Record Information
Version1.0
Creation date2010-04-08 22:09:54 UTC
Update date2020-09-17 15:38:51 UTC
Primary IDFDB011938
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2H-1-Benzopyran-2-one
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.
CAS Number91-64-5
Structure
Thumb
Synonyms
SynonymSource
{2H-benzo[b]pyran-2-one}HMDB
1-Benzopyran-2-onebiospider
1, 2-BenzopyroneHMDB
1,2-Benzopyronemanual
2-Oxo-1,2-benzopyranbiospider
2-Oxo-2H-1-benzopyranbiospider
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)-, D-lactoneChEBI
2-Propenoic acid, 3-(2-hydroxyphenyl)-, delta-lactonebiospider
2-Propenoic acid, 3-(2-hydroxyphenyl)-, δ-lactoneGenerator
2H-Benzo[b]pyran-2-onebiospider
2H-Benzopyran-2-onebiospider
2H-Chromen-2-onebiospider
2H-Chromen-2-one (acd/name 4.0)HMDB
3-(2-Hydroxyphenyl)-2-propenoic delta-lactonebiospider
5,6-Benzo-2-pyronebiospider
5,6-Benzo-alpha-pyronebiospider
a-Benzopyronedb_source
Benzo-α-pyronebiospider
Benzo-2-pyronebiospider
Benzo-a-pyronemanual
Benzo-alpha-pyronebiospider
Benzo-α-pyroneGenerator
Benzopyran-2-onebiospider
Chromen-2-onebiospider
Cinnamic acid, o-hydroxy-, «delta»-lactonebiospider
Cinnamic acid, o-hydroxy-, delta-lactonebiospider
cis-o-Coumaric acid lactonebiospider
cis-O-Coumarinate lactoneGenerator
cis-o-Coumarinic acid lactonemanual
Coumarindb_source
Coumarinac lactonebiospider
CoumarineChEBI
Coumarinic acid lactonebiospider
Coumarinic anhydridedb_source
Coumarinic lactonebiospider
Cumarindb_source
KumarinHMDB
o-Coumaric acid lactonebiospider
O-Hydroxycinnamate delta-lactoneGenerator
O-Hydroxycinnamate lactoneGenerator
O-Hydroxycinnamate δ-lactoneGenerator
o-Hydroxycinnamic acid delta-lactonemanual
o-Hydroxycinnamic acid lactonemanual
O-Hydroxycinnamic acid δ-lactoneGenerator
o-Hydroxycinnamic lactonebiospider
O-Hydroxyzimtsaure-lactonHMDB
Propenoic acid, 3-(2-hydroxyphenyl)-, delta-lactonebiospider
Rattexmanual
Tonka bean camphormanual
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
ClassificationNot classified
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 73.97%; H 4.14%; O 21.90%DFC
Melting PointMp 70°DFC
Boiling PointBp 291°DFC
Experimental Water Solubility1.9 mg/mL at 20 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP2.23HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data307 (e 5623) (MeOH) (Berdy)DFC
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 ID28794
Phenol-Explorer ID635
DrugBank IDDB04665
HMDB IDHMDB01218
CRC / DFC (Dictionary of Food Compounds) IDHBX68-O:HBX68-O
EAFUS ID768
Dr. Duke IDCOUMARIN|COUMARINS
BIGG ID46647
KNApSAcK IDNot Available
HET IDCOU
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID91-64-5
GoodScent IDrw1003831
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 / Bioactivities
DescriptorIDDefinitionReference
aldose reductase inhibitor48550 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
allelochemicDUKE
analgesic35480 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
anestheticDUKE
anti aggregantDUKE
anti androgenic35497 A compound which inhibits or antagonises the biosynthesis or actions of androgens.DUKE
anti brucellosic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti diuretic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti edemicDUKE
anti esherichicDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti lymphedemicDUKE
anti melanomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti metastatic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti mitoticDUKE
anti mononuccleoticDUKE
anti mutagenicDUKE
anti mycoplasmoticDUKE
anti psittacoticDUKE
anti psoriac52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti toxoplasmotic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
bacteristat33282 A substance that kills or slows the growth of bacteria.DUKE
bruchiphobeDUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
carcinogenic50903 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
cardiodepressant38070 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
cardiotonic38070 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
chemopreventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
diabetic-macular-edema inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
emeticDUKE
estrogenicDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hemorrhagic50248 Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.DUKE
hepatotoxic50908 A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.DUKE
hypnoticDUKE
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
immunostimulant50847 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
juvabionalDUKE
larvistatDUKE
lymphocytogenicDUKE
lymphokineticDUKE
narcotic35482 A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.DUKE
ovicideDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
phagocytoticDUKE
piscicideDUKE
respirodepressantDUKE
rodenticide33288 A substance used to destroy rodent pests.DUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
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
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
tonka
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
new mown hay
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
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.