Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2023-02-21 17:14:57 UTC |
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HMDB ID | HMDB0000567 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 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 can be obtained from oil of cinnamon, or from balsams such as storax. Cinnamic acid is a weakly acidic compound (based on its pKa). It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Cinnamic acid exists in all living organisms, ranging from bacteria to plants to humans. Outside of the human body, cinnamic acid has been detected, but not quantified in, chinese cinnamons. In plants, cinnamic acid is a central intermediate in the biosynthesis of myriad natural products include lignols (precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. |
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Structure | 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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Synonyms | Value | 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 |
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Chemical Formula | C9H8O2 |
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Average Molecular Weight | 148.1586 |
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Monoisotopic Molecular Weight | 148.0524295 |
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IUPAC Name | (2Z)-3-phenylprop-2-enoic acid |
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Traditional Name | cis-cinnamic acid |
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CAS Registry Number | 102-94-3 |
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SMILES | OC(=O)\C=C/C1=CC=CC=C1 |
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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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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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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 | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 132 - 135 °C | Not Available | Boiling Point | 265.00 to 266.00 °C. @ 760.00 mm Hg (est) | The Good Scents Company Information System | Water Solubility | 0.57 mg/mL at 25 °C | Not Available | LogP | 2.13 | HANSCH,C ET AL. (1995) |
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Experimental Chromatographic Properties | Experimental Collision Cross SectionsAdduct Type | Data Source | CCS Value (Å2) | Reference |
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[M+H]+ | Baker | 145.31 | 30932474 |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized | Show more...
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Cinnamic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0udi-1900000000-f00ddafc38ffb949fd1f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cinnamic acid GC-MS (1 TMS) - 70eV, Positive | splash10-0fl0-7930000000-f3ac0a061fb66ec84b5d | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cinnamic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cinnamic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cinnamic acid GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | 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 - Cinnamic acid Quattro_QQQ 10V, N/A-QTOF (Annotated) | splash10-066s-4900000000-f4bfd33daf0938375a0d | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cinnamic acid Quattro_QQQ 25V, N/A-QTOF (Annotated) | splash10-0udi-0900000000-d93fb5a9c15682c1e6ee | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cinnamic acid Quattro_QQQ 40V, N/A-QTOF (Annotated) | splash10-004i-9000000000-9be1ef1ea4500691cb22 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cinnamic acid 40V, Negative-QTOF | splash10-004i-9000000000-b4400af8b5aad0d8d323 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cinnamic acid 20V, Negative-QTOF | splash10-0fb9-9700000000-7d7dbe711d881767830e | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cinnamic acid 10V, Negative-QTOF | splash10-0udi-0900000000-20d69cc859de39f18004 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cinnamic acid 10V, Positive-QTOF | splash10-001i-0900000000-1357b63887db6df1be7a | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cinnamic acid 20V, Positive-QTOF | splash10-0f89-0900000000-b8c6ecaf3fa85d1487a6 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cinnamic acid 40V, Positive-QTOF | splash10-0udi-7900000000-0805b8dbbbd2777f28c4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cinnamic acid 10V, Negative-QTOF | splash10-0002-0900000000-6e7b31576f8ffd356252 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cinnamic acid 20V, Negative-QTOF | splash10-0f92-0900000000-c5fb484b178fce86b596 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cinnamic acid 40V, Negative-QTOF | splash10-0fb9-1900000000-36b618a3b50dc51ff302 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cinnamic acid 10V, Negative-QTOF | splash10-0udi-0900000000-5a19a7768eb87376d23c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cinnamic acid 20V, Negative-QTOF | splash10-0udi-0900000000-138b8c24fd394024a31a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cinnamic acid 40V, Negative-QTOF | splash10-004i-9200000000-dd9a9ae0caad4bca05c8 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cinnamic acid 10V, Positive-QTOF | splash10-001i-0900000000-530f30f323b6e6a53394 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cinnamic acid 20V, Positive-QTOF | splash10-0udi-0900000000-648b395c048d84ce7d9a | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cinnamic acid 40V, Positive-QTOF | splash10-0fb9-9600000000-cb54ab97d7414eccc874 | 2021-09-23 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | 2021-10-10 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, 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+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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Biological Properties |
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Cellular Locations | - Membrane (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 0.168 +/- 0.044 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 0.194 +/- 0.05 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 0.279 +/- 0.051 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 0.261 +/- 0.052 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 0.134 +/- 0.039 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 0.142 +/- 0.035 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 0.342 +/- 0.242 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 0.111 +/- 0.03 uM | Adult (>18 years old) | Male | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.77 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 1.6 (0.9-2.2) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.069 +/- 0.022 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB012698 |
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KNApSAcK ID | C00034743 |
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Chemspider ID | 10286933 |
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KEGG Compound ID | C10438 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Cinnamic acid |
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METLIN ID | 310 |
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PubChem Compound | 5372954 |
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PDB ID | Not Available |
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ChEBI ID | 35699 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1123131 |
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References |
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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) | Not Available |
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General 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 ]
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