Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:09:58 UTC |
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Update date | 2019-11-26 03:06:04 UTC |
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Primary ID | FDB012052 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Cinnamic acid |
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Description | trans-Cinnamic acid, also known as (e)-cinnamic acid or phenylacrylic acid, 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. trans-Cinnamic acid exists in all living species, ranging from bacteria to plants to humans. trans-Cinnamic acid is a sweet, balsam, and cinnamon tasting compound. trans-Cinnamic acid is found, on average, in the highest concentration within a few different foods, such as chinese cinnamons (Cinnamomum aromaticum), olives (Olea europaea), and lingonberries (Vaccinium vitis-idaea) and in a lower concentration in corianders (Coriandrum sativum), american cranberries (Vaccinium macrocarpon), and red raspberries (Rubus idaeus). trans-Cinnamic acid has also been detected, but not quantified in, several different foods, such as black tea, broccolis (Brassica oleracea var. italica), red bell peppers (Capsicum annuum), sweet bays (Laurus nobilis), and teas (Camellia sinensis). This could make trans-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 trans-Cinnamic acid. |
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CAS Number | 621-82-9 |
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Structure | |
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Synonyms | Synonym | Source |
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(2E)-3-Phenyl-2-propenoic acid | ChEBI | (2E)-3-Phenylacrylic acid | ChEBI | (e)-3-Phenyl-2-propenoic acid | ChEBI | (e)-Cinnamate | ChEBI | (e)-Cinnamic acid | ChEBI | Benzeneacrylic acid | ChEBI | PHENYLETHYLENECARBOXYLIC ACID | ChEBI | trans-3-Phenylacrylic acid | ChEBI | trans-beta-Carboxystyrene | ChEBI | trans-Cinnamate | ChEBI | trans-Zimtsaeure | ChEBI | (2E)-3-Phenyl-2-propenoate | Generator | (2E)-3-Phenylacrylate | Generator | (e)-3-Phenyl-2-propenoate | Generator | Benzeneacrylate | Generator | PHENYLETHYLENECARBOXYLate | Generator | trans-3-Phenylacrylate | Generator | trans-b-Carboxystyrene | Generator | trans-Β-carboxystyrene | Generator | (2E)-2-Phenyl-2-propenoate | HMDB | (2E)-2-Phenyl-2-propenoic acid | HMDB | (e)-3-Phenylacrylate | HMDB | (e)-3-Phenylacrylic acid | HMDB | (e)-3-Phenylprop-2-enoate | HMDB | (e)-3-Phenylprop-2-enoic acid | HMDB | trans-3-Phenyl-2-propenoate | HMDB | trans-3-Phenyl-2-propenoic acid | HMDB | Cinnamic acid, 14C-labeled CPD | HMDB | Cinnamic acid, 2-(14)C-labeled CPD | HMDB | Cinnamic acid, 3-(14)C-labeled CPD | HMDB | Cinnamic acid, (Z)-isomer | HMDB | Cinnamic acid, 2-(13)C-labeled CPD | HMDB | Cinnamic acid, 3H-labeled CPD (e)-isomer | HMDB | Cinnamic acid, 3H-labeled CPD (Z)-isomer | HMDB | Cinnamic acid, ion(1-)-(e)-isomer | HMDB | Cinnamic acid, sodium salt | HMDB | Cinnamic acid, sodium salt(e)-isomer | HMDB | Cinnamic acid, sodium salt(Z)-isomer | HMDB | Cinnamic acid, (trans)-(e)-isomer | HMDB | Cinnamic acid, 14C-labeled CPD (e)-isomer | HMDB | Cinnamic acid, ion(1-) | HMDB | Cinnamic acid, nickel (+2) salt | HMDB | Cinnamic acid, potassium salt | HMDB | Cinnamic acid, zinc salt(e)-isomer | HMDB | Cinnamic acid, 13C-labeled CPD | HMDB | Cinnamic acid | HMDB | (2E)-3-Phenylprop-2-enoic acid | HMDB | (2E)-Cinnamic acid | HMDB | 3-Phenyl-(e)-2-propenoic acid | HMDB | 3-Phenyl-2-propenoic acid | HMDB | 3-Phenylacrylic acid | HMDB | Phenylacrylic acid | HMDB | beta-Phenylacrylic acid | HMDB | Β-phenylacrylic acid | HMDB | trans-Cinnamic acid | HMDB | (2Z)-3-Phenyl-2-propenoate | Generator | (2Z)-3-Phenylacrylate | Generator | (Z)-3-Phenyl-2-propenoate | Generator | (Z)-Cinnamate | Generator | β-Phenylacrylic acid | biospider | 2-Propenoic acid, 3-phenyl- | biospider | 3-Phenyl-2-propenoate | biospider | 3-Phenyl-acrylate | biospider | 3-Phenyl-acrylic acid | biospider | 3-Phenylacrylate | biospider | 3-Phenylprop-2-enoic acid | biospider | 3-Phenylpropenoate | biospider | 3-Phenylpropenoic acid | biospider | b-Phenylacrylic acid | biospider | Benzenepropenoate | biospider | Benzenepropenoic acid | biospider | Benzylideneacetic acid | biospider | Cinnamate | biospider | Cinnamic acid, 8CI | db_source | Cinnamylic acid | biospider | cis-b-Carboxystyrene | Generator | cis-Cinnamate | Generator | cis-Zimtsaeure | ChEBI | cis-β-carboxystyrene | Generator | FEMA 2288 | db_source | Phenylacrylate | biospider | Phenylethylenecarboxylic acid | biospider |
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Predicted Properties | |
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Chemical Formula | C9H8O2 |
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IUPAC name | (2E)-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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Disposition | Route of exposure: Source: Biological location: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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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 | 132-135 oC | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 0.57 mg/mL at 25 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Experimental logP | 2.13 | HANSCH,C ET AL. (1995) |
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Experimental pKa | 4.44 | |
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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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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0f6t-6900000000-77686ecc684f3b46bea6 | 2014-09-20 | View Spectrum | GC-MS | trans-Cinnamic acid, 1 TMS, GC-MS Spectrum | splash10-0ue9-0910000000-4a7bcdfadd383bf577dc | Spectrum | GC-MS | trans-Cinnamic acid, 1 TMS, GC-MS Spectrum | splash10-0fb9-6920000000-727a2eb761e6e52fb47d | Spectrum | GC-MS | trans-Cinnamic acid, 1 TMS, GC-MS Spectrum | splash10-117i-2920000000-f0d9ccc40786362ae4ad | Spectrum | GC-MS | trans-Cinnamic acid, non-derivatized, GC-MS Spectrum | splash10-0ue9-0910000000-4a7bcdfadd383bf577dc | Spectrum | GC-MS | trans-Cinnamic acid, non-derivatized, GC-MS Spectrum | splash10-0fb9-6920000000-727a2eb761e6e52fb47d | Spectrum | GC-MS | trans-Cinnamic acid, non-derivatized, GC-MS Spectrum | splash10-117i-2920000000-f0d9ccc40786362ae4ad | Spectrum | Predicted GC-MS | trans-Cinnamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0ue9-2900000000-b105b3fcb63636d0d16f | Spectrum | Predicted GC-MS | trans-Cinnamic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0fl0-7930000000-f3ac0a061fb66ec84b5d | Spectrum | Predicted GC-MS | trans-Cinnamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | trans-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, Positive (Annotated) | splash10-001i-0900000000-3107a2a1bec368528f82 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0ufr-6900000000-b0299d34fa9bb16b8258 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0udi-0900000000-4a879de8ea4f3acb0ae2 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-0002-0900000000-88ad8c9c837a057bb2a5 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-0udi-0900000000-18280fe18e43043d9e21 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0fb9-9600000000-04d36ba7639bc85e2023 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-004i-9000000000-a8417274c4493c5b5871 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-004i-9100000000-d3712417826a69667981 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0002-0900000000-37c486fa03918355413c | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0f6t-0900000000-218a5babf0ab7c31c498 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0002-0900000000-88ad8c9c837a057bb2a5 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0udi-0900000000-e3a4fcaa911f14d3790d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0fb9-9600000000-04d36ba7639bc85e2023 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9000000000-a8417274c4493c5b5871 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9100000000-d3712417826a69667981 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0f6t-0900000000-218a5babf0ab7c31c498 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0udi-0900000000-f095c04fe81b2890cb1a | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0udi-0900000000-1bb9599f57d5b1c1688b | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0002-0900000000-37c486fa03918355413c | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000t-0900000000-f5b771d960092fa83d2c | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0uea-0900000000-58b4769b89ab3883fb05 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-6900000000-9f4710d90f0cafac6d7b | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-d015607beb5136324414 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0f6t-0900000000-ff32add65ca52cbaae83 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0fb9-3900000000-f2450299b70c3ec0faec | 2016-09-12 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (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 | 10286933 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C10438 |
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Pubchem Compound ID | 5372954 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 27386 |
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Phenol-Explorer ID | 549 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB00567 |
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CRC / DFC (Dictionary of Food Compounds) ID | HCV54-E:HCV54-E |
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EAFUS ID | 644 |
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Dr. Duke ID | CINNAMIC-ACID |
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BIGG ID | Not Available |
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KNApSAcK ID | C00029961 |
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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 | rw1350711 |
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SuperScent ID | 444539 |
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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 | Descriptor | ID | Definition | Reference |
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aldose reductase inhibitor | 48550 | An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21). | DUKE | allergenic | 50904 | A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy. | DUKE | anesthetic | | | DUKE | anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | anti mutagenic | | | DUKE | anti spasmodic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | choleretic | | | DUKE | dermatitigenic | | | DUKE | flavor | 48318 | A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. | DUKE | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | herbicide | 24527 | A substance used to destroy plant pests. | DUKE | laxative | 50503 | An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic. | DUKE | lipoxygenase inhibitor | 35856 | A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes. | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | tyrosinase inhibitor | 59997 | Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals. | DUKE | vermifuge | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE |
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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 | Flavor | Citations |
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cinnamon |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| honey |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| balsam |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| sweet |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| storax |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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Files |
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MSDS | show |
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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 | — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070. — 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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