Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:28 UTC |
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Update date | 2019-11-26 02:57:47 UTC |
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Primary ID | FDB002667 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | trans-p-Methoxycinnamic acid |
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Description | 4-Methoxycinnamic 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. 4-Methoxycinnamic acid is found, on average, in the highest concentration within turmerics (Curcuma longa). 4-Methoxycinnamic acid has also been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), milk (cow), and wild celeries (Apium graveolens). This could make 4-methoxycinnamic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Methoxycinnamic acid. |
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CAS Number | 830-09-1 |
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Structure | |
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Synonyms | Synonym | Source |
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4-Methoxycinnamate | Generator | 3-(4-Methoxyphenyl)acrylic acid | ChEMBL, HMDB | Para-methoxycinnamic acid | ChEMBL, HMDB | 3-(4-Methoxyphenyl)acrylate | Generator, HMDB | Para-methoxycinnamate | Generator, HMDB | (e)-3-(4-Methoxyphenyl)acrylate | HMDB | (e)-3-(4-Methoxyphenyl)acrylic acid | HMDB | 3-(4-Methoxy-phenyl)-acrylate | HMDB | 3-(4-Methoxy-phenyl)-acrylic acid | HMDB | 3-(4-Methoxyphenyl)-2-propenoate | HMDB | 3-(4-Methoxyphenyl)-2-propenoic acid | HMDB | 4-Methoxy cinnamate | HMDB | 4-Methoxy cinnamic acid | HMDB | O-Methyl-P-coumarate | HMDB | O-Methyl-P-coumaric acid | HMDB | P-Hydroxy methyl cinnamate | HMDB | P-Methoxy ciannamate | HMDB | P-Methoxy ciannamic acid | HMDB | P-Methoxycinnamate | HMDB | P-Methoxycinnamic acid | HMDB | trans-4-Methoxycinnamate | HMDB | trans-4-Methoxycinnamic acid | HMDB | 4-Methoxycinnamate, aluminum salt | MeSH, HMDB | 4-Methoxycinnamate, (e)-isomer | MeSH, HMDB | 4-Methoxycinnamate, (Z)-isomer | MeSH, HMDB | 4-Methoxycinnamate, zinc salt | MeSH, HMDB | 4-Methoxycinnamate, zirconium salt | MeSH, HMDB | e-P-Methoxycinnamic acid | MeSH, HMDB | 4-Methoxycinnamate, calcium salt | MeSH, HMDB | 4-Methoxycinnamate, magnesium salt | MeSH, HMDB | 4-Methoxycinnamate, potassium salt | MeSH, HMDB | 4-Methoxycinnamate, sodium salt | MeSH, HMDB | (2E)-3-(4-Methoxyphenyl)prop-2-enoate | Generator, HMDB | 4-Methoxycinnamic acid | MeSH | (2E)-3-(4-Methoxyphenyl)-2-propenoic acid | HMDB | (E)-3-(4-Methoxyphenyl)-2-propenoic acid | HMDB | (E)-3-(4-Methoxyphenyl)acrylic acid | HMDB | (E)-4-Methoxycinnamic acid | HMDB | (E)-p-Methoxycinnamic acid | HMDB | 3-(4-Methoxyphenyl)propenoic acid | HMDB | 4'-Methoxycinnamic acid | HMDB | 4-Methyoxycinnamic acid | HMDB | 4’-Methoxycinnamic acid | HMDB | O-Methyl-p-coumaric acid | HMDB | p-Methoxycinnamic acid | HMDB | trans-3-(4-Methoxyphenyl)-2-propenoic acid | HMDB | trans-p-Methoxycinnamic acid | HMDB | trans-p-Methoxycinnamate | Generator, HMDB | (2E)-3-(4-methoxyphenyl)prop-2-enoic acid | biospider | (E)-3-(4-Methoxy-phenyl)-acrylic acid | biospider | (E)-3-(4-Methoxyphenyl)acrylate | biospider | 3-(4-Methoxyphenyl)-2-propenoic acid, 9CI | db_source | 3-(4-methoxyphenyl)acrylic acid | biospider | 3-(4-methoxyphenyl)prop-2-enoic acid | biospider | O-Methyl-p-coumarate | biospider | p-Hydroxy methyl cinnamate | biospider | p-Methoxycinnamate | biospider | para-Methoxycinnamate | biospider | para-Methoxycinnamic acid | biospider | trans-2-Propenoic acid, 3-(4-methoxyphenyl)- | biospider | trans-3-(4-Methoxyphenyl)acrylic acid | biospider |
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Predicted Properties | |
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Chemical Formula | C10H10O3 |
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IUPAC name | (2E)-3-(4-methoxyphenyl)prop-2-enoic acid |
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InChI Identifier | InChI=1S/C10H10O3/c1-13-9-5-2-8(3-6-9)4-7-10(11)12/h2-7H,1H3,(H,11,12)/b7-4+ |
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InChI Key | AFDXODALSZRGIH-QPJJXVBHSA-N |
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Isomeric SMILES | COC1=CC=C(\C=C\C(O)=O)C=C1 |
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Average Molecular Weight | 178.1846 |
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Monoisotopic Molecular Weight | 178.062994186 |
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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
- Phenoxy compound
- Anisole
- Methoxybenzene
- Styrene
- Phenol ether
- Alkyl aryl ether
- Monocyclic benzene moiety
- Benzenoid
- Carboxylic acid derivative
- Carboxylic acid
- Ether
- Monocarboxylic acid or derivatives
- Organic oxygen compound
- Carbonyl group
- Organic oxide
- Organooxygen compound
- Hydrocarbon derivative
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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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 | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 67.41%; H 5.66%; O 26.94% | DFC |
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Melting Point | Mp 188-189.5° (174°) | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 1.97 mg/mL at 25 oC | STEPHEN,H & STEPHEN,T (1963) |
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Experimental logP | 2.68 | HANSCH,C ET AL. (1995) |
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Experimental pKa | pKa 4.54 (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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GC-MS | trans-p-Methoxycinnamic acid, 1 TMS, GC-MS Spectrum | splash10-03du-2920000000-dece72c3ca5c90bfc547 | Spectrum | GC-MS | trans-p-Methoxycinnamic acid, non-derivatized, GC-MS Spectrum | splash10-004i-0900000000-a59af9ca91b1d5bd7182 | Spectrum | GC-MS | trans-p-Methoxycinnamic acid, non-derivatized, GC-MS Spectrum | splash10-004i-7900000000-6075ede461ba4ee4c7cd | Spectrum | GC-MS | trans-p-Methoxycinnamic acid, non-derivatized, GC-MS Spectrum | splash10-004i-1900000000-e899894a8c3562db43a5 | Spectrum | GC-MS | trans-p-Methoxycinnamic acid, non-derivatized, GC-MS Spectrum | splash10-03du-2920000000-dece72c3ca5c90bfc547 | Spectrum | Predicted GC-MS | trans-p-Methoxycinnamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-03gi-1900000000-cc8f6e9174dff780d643 | Spectrum | Predicted GC-MS | trans-p-Methoxycinnamic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0080-9650000000-bb37ec4824ae491674e5 | Spectrum | Predicted GC-MS | trans-p-Methoxycinnamic acid, non-derivatized, 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) | splash10-03di-0900000000-12552bc1ab86525703a0 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00pi-5900000000-9632d41fa295f06b5381 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-004u-9100000000-a6dac09530cfcfc28868 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive | splash10-004i-0900000000-a59af9ca91b1d5bd7182 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive | splash10-004i-7900000000-8e025153eeb590c13daa | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0fb9-0900000000-c6baccb046bfcd7d6282 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative | splash10-014i-1900000000-3927439c287110a6a2f1 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-03e9-1900000000-03cba42101a868fcbdbb | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-03e9-1900000000-53a3d7a661e7d42fabbf | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-00mo-9600000000-b0e876994fe40230d56f | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-00lr-1900000000-32372664024a7a1cba27 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0fb9-0900000000-c6baccb046bfcd7d6282 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-014i-1900000000-3927439c287110a6a2f1 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-03e9-1900000000-03cba42101a868fcbdbb | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-03e9-1900000000-53a3d7a661e7d42fabbf | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-00mo-9600000000-1dd0b8897a3d399d48fc | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-00lr-1900000000-32372664024a7a1cba27 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-03di-0900000000-2c4cab05840440c8ef92 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-03di-0900000000-3954121d114e7a125401 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0900000000-f0f239b49fe3cc116d97 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03e9-0900000000-d7031d18cf315b765cbf | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-9800000000-881ce76bbf7add1a8162 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0900000000-0d57f82612687cf62c68 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-057i-0900000000-c2111775e672e2666fbd | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-02u3-1900000000-295574bc9205dd1a7c79 | 2017-09-01 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 609479 |
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ChEMBL ID | CHEMBL95770 |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 699414 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 48541 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB02040 |
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CRC / DFC (Dictionary of Food Compounds) ID | CMP73-U:CMZ41-H |
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EAFUS ID | Not Available |
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Dr. Duke ID | P-METHOXY-CINNAMIC-ACID |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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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 | Not Available |
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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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anti pyretic | 35493 | A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever. | DUKE | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | hemolytic | | | DUKE | hypoglycemic | 35526 | A drug which lowers the blood glucose level. | 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 |
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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 | 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 | — 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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