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Showing Compound coumarin (FDB030742)

Record Information
Version1.0
Creation date2015-05-07 19:59:13 UTC
Update date2025-11-19 03:01:59 UTC
Primary IDFDB030742
Secondary Accession Numbers
  • FDB011938
Chemical Information
FooDB Namecoumarin
DescriptionCoumarin, also known as 1,2-benzopyrone or benzo-alpha-pyrone, belongs to coumarins and derivatives class of compounds. Those are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Coumarin is slightly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Coumarin is a sweet, green, and new mown hay tasting compound and can be found in a number of food items such as malus (crab apple), sunburst squash (pattypan squash), european cranberry, and star anise, which makes coumarin a potential biomarker for the consumption of these food products. Coumarin can be found primarily in saliva. Coumarin is formally rated as an unfounded non-carcinogenic (IARC 3) potentially toxic compound. Coumarin was first synthesized in 1868. It is used in the pharmaceutical industry as a precursor reagent in the synthesis of a number of synthetic anticoagulant pharmaceuticals similar to dicoumarol, the notable ones being warfarin (brand name Coumadin) and some even more potent rodenticides that work by the same anticoagulant mechanism. 4-hydroxycoumarins are a type of vitamin K antagonist. Pharmaceutical (modified) coumarins were all developed from the study of sweet clover disease; see warfarin for this history. However, unmodified coumarin itself, as it occurs in plants, has no effect on the vitamin K coagulation system, or on the action of warfarin-type drugs .
CAS Number91-64-5
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
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
5,6-Benzo-alpha-pyroneMeSH
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
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
Chemical FormulaC9H6O2
IUPAC name2H-chromen-2-one
InChI IdentifierInChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
InChI KeyZYGHJZDHTFUPRJ-UHFFFAOYSA-N
Isomeric SMILESO=C1OC2=CC=CC=C2C=C1
Average Molecular Weight146.145
Monoisotopic Molecular Weight146.036779433
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00kb-9700000000-7a649c1e257a7ad17b9d2014-09-20View Spectrum
GC-MS2H-1-Benzopyran-2-one, non-derivatized, GC-MS Spectrumsplash10-014v-6900000000-3e901733dc003512f338Spectrum
GC-MS2H-1-Benzopyran-2-one, non-derivatized, GC-MS Spectrumsplash10-00kb-8900000000-89e86d11a0dc2841af42Spectrum
GC-MS2H-1-Benzopyran-2-one, non-derivatized, GC-MS Spectrumsplash10-014i-7900000000-25bab36f91f71ac65817Spectrum
GC-MS2H-1-Benzopyran-2-one, non-derivatized, GC-MS Spectrumsplash10-02tj-9600000000-4a54f8d648a87a9c5811Spectrum
GC-MS2H-1-Benzopyran-2-one, non-derivatized, GC-MS Spectrumsplash10-014v-6900000000-3e901733dc003512f338Spectrum
Predicted GC-MS2H-1-Benzopyran-2-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0gba-2900000000-12d24ebfbc2cbaa9d2e0Spectrum
Predicted GC-MS2H-1-Benzopyran-2-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0900000000-6ef9288c71771dd567742012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9100000000-93154d9b40c4d0fdd1ae2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-72ec22913d1d574be75b2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7L) , Positivesplash10-00kb-8900000000-89e86d11a0dc2841af422012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-014i-7900000000-25bab36f91f71ac658172012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-AX-505-H) , Positivesplash10-02tj-9600000000-6e4062e14fc72534c96a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-015a-0900000100-6ae81e23a1a6770a9f592017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-9200000000-38161abf759afe5aa9702017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-c06b97954c5a847401e82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-1900000000-6f05165347e6221503b02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0f6x-8900000000-6e9532ad6b20b76b3d4b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-9300000000-3f95abb339f5c1aea7902017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-9200000000-c404268b480236aaf1972017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0f6x-9500000000-da852779b618f093b7672017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9300000000-c29bd55b8ca9510aec2f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9100000000-161d49edf4310e8a785c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-3777f28f5438e1f091602017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-bfe432f57faff8d623182017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0089-0000800900-d301ec3931fa0374d57a2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-e5519a8faf9232fc0fcc2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-a6dc6c6c3032891bd1342015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-4900000000-139cc9674e0b2836e4412015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-e1154242f99d56bc5ed42015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-d6df7c01bbecf91182c92015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1900000000-961e88f9b351b2d27bec2015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
ChemSpider ID13848793
ChEMBL IDCHEMBL6466
KEGG Compound IDC05851
Pubchem Compound ID323
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB0001218
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00002460
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCoumarin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
green
  1. 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
  1. 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
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference