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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:47:22 UTC
Update Date2022-03-07 02:55:00 UTC
HMDB IDHMDB0036626
Secondary Accession Numbers
  • HMDB36626
Metabolite Identification
Common Name3,4-Dihydro-2H-1-benzopyran-2-one
Description3,4-Dihydro-2H-1-benzopyran-2-one, also known as 3,4-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, and tarragons. A chromanone that is the 3,4-dihydro derivative of coumarin.
Structure
Data?1563862899
Synonyms
ValueSource
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
Chemical FormulaC9H8O2
Average Molecular Weight148.1586
Monoisotopic Molecular Weight148.0524295
IUPAC Name3,4-dihydro-2H-1-benzopyran-2-one
Traditional Namedihydrocoumarin
CAS Registry Number119-84-6
SMILES
O=C1CCC2=CC=CC=C2O1
InChI Identifier
InChI=1S/C9H8O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-4H,5-6H2
InChI KeyVMUXSMXIQBNMGZ-UHFFFAOYSA-N
Chemical Taxonomy
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

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point25 °CNot Available
Boiling Point271.00 to 272.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility3 mg/mL at 37 °CNot Available
LogP2.428 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.56731661259
DarkChem[M-H]-128.21831661259
DeepCCS[M+H]+129.82830932474
DeepCCS[M-H]-126.56530932474
DeepCCS[M-2H]-163.74630932474
DeepCCS[M+Na]+138.70930932474
AllCCS[M+H]+130.432859911
AllCCS[M+H-H2O]+125.632859911
AllCCS[M+NH4]+134.832859911
AllCCS[M+Na]+136.132859911
AllCCS[M-H]-129.632859911
AllCCS[M+Na-2H]-130.332859911
AllCCS[M+HCOO]-131.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4-Dihydro-2H-1-benzopyran-2-oneO=C1CCC2=CC=CC=C2O12488.3Standard polar33892256
3,4-Dihydro-2H-1-benzopyran-2-oneO=C1CCC2=CC=CC=C2O11309.5Standard non polar33892256
3,4-Dihydro-2H-1-benzopyran-2-oneO=C1CCC2=CC=CC=C2O11383.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one EI-B (Non-derivatized)splash10-0ffw-9500000000-19f4cacfc3593f445e422017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one GC-EI-TOF (Non-derivatized)splash10-0002-0910000000-3a0260eb973faa6f27df2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one GC-EI-TOF (Non-derivatized)splash10-02du-2900000000-0780738b649dc11f75a42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one EI-B (Non-derivatized)splash10-0ffw-9500000000-19f4cacfc3593f445e422018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one GC-EI-TOF (Non-derivatized)splash10-0002-0910000000-3a0260eb973faa6f27df2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one GC-EI-TOF (Non-derivatized)splash10-02du-2900000000-0780738b649dc11f75a42018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fka-2900000000-071c9c2781c319fe04bf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-006w-8900000000-1c291ea2d1c34d7a5a682015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one LC-ESI-QTOF , positive-QTOFsplash10-0002-0900000000-4aa1a496f0327462d05e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one LC-ESI-QTOF , positive-QTOFsplash10-0a4i-0900000000-bacf3cdab2c00f9d3a522017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one LC-ESI-QTOF , positive-QTOFsplash10-0a4i-0900000000-c86ad9f3b77d06e780842017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 20V, Positive-QTOFsplash10-0a4i-0900000000-1a9803adbe959ab8c3972021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 30V, Positive-QTOFsplash10-0a4i-0900000000-c86ad9f3b77d06e780842021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 10V, Positive-QTOFsplash10-0002-0900000000-4aa1a496f0327462d05e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 35V, Negative-QTOFsplash10-014i-0900000000-e00f4063d413008ffe402021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 20V, Positive-QTOFsplash10-0a4i-0900000000-bacf3cdab2c00f9d3a522021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 10V, Positive-QTOFsplash10-0002-0900000000-1a2460bc4ea458349c972015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 20V, Positive-QTOFsplash10-0a4j-0900000000-9cfc6b98409c1ab92b172015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 40V, Positive-QTOFsplash10-0pb9-8900000000-4d6bcd5ccd07a0beeb522015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 10V, Negative-QTOFsplash10-0002-0900000000-f2275d03bd7d08c745312015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 20V, Negative-QTOFsplash10-0f6t-0900000000-bcc997cb9c43e840687c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 40V, Negative-QTOFsplash10-0f6x-9600000000-5eebf3f0198d365245af2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 10V, Positive-QTOFsplash10-0002-0900000000-c273ad6f431d1239485b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 20V, Positive-QTOFsplash10-0592-1900000000-c7524399be04f94a7e322021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 40V, Positive-QTOFsplash10-0fb9-9400000000-364ed3e27ac756fed7b12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 10V, Negative-QTOFsplash10-0002-0900000000-a4c75ebd26f0ac23a7eb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 20V, Negative-QTOFsplash10-014j-1900000000-107b906f2798b39151902021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydro-2H-1-benzopyran-2-one 40V, Negative-QTOFsplash10-00vl-6900000000-6809bdcaa3f757b499af2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015543
KNApSAcK IDC00054085
Chemspider ID640
KEGG Compound IDC02274
BioCyc IDDIHYDROCOUMARIN
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound660
PDB IDNot Available
ChEBI ID16151
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1001531
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .