Record Information
Version1.0
Creation date2010-04-08 22:09:54 UTC
Update date2018-05-28 23:32:40 UTC
Primary IDFDB011938
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2H-1-Benzopyran-2-one
DescriptionOccurs in sweet clover. Banned by FDA for use in food Coumarin is a fragrant chemical compound in the benzopyrone chemical class, found in many plants, notably in high concentration in the tonka bean (Dipteryx odorata), vanilla grass (Anthoxanthum odoratum), sweet woodruff (Galium odoratum), mullein (Verbascum subspecies), sweet grass (Hierochloe odorata), cassia cinnamon (Cinnamomum aromaticum) and sweet clover (Fabaceae subspecies). It has a sweet odor, readily recognised as the scent of newly-mown hay, and has been used in perfumes since 1882. Sweet woodruff, sweet grass and sweet clover in particular are named for their sweet smell, which is due to their high content of this substance. When it occurs in high concentrations in forage plants, coumarin is a somewhat bitter-tasting appetite suppressant, and is presumed to be produced by plants as a defense chemical to discourage predation. Although coumarin itself has no anticoagulant properties, it is transformed into the natural anticoagulant dicoumarol by a number of species of fungi. Coumarin is used in the pharmaceutical industry as a precursor molecule in the synthesis of a number of synthetic anticoagulant pharmaceuticals similar to dicoumarol, the notable ones being warfarin (tradenamed "Coumadin," not to be confused with coumarin) and some even more potent rodenticides that work by the same anticoagulant mechanism. [Wikipedia].
CAS Number91-64-5
Structure
Thumb
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
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
{2H-benzo[b]pyran-2-one}HMDB
1-Benzopyran-2-onebiospider
2-Oxo-1,2-benzopyranbiospider
2-Oxo-2H-1-benzopyranbiospider
2H-Benzopyran-2-onebiospider
3-(2-Hydroxyphenyl)-2-propenoic delta-lactonebiospider
a-Benzopyronedb_source
Benzo-α-pyronebiospider
Benzo-2-pyronebiospider
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-Coumarinic acid lactonemanual
Coumarindb_source
Coumarinac lactonebiospider
Coumarinic acid lactonebiospider
Coumarinic lactonebiospider
o-Coumaric acid lactonebiospider
o-Hydroxycinnamic acid delta-lactonemanual
o-Hydroxycinnamic acid lactonemanual
o-Hydroxycinnamic lactonebiospider
Propenoic acid, 3-(2-hydroxyphenyl)-, delta-lactonebiospider
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014v-6900000000-3e901733dc003512f338View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kb-8900000000-89e86d11a0dc2841af42View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-7900000000-25bab36f91f71ac65817View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-02tj-9600000000-4a54f8d648a87a9c5811View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014v-6900000000-3e901733dc003512f338View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gba-2900000000-12d24ebfbc2cbaa9d2e0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0900000000-6ef9288c71771dd56774View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9100000000-93154d9b40c4d0fdd1aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-72ec22913d1d574be75bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7L) , Positivesplash10-00kb-8900000000-89e86d11a0dc2841af42View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-014i-7900000000-25bab36f91f71ac65817View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-AX-505-H) , Positivesplash10-02tj-9600000000-6e4062e14fc72534c96aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-015a-0900000100-6ae81e23a1a6770a9f59View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-9200000000-38161abf759afe5aa970View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-c06b97954c5a847401e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-1900000000-6f05165347e6221503b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0f6x-8900000000-6e9532ad6b20b76b3d4bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-9300000000-3f95abb339f5c1aea790View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-9200000000-c404268b480236aaf197View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0f6x-9500000000-da852779b618f093b767View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9300000000-c29bd55b8ca9510aec2fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9100000000-161d49edf4310e8a785cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-3777f28f5438e1f09160View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-bfe432f57faff8d62318View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0089-0000800900-d301ec3931fa0374d57aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-e5519a8faf9232fc0fccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-a6dc6c6c3032891bd134View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-4900000000-139cc9674e0b2836e441View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-e1154242f99d56bc5ed4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-d6df7c01bbecf91182c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1900000000-961e88f9b351b2d27becView in MoNA
MSMass Spectrum (Electron Ionization)splash10-00kb-9700000000-7a649c1e257a7ad17b9dView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
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.