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Umbelliferone (FDB001094)

Record Information
Version1.0
Creation date2010-04-08 22:04:50 UTC
Update date2020-02-24 19:10:19 UTC
Primary IDFDB001094
Secondary Accession Numbers
  • FDB012649
Chemical Information
FooDB NameUmbelliferone
DescriptionUmbelliferone, also known as 7-hydroxycoumarin or hydrangin, belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. Umbelliferone is found, on average, in the highest concentration within anises (Pimpinella anisum) and beer. Umbelliferone has also been detected, but not quantified in, several different foods, such as ryes (Secale cereale), durians (Durio zibethinus), allspices (Pimenta dioica), japanese pumpkins (Cucurbita maxima), and garden onion (var.). This could make umbelliferone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Umbelliferone.
CAS Number93-35-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.38 g/LALOGPS
logP1.85ALOGPS
logP1.48ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)7.84ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.53 m³·mol⁻¹ChemAxon
Polarizability15.37 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H6O3
IUPAC name7-hydroxy-2H-chromen-2-one
InChI IdentifierInChI=1S/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H
InChI KeyORHBXUUXSCNDEV-UHFFFAOYSA-N
Isomeric SMILESOC1=CC2=C(C=C1)C=CC(=O)O2
Average Molecular Weight162.144
Monoisotopic Molecular Weight162.031694053
Classification
Description Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassHydroxycoumarins
Direct Parent7-hydroxycoumarins
Alternative Parents
Substituents
  • 7-hydroxycoumarin
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 66.67%; H 3.73%; O 29.60%DFC
Melting PointMp 230-232° (223-224°, 227-228°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKapKa1 7.7DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data[base] lmax 377 () (NaOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-03e9-6900000000-0be270410ca1ed2de5312015-03-01View Spectrum
GC-MSUmbelliferone, non-derivatized, GC-MS Spectrumsplash10-03gi-9700000000-61b0cf13acd34fc7ef62Spectrum
GC-MSUmbelliferone, non-derivatized, GC-MS Spectrumsplash10-03di-6900000000-dedc215fac13e97ee769Spectrum
GC-MSUmbelliferone, non-derivatized, GC-MS Spectrumsplash10-03gi-9700000000-61b0cf13acd34fc7ef62Spectrum
GC-MSUmbelliferone, non-derivatized, GC-MS Spectrumsplash10-03di-6900000000-dedc215fac13e97ee769Spectrum
Predicted GC-MSUmbelliferone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-02ai-0900000000-0624e9db800b4bf28fbbSpectrum
Predicted GC-MSUmbelliferone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-5940000000-389049e95813b961c56bSpectrum
Predicted GC-MSUmbelliferone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0kmi-0920000000-2cd49ad40f2f08fee3ab2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0kmi-0920000000-2cd49ad40f2f08fee3ab2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0kmi-0920000000-2cd49ad40f2f08fee3ab2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0kmi-0920000000-2cd49ad40f2f08fee3ab2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-03di-0900000000-1c416a1d92a90a4424ff2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-03e9-0900000000-ceab22ae6ab894db98ee2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0900000000-9f3b0c63320b7a16d26f2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-03di-0900000000-26b715dfa168a96a7f792017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-03di-0900000000-1349a86992b0b49b6c462017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-03di-0900000000-a4062ec204d8a8bbf5572017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-03e9-0900000000-1243c09e68f71ea9dbc92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-a0363e87c8dfdf5684e12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-ef5555622fcf5901817a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-01q9-0900000000-0a23407c9d3acb3a96462017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0089-3900000000-b06b1adaffe70bae68292017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0900000000-18c4c14a01ab29d764d22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0900000000-f9da00f6ddcb61b14a8c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-03e9-0900000000-ceab22ae6ab894db98ee2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-001i-0900000000-9f3b0c63320b7a16d26f2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-bafe152884074efd6ae42016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-ba2ab3999b706f4fba942016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-3900000000-94ba274c0fe68fcd55452016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-a37e719efb7afa07f7072016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-a5780fb402be64e17c802016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3900000000-f5ab2c793215524c01ec2016-08-03View Spectrum
NMR
TypeDescriptionView
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, 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
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
ChemSpider ID4444774
ChEMBL IDCHEMBL51628
KEGG Compound IDC09315
Pubchem Compound ID5281426
Pubchem Substance IDNot Available
ChEBI ID27510
Phenol-Explorer ID641
DrugBank IDNot Available
HMDB IDHMDB29865
CRC / DFC (Dictionary of Food Compounds) IDBSX04-T:BSX04-T
EAFUS IDNot Available
Dr. Duke IDUMBELLIFERONE
BIGG IDNot Available
KNApSAcK IDC00002503
HET ID07L
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
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
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
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti edemicDUKE
anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti mitoticDUKE
anti mutagenicDUKE
anti prostaglandin49020 A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti staphylococcic33282 A substance that kills or slows the growth of bacteria.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
candidicideDUKE
cholereticDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
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
photoactiveDUKE
sunscreen52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
xanthine oxidase inhibitor35634 An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— 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.