES | OC(=O)\C=C/C1=CC=CC=C1 |
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Average Molecular Weight | 148.1586 |
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Monoisotopic Molecular Weight | 148.0524295 |
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Classification |
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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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Ontology |
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Ontology | No ontology term |
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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 72.96%; H 5.44%; O 21.60% | DFC |
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Melting Point | Mp 68° (trimorph.) | DFC |
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Boiling Point | Bp 95° (high vac.) | DFC |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | pKa 3.85 (25°) | DFC |
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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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Predicted GC-MS | Cinnamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0udi-1900000000-f00ddafc38ffb949fd1f | Spectrum | Predicted GC-MS | Cinnamic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0fl0-7930000000-f3ac0a061fb66ec84b5d | Spectrum | Predicted GC-MS | Cinnamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cinnamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cinnamic acid, TBDMS_1_1, 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, N/A (Annotated) | splash10-066s-4900000000-f4bfd33daf0938375a0d | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated) | splash10-0udi-0900000000-d93fb5a9c15682c1e6ee | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated) | splash10-004i-9000000000-9be1ef1ea4500691cb22 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-b4400af8b5aad0d8d323 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0fb9-9700000000-7d7dbe711d881767830e | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0900000000-20d69cc859de39f18004 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-1357b63887db6df1be7a | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0f89-0900000000-b8c6ecaf3fa85d1487a6 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-7900000000-0805b8dbbbd2777f28c4 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-6e7b31576f8ffd356252 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0f92-0900000000-c5fb484b178fce86b596 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0fb9-1900000000-36b618a3b50dc51ff302 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0900000000-5a19a7768eb87376d23c | 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-dd9a9ae0caad4bca05c8 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-530f30f323b6e6a53394 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0900000000-648b395c048d84ce7d9a | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fb9-9600000000-cb54ab97d7414eccc874 | 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, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, 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 | 5372954 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 35699 |
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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 | HCV54-E:HJX16-B |
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EAFUS ID | Not Available |
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Dr. Duke ID | CIS-CINNAMIC-ACID |
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BIGG ID | Not Available |
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KNApSAcK ID | C00034743 |
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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 | Cinnamic_acid |
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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 | — 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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