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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:47:22 UTC
Update Date2019-07-23 06:21:39 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 is an extremely weak basic (essentially neutral) compound (based on its pKa). 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. Outside of the human body, 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. This could make 3,4-dihydro-2H-1-benzopyran-2-one a potential biomarker for the consumption of these foods. 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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3 mg/mL at 37 °CNot Available
LogPNot AvailableNot Available
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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ffw-9500000000-19f4cacfc3593f445e42Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0910000000-3a0260eb973faa6f27dfSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-02du-2900000000-0780738b649dc11f75a4Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ffw-9500000000-19f4cacfc3593f445e42Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0910000000-3a0260eb973faa6f27dfSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-02du-2900000000-0780738b649dc11f75a4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fka-2900000000-071c9c2781c319fe04bfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-4aa1a496f0327462d05eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-bacf3cdab2c00f9d3a52Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-c86ad9f3b77d06e78084Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-1a2460bc4ea458349c97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-0900000000-9cfc6b98409c1ab92b17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-8900000000-4d6bcd5ccd07a0beeb52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-f2275d03bd7d08c74531Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6t-0900000000-bcc997cb9c43e840687cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6x-9600000000-5eebf3f0198d365245afSpectrum
MSMass Spectrum (Electron Ionization)splash10-006w-8900000000-1c291ea2d1c34d7a5a68Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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
FoodDB IDFDB015543
KNApSAcK IDNot Available
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
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.. .