| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:10:07 -0700 |
| HMDB ID |
HMDB01218 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
Coumarin |
| Description |
Coumarin is a chemical compound/poison found in many plants, notably in high concentration in the tonka bean, woodruff, and bison grass. It has a sweet scent, readily recognised as the scent of newly-mown hay. It has clinical value as the precursor for several anticoagulants, notably warfarin. --Wikipedia. Coumarins, as a class, are comprised of numerous naturally occurring benzo-alpha-pyrone compounds with important and diverse physiological activities. 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. Coumarin concentrations in these plants, spices, and foods range from <1 mg/kg in celery, 7000 mg/kg in cinnamon, and up to 87,000 mg/kg in cassia. An estimate of human exposure to coumarin from the diet has been calculated to be 0.02 mg/kg/day. Coumarin is used as an additive in perfumes and fragranced consumer products at concentrations ranging from <0.5% to 6.4% in fine fragrances to <0.01% in detergents. An estimate for systemic exposure of humans from the use of fragranced cosmetic products is 0.04 mg/kg BW/day, assuming complete dermal penetration. The use of coumarin as a food additive was banned by the FDA in 1954 based on reports of hepatotoxicity in rats. Due to its potential hepatotoxic effects in humans, the European Commission restricted coumarin from naturals as a direct food additive to 2 mg/kg food/day, with exceptions granting higher levels for alcoholic beverages, caramel, chewing gum, and certain 'traditional foods'. In addition to human exposure to coumarin from dietary sources and consumer products, coumarin is also used clinically as an antineoplastic and for the treatment of lymphedema and venous insufficiency. Exposure ranges from 11 mg/day for consumption of natural food ingredients to 7 g/day following clinical administration. Although adverse effects in humans following coumarin exposure are rare, and only associated with clinical doses, recent evidence indicates coumarin causes liver tumors in rats and mice and Clara cell toxicity and lung tumors in mice. The multiple effects as well as the ongoing human exposure to coumarin have resulted in a significant research effort focused on understanding the mechanism of coumarin induced toxicity/carcinogenicity and its human relevance. 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. In October 2004, the European Food Safety Authority (EFSA, 2004) reviewed coumarin to establish a tolerable daily intake (TDI) in foods. EFSA issued an opinion indicating that coumarin is not genotoxic, and that a threshold approach to safety assessment was most appropriate. EFSA recommended a TDI of 0 to 0.1 mg/kg BW/day. Including dietary contributions, the total human exposure is estimated to be 0.06 mg/kg/day. As a pharmaceutical, coumarin has been used in diverse applications with a wide variety of dosing regimens. Unlike coumadin and other coumarin derivatives, coumarin has no anti-coagulant activity. However, at low doses (typically 7 to 10 mg/day), coumarin has been used as a 'venotonic' to promote vein health and small venule blood flow. Additionally, coumarin has been used clinically in the treatment of high-protein lymphedema of various etiologies. (PMID: 16203076  ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- 1, 2-Benzopyrone
- 2-Oxo-1,2-benzopyran
- 2-Oxo-2H-1-Benzopyran
- 2H-1-Benzopyran-2-one
- 2H-Benzo[b]pyran-2-one
- 2H-Chromen-2-one
- 2H-Chromen-2-one (ACD/Name 4.0)
- 5,6-Benzo-2-pyrone
- Benzo-a-pyrone
- Benzo-alpha-pyrone
- cis-O-Coumarinic acid lactone
- Coumarin
- Coumarine
- Coumarinic anhydride
- Cumarin
- Kumarin
- O-Hydroxycinnamic acid lactone
- O-Hydroxycinnamic lactone
- O-Hydroxyzimtsaure-lacton
- Rattex
- Tonka bean camphor
- {2H-Benzo[b]pyran-2-one}
|
| Chemical Formula |
C9H6O2 |
| Average Molecular Weight |
146.1427 |
| Monoisotopic Molecular Weight |
146.036779436 |
| IUPAC Name |
2H-chromen-2-one |
| Traditional IUPAC Name |
2H-1-benzopyran-2-one |
| CAS Registry Number |
91-64-5 |
| SMILES |
O=C1OC2=CC=CC=C2C=C1 |
| InChI Identifier |
InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H |
| InChI Key |
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Aromatic Heteropolycyclic Compounds |
| Class |
Benzopyrans |
| Sub Class |
Coumarins and Derivatives |
| Other Descriptors |
- Benzopyrans
- Coumarins(KEGG)
- Phenylpropanoids(KEGG)
- a coumarin(Cyc)
- coumarins(ChEBI)
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| Substituents |
|
| Direct Parent |
Coumarins and Derivatives |
| Ontology |
|---|
| Status |
Expected and Not Quantified |
| Origin |
|
| Biofunction |
Not Available |
| Application |
Not Available |
| Cellular locations |
- Cytoplasm
- Extracellular
- Membrane (predicted from logP)
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| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| 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 |
|
| Spectra |
|---|
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| Biological Properties |
|---|
| Cellular Locations |
- Cytoplasm
- Extracellular
- Membrane (predicted from logP)
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| Biofluid Locations |
Not Available
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| Tissue Location |
Not Available
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| Pathways |
Not Available
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| Normal Concentrations |
|---|
|
Not Available |
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
DB04665 |
| Phenol Explorer Compound ID |
635 |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB011938 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
13848793 |
| KEGG Compound ID |
C05851 |
| BioCyc ID |
COUMARIN |
| BiGG ID |
46647 |
| Wikipedia Link |
Coumarin |
| NuGOwiki Link |
HMDB01218 |
| Metagene Link |
HMDB01218 |
| METLIN ID |
3525 |
| PubChem Compound |
323 |
| PDB ID |
COU |
| ChEBI ID |
28794 |
| References |
|---|
| Synthesis Reference |
Huang, Zhong-jing. Synthesis of coumarin under microwave irradiation. Guangxi Huagong (2001), 30(3), 1-2. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
Not Available
|
