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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-09-11 01:32:46 UTC
NP-MRD IDNP0000005
Secondary Accession NumbersNone
Natural Product Identification
Common NameCoumarin
DescriptionCoumarin, 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.
Structure
Thumb
Synonyms
ValueSource
1,2-BenzopyroneChEBI
2-Propenoic acid, 3-(2-hydroxyphenyl)-, D-lactoneChEBI
2-Propenoic acid, 3-(2-hydroxyphenyl)-, delta-lactoneChEBI
2H-1-Benzopyran-2-oneChEBI
2H-Benzo[b]pyran-2-oneChEBI
5,6-Benzo-2-pyroneChEBI
Benzo-a-pyroneChEBI
Benzo-alpha-pyroneChEBI
cis-O-Coumarinic acid lactoneChEBI
CoumarineChEBI
Coumarinic anhydrideChEBI
CumarinChEBI
O-Hydroxycinnamic acid delta-lactoneChEBI
O-Hydroxycinnamic acid lactoneChEBI
RattexChEBI
Tonka bean camphorChEBI
Venalot monoKegg
2-Propenoate, 3-(2-hydroxyphenyl)-, D-lactoneGenerator
2-Propenoate, 3-(2-hydroxyphenyl)-, delta-lactoneGenerator
2-Propenoate, 3-(2-hydroxyphenyl)-, δ-lactoneGenerator
2-Propenoic acid, 3-(2-hydroxyphenyl)-, δ-lactoneGenerator
Benzo-α-pyroneGenerator
cis-O-Coumarinate lactoneGenerator
O-Hydroxycinnamate delta-lactoneGenerator
O-Hydroxycinnamate δ-lactoneGenerator
O-Hydroxycinnamic acid δ-lactoneGenerator
O-Hydroxycinnamate lactoneGenerator
1, 2-BenzopyroneHMDB
2-oxo-1,2-BenzopyranHMDB
2-oxo-2H-1-BenzopyranHMDB
2H-Chromen-2-oneHMDB
2H-Chromen-2-one (acd/name 4.0)HMDB
KumarinHMDB
O-Hydroxycinnamic lactoneHMDB
O-Hydroxyzimtsaure-lactonHMDB
{2h-benzo[b]pyran-2-one}HMDB
5,6-Benzo-alpha-pyroneHMDB
Chemical FormulaC9H6O2
Average Molecular Weight146.145
Monoisotopic Molecular Weight146.036779433
IUPAC Name2H-chromen-2-one
Traditional Namecoumarin
CAS Registry Number91-64-5
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 KeyZYGHJZDHTFUPRJ-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionView
1D NMR1H NMR SpectrumJSpectraViewer
1D NMR1H NMR SpectrumJSpectraViewer
1D NMR13C NMR SpectrumJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumJSpectraViewer
Species of Origin
SpeciesAnimalia; Plantae
Chemical Taxonomy
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).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassNot Available
Direct ParentCoumarins and derivatives
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point71 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.9 mg/mLNot Available
LogP2.23Not Available
Predicted Properties
PropertyValueSource
Water Solubility1 g/LALOGPS
logP1.72ALOGPS
logP1.78ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.55 m³·mol⁻¹ChemAxon
Polarizability14.36 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
User Submitted Data
Not Available
HMDB IDHMDB0001218
DrugBank IDDB04665
Phenol Explorer Compound ID635
FoodDB IDFDB030742
KNApSAcK IDC00002460
Chemspider ID13848793
KEGG Compound IDC05851
BioCyc IDCOUMARIN
BiGG ID46647
Wikipedia LinkCoumarin
METLIN ID3525
PubChem Compound323
PDB IDNot Available
ChEBI ID28794
References
General References
  1. Felter SP, Vassallo JD, Carlton BD, Daston GP: A safety assessment of coumarin taking into account species-specificity of toxicokinetics. Food Chem Toxicol. 2006 Apr;44(4):462-75. Epub 2005 Oct 3. [PubMed:16203076 ]