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Showing Compound 3,4-Dihydro-2H-1-benzopyran-2-one (FDB015543)

Record Information
Version1.0
Creation date2010-04-08 22:11:54 UTC
Update date2019-11-26 03:11:48 UTC
Primary IDFDB015543
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3,4-Dihydro-2H-1-benzopyran-2-one
Description3,4-Dihydro-2H-1-benzopyran-2-one, also known as dihydrocoumarin or 1,2-benzodihydropyrone, belongs to the class of organic compounds known as 3,4-dihydrocoumarins. These are 3,4-dihydrogenated coumarins. Coumarin is a bicyclic compound that are 1-benzopyran carrying an oxo group at the 2-position. 3,4-Dihydro-2H-1-benzopyran-2-one exists in all living organisms, ranging from bacteria to humans. 3,4-Dihydro-2H-1-benzopyran-2-one is a sweet, almond, and cinnamon tasting compound. 3,4-Dihydro-2H-1-benzopyran-2-one has been detected, but not quantified in, several different foods, such as green vegetables, pulses, sour cherries (Prunus cerasus), and tarragons (Artemisia dracunculus). This could make 3,4-dihydro-2H-1-benzopyran-2-one a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on 3,4-Dihydro-2H-1-benzopyran-2-one.
CAS Number119-84-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1,2-BenzodihydropyroneChEBI
2-Hydroxydihydrocinnamic acid lactoneChEBI
3,4-Dihydro-2H-chromen-2-oneChEBI
BenzodihydropyroneChEBI
DihydrocoumarinChEBI
HydrocoumarinChEBI
Melilotic acid lactoneChEBI
Melilotic lactoneChEBI
MelilotinChEBI
MelilotolChEBI
O-Hydroxydihydrocinnamic acid lactoneChEBI
O-Hydroxyhydrocinnamic acid delta-lactoneChEBI
3,4-DihydrocoumarinKegg
2-Hydroxydihydrocinnamate lactoneGenerator
Melilotate lactoneGenerator
O-Hydroxydihydrocinnamate lactoneGenerator
O-Hydroxyhydrocinnamate delta-lactoneGenerator
O-Hydroxyhydrocinnamate δ-lactoneGenerator
O-Hydroxyhydrocinnamic acid δ-lactoneGenerator
2-Hydroxyhydrocinnamic lactoneHMDB
3,4-dihydro-1-Benzopyran-2-oneHMDB
3,4-dihydro-CoumarinHMDB
3,4-DihydroxycoumarinHMDB
dihydro-BenzopyranoneHMDB
FEMA 2381HMDB
Hydrocinnamic acid, O-hydroxy-, delta-lactoneHMDB
Hydrocoumarin, 8ciHMDB
Melilotin (coumarin)HMDB
Melilotin??HMDB
O-Hydroxyhydrocinnamic acid lactoneHMDB
2-Chromanonedb_source
2-Oxochromandb_source
2H-1-Benzopyran-2-one, 3,4-dihydro-biospider
3,4-Dihydro-1-benzopyran-2-onebiospider
Benzopyranone, dihydro-biospider
Chroman-2-onebiospider
Chroman, 2-oxo-biospider
Coumarin, 3,4-dihydro-biospider
Hydrocinnamic acid, o-hydroxy-, delta-lactonebiospider
Hydrocoumarin, 8CIdb_source
o-Hydroxydihydrocinnamic acid lactonebiospider
o-Hydroxyhydrocinnamic acid delta-lactonebiospider
o-Hydroxyhydrocinnamic acid lactonebiospider
Predicted Properties
PropertyValueSource
Water Solubility2.25 g/LALOGPS
logP1.66ALOGPS
logP1.89ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity40.46 m³·mol⁻¹ChemAxon
Polarizability15.09 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H8O2
IUPAC name3,4-dihydro-2H-1-benzopyran-2-one
InChI IdentifierInChI=1S/C9H8O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-4H,5-6H2
InChI KeyVMUXSMXIQBNMGZ-UHFFFAOYSA-N
Isomeric SMILESO=C1CCC2=CC=CC=C2O1
Average Molecular Weight148.1586
Monoisotopic Molecular Weight148.0524295
Classification
Description Belongs to the class of organic compounds known as 3,4-dihydrocoumarins. These are 3,4-dihydrogenated coumarins. Coumarin is a bicyclic compound that are 1-benzopyran carrying an oxo group at the 2-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
Class3,4-dihydrocoumarins
Sub ClassNot Available
Direct Parent3,4-dihydrocoumarins
Alternative Parents
Substituents
  • 3,4-dihydrocoumarin
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Benzenoid
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Carbonyl group
  • 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:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 72.96%; H 5.44%; O 21.60%DFC
Melting PointMp 25°DFC
Boiling PointBp13 145°DFC
Experimental Water Solubility3 mg/mL at 37 oCBEILSTEIN
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)splash10-006w-8900000000-1c291ea2d1c34d7a5a682015-03-01View Spectrum
GC-MS3,4-Dihydro-2H-1-benzopyran-2-one, non-derivatized, GC-MS Spectrumsplash10-0ffw-9500000000-19f4cacfc3593f445e42Spectrum
GC-MS3,4-Dihydro-2H-1-benzopyran-2-one, non-derivatized, GC-MS Spectrumsplash10-0002-0910000000-3a0260eb973faa6f27dfSpectrum
GC-MS3,4-Dihydro-2H-1-benzopyran-2-one, non-derivatized, GC-MS Spectrumsplash10-02du-2900000000-0780738b649dc11f75a4Spectrum
GC-MS3,4-Dihydro-2H-1-benzopyran-2-one, non-derivatized, GC-MS Spectrumsplash10-0ffw-9500000000-19f4cacfc3593f445e42Spectrum
GC-MS3,4-Dihydro-2H-1-benzopyran-2-one, non-derivatized, GC-MS Spectrumsplash10-0002-0910000000-3a0260eb973faa6f27dfSpectrum
GC-MS3,4-Dihydro-2H-1-benzopyran-2-one, non-derivatized, GC-MS Spectrumsplash10-02du-2900000000-0780738b649dc11f75a4Spectrum
Predicted GC-MS3,4-Dihydro-2H-1-benzopyran-2-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fka-2900000000-071c9c2781c319fe04bfSpectrum
Predicted GC-MS3,4-Dihydro-2H-1-benzopyran-2-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3,4-Dihydro-2H-1-benzopyran-2-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-4aa1a496f0327462d05e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-bacf3cdab2c00f9d3a522017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-c86ad9f3b77d06e780842017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-1a9803adbe959ab8c3972021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-0900000000-c86ad9f3b77d06e780842021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-4aa1a496f0327462d05e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-014i-0900000000-e00f4063d413008ffe402021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-bacf3cdab2c00f9d3a522021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-1a2460bc4ea458349c972015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-0900000000-9cfc6b98409c1ab92b172015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-8900000000-4d6bcd5ccd07a0beeb522015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-f2275d03bd7d08c745312015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6t-0900000000-bcc997cb9c43e840687c2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6x-9600000000-5eebf3f0198d365245af2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-c273ad6f431d1239485b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0592-1900000000-c7524399be04f94a7e322021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-9400000000-364ed3e27ac756fed7b12021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-a4c75ebd26f0ac23a7eb2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-1900000000-107b906f2798b39151902021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00vl-6900000000-6809bdcaa3f757b499af2021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
ChemSpider ID640
ChEMBL IDCHEMBL89306
KEGG Compound IDC02274
Pubchem Compound ID660
Pubchem Substance IDNot Available
ChEBI ID16151
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36626
CRC / DFC (Dictionary of Food Compounds) IDKDD18-Y:KDD18-Y
EAFUS ID913
Dr. Duke IDDIHYDROCOUMARIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1001531
SuperScent ID660
Wikipedia IDNot Available
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
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
creamy
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
coconut
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
almond
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
tobacco
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
sweet
  1. 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.
coumarin
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cinnamon
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
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).