Record Information |
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Version | 1.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2020-11-24 22:12:03 UTC |
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NP-MRD ID | NP0000005 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Coumarin |
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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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Structure | |
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Synonyms | Value | 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 | 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 | 5,6-Benzo-alpha-pyrone | HMDB |
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Chemical Formula | C9H6O2 |
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Average Molecular Weight | 146.145 |
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Monoisotopic Molecular Weight | 146.036779433 |
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IUPAC Name | 2H-chromen-2-one |
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Traditional Name | coumarin |
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CAS Registry Number | 91-64-5 |
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SMILES | O=C1OC2=CC=CC=C2C=C1 |
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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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Spectra |
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| | Species of Origin |
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Species | Animalia; Plantae |
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Chemical Taxonomy |
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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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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 71 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 1.9 mg/mL | Not Available | LogP | 2.23 | Not Available |
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Predicted Properties | |
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