Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:09:54 UTC |
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Update date | 2020-09-17 15:38:51 UTC |
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Primary ID | FDB011938 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 2H-1-Benzopyran-2-one |
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Description | Coumarin, also known as 1,2-benzopyrone or rattex, belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). These investigations have revealed significant species differences in coumarin metabolism and toxicity such that the mechanism of coumarin induced effects in rodents, and the relevance of these findings for the safety assessment of coumarin exposure in humans are now better understood. The parent compound, coumarin, occurs naturally in many plants, natural spices, and foods such as tonka bean, cassia (bastard cinnamon or Chinese cinnamon), cinnamon, melilot (sweet clover), green tea, peppermint, celery, bilberry, lavender, honey (derived both from sweet clover and lavender), and carrots, as well as in beer, tobacco, wine, and other foodstuffs. EFSA recommended a TDI of 0 to 0.1 mg/kg BW/day. Coumarin is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, coumarin is involved in nicotine action pathway. Coumarin is a sweet, bitter, and green tasting compound. Outside of the human body, Coumarin has been detected, but not quantified in, several different foods, such as jicama, gooseberries, parsley, colorado pinyons, and tree ferns. This could make coumarin a potential biomarker for the consumption of these foods. Coumarin is a potentially toxic compound. |
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CAS Number | 91-64-5 |
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Structure | |
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Synonyms | Synonym | Source |
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1,2-Benzopyrone | ChEBI | 2-Propenoic acid, 3-(2-hydroxyphenyl)-, D-lactone | ChEBI | 2-Propenoic acid, 3-(2-hydroxyphenyl)-, delta-lactone | ChEBI | 2H-1-Benzopyran-2-one | ChEBI | 2H-Benzo[b]pyran-2-one | ChEBI | 5,6-Benzo-2-pyrone | ChEBI | Benzo-a-pyrone | ChEBI | Benzo-alpha-pyrone | ChEBI | cis-O-Coumarinic acid lactone | ChEBI | Coumarine | ChEBI | Coumarinic anhydride | ChEBI | Cumarin | ChEBI | O-Hydroxycinnamic acid delta-lactone | ChEBI | O-Hydroxycinnamic acid lactone | ChEBI | Rattex | ChEBI | Tonka bean camphor | ChEBI | Venalot mono | Kegg | 2-Propenoate, 3-(2-hydroxyphenyl)-, D-lactone | Generator | 2-Propenoate, 3-(2-hydroxyphenyl)-, delta-lactone | Generator | 2-Propenoate, 3-(2-hydroxyphenyl)-, δ-lactone | Generator | 2-Propenoic acid, 3-(2-hydroxyphenyl)-, δ-lactone | Generator | Benzo-α-pyrone | Generator | cis-O-Coumarinate lactone | Generator | O-Hydroxycinnamate delta-lactone | Generator | O-Hydroxycinnamate δ-lactone | Generator | O-Hydroxycinnamic acid δ-lactone | Generator | O-Hydroxycinnamate lactone | Generator | 5,6-Benzo-alpha-pyrone | MeSH | 1, 2-Benzopyrone | HMDB | 2-oxo-1,2-Benzopyran | HMDB | 2-oxo-2H-1-Benzopyran | HMDB | 2H-Chromen-2-one | HMDB | 2H-Chromen-2-one (acd/name 4.0) | HMDB | Kumarin | HMDB | O-Hydroxycinnamic lactone | HMDB | O-Hydroxyzimtsaure-lacton | HMDB | {2h-benzo[b]pyran-2-one} | HMDB | {2H-benzo[b]pyran-2-one} | HMDB | 1-Benzopyran-2-one | biospider | 2-Oxo-1,2-benzopyran | biospider | 2-Oxo-2H-1-benzopyran | biospider | 2H-Benzopyran-2-one | biospider | 3-(2-Hydroxyphenyl)-2-propenoic delta-lactone | biospider | a-Benzopyrone | db_source | Benzo-α-pyrone | biospider | Benzo-2-pyrone | biospider | Benzopyran-2-one | biospider | Chromen-2-one | biospider | Cinnamic acid, o-hydroxy-, «delta»-lactone | biospider | Cinnamic acid, o-hydroxy-, delta-lactone | biospider | cis-o-Coumaric acid lactone | biospider | cis-o-Coumarinic acid lactone | manual | Coumarin | db_source | Coumarinac lactone | biospider | Coumarinic acid lactone | biospider | Coumarinic lactone | biospider | o-Coumaric acid lactone | biospider | o-Hydroxycinnamic acid delta-lactone | manual | o-Hydroxycinnamic acid lactone | manual | o-Hydroxycinnamic lactone | biospider | Propenoic acid, 3-(2-hydroxyphenyl)-, delta-lactone | biospider |
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Predicted Properties | |
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Chemical Formula | C9H6O2 |
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IUPAC name | 2H-chromen-2-one |
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InChI Identifier | InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H |
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InChI Key | ZYGHJZDHTFUPRJ-UHFFFAOYSA-N |
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Isomeric SMILES | O=C1OC2=CC=CC=C2C=C1 |
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Average Molecular Weight | 146.145 |
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Monoisotopic Molecular Weight | 146.036779433 |
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Classification |
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Description | Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Coumarins and derivatives |
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Sub Class | Not Available |
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Direct Parent | Coumarins and derivatives |
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Alternative Parents | |
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Substituents | - Coumarin
- 1-benzopyran
- Benzopyran
- Pyranone
- Benzenoid
- Pyran
- Heteroaromatic compound
- Lactone
- Oxacycle
- Organoheterocyclic compound
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic 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 | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 73.97%; H 4.14%; O 21.90% | DFC |
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Melting Point | Mp 70° | DFC |
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Boiling Point | Bp 291° | DFC |
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Experimental Water Solubility | 1.9 mg/mL at 20 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Experimental logP | 2.23 | HANSCH,C ET AL. (1995) |
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Experimental pKa | Not Available | |
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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 | 307 (e 5623) (MeOH) (Berdy) | DFC |
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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) | splash10-00kb-9700000000-7a649c1e257a7ad17b9d | 2014-09-20 | View Spectrum | GC-MS | 2H-1-Benzopyran-2-one, non-derivatized, GC-MS Spectrum | splash10-014v-6900000000-3e901733dc003512f338 | Spectrum | GC-MS | 2H-1-Benzopyran-2-one, non-derivatized, GC-MS Spectrum | splash10-00kb-8900000000-89e86d11a0dc2841af42 | Spectrum | GC-MS | 2H-1-Benzopyran-2-one, non-derivatized, GC-MS Spectrum | splash10-014i-7900000000-25bab36f91f71ac65817 | Spectrum | GC-MS | 2H-1-Benzopyran-2-one, non-derivatized, GC-MS Spectrum | splash10-02tj-9600000000-4a54f8d648a87a9c5811 | Spectrum | GC-MS | 2H-1-Benzopyran-2-one, non-derivatized, GC-MS Spectrum | splash10-014v-6900000000-3e901733dc003512f338 | Spectrum | Predicted GC-MS | 2H-1-Benzopyran-2-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0gba-2900000000-12d24ebfbc2cbaa9d2e0 | Spectrum | Predicted GC-MS | 2H-1-Benzopyran-2-one, 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) | splash10-0002-0900000000-6ef9288c71771dd56774 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0006-9100000000-93154d9b40c4d0fdd1ae | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-014i-9000000000-72ec22913d1d574be75b | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-7L) , Positive | splash10-00kb-8900000000-89e86d11a0dc2841af42 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive | splash10-014i-7900000000-25bab36f91f71ac65817 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (JEOL JMS-AX-505-H) , Positive | splash10-02tj-9600000000-6e4062e14fc72534c96a | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - DI-ESI-qTof , Positive | splash10-015a-0900000100-6ae81e23a1a6770a9f59 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-000i-9200000000-38161abf759afe5aa970 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0002-0900000000-c06b97954c5a847401e8 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0002-1900000000-6f05165347e6221503b0 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0f6x-8900000000-6e9532ad6b20b76b3d4b | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0006-9300000000-3f95abb339f5c1aea790 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0006-9200000000-c404268b480236aaf197 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0f6x-9500000000-da852779b618f093b767 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0006-9300000000-c29bd55b8ca9510aec2f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0006-9100000000-161d49edf4310e8a785c | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0002-0900000000-3777f28f5438e1f09160 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0udi-0900000000-bfe432f57faff8d62318 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0089-0000800900-d301ec3931fa0374d57a | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0900000000-e5519a8faf9232fc0fcc | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-0900000000-a6dc6c6c3032891bd134 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-4900000000-139cc9674e0b2836e441 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-e1154242f99d56bc5ed4 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0900000000-d6df7c01bbecf91182c9 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0udi-1900000000-961e88f9b351b2d27bec | 2015-05-27 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 13848793 |
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ChEMBL ID | CHEMBL6466 |
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KEGG Compound ID | C05851 |
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Pubchem Compound ID | 323 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 28794 |
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Phenol-Explorer ID | 635 |
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DrugBank ID | DB04665 |
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HMDB ID | HMDB01218 |
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CRC / DFC (Dictionary of Food Compounds) ID | HBX68-O:HBX68-O |
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EAFUS ID | 768 |
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Dr. Duke ID | COUMARIN|COUMARINS |
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BIGG ID | 46647 |
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KNApSAcK ID | Not Available |
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HET ID | COU |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | 91-64-5 |
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GoodScent ID | rw1003831 |
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SuperScent ID | Not Available |
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Wikipedia ID | Coumarin |
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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 | allelochemic | | | DUKE | analgesic | 35480 | An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms. | DUKE | anesthetic | | | DUKE | anti aggregant | | | DUKE | anti androgenic | 35497 | A compound which inhibits or antagonises the biosynthesis or actions of androgens. | DUKE | anti brucellosic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | anti cancer | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | anti diuretic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti edemic | | | DUKE | anti esherichic | | | DUKE | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | anti lymphedemic | | | DUKE | anti melanomic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | anti metastatic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | anti mitotic | | | DUKE | anti mononuccleotic | | | DUKE | anti mutagenic | | | DUKE | anti mycoplasmotic | | | DUKE | anti psittacotic | | | DUKE | anti psoriac | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti toxoplasmotic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | antitumor | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | bacteristat | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | bruchiphobe | | | DUKE | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | carcinogenic | 50903 | A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities. | DUKE | cardiodepressant | 38070 | A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. | DUKE | cardiotonic | 38070 | A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. | DUKE | chemopreventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | diabetic-macular-edema inhibitor | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | emetic | | | DUKE | estrogenic | | | DUKE | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | hemorrhagic | 50248 | Drug that acts on blood and blood-forming organs and those that affect the hemostatic system. | DUKE | hepatotoxic | 50908 | A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals. | DUKE | hypnotic | | | DUKE | hypoglycemic | 35526 | A drug which lowers the blood glucose level. | DUKE | immunostimulant | 50847 | A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity. | DUKE | juvabional | | | DUKE | larvistat | | | DUKE | lymphocytogenic | | | DUKE | lymphokinetic | | | DUKE | narcotic | 35482 | A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood. | DUKE | ovicide | | | 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 | phagocytotic | | | DUKE | piscicide | | | DUKE | respirodepressant | | | DUKE | rodenticide | 33288 | A substance used to destroy rodent pests. | DUKE | sedative | 35717 | A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. | 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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green |
- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
| sweet |
- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| tonka |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| new mown hay |
- 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 | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — 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.
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