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(R)-2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (FDB013434)

Record Information
Version1.0
Creation date2010-04-08 22:10:42 UTC
Update date2019-11-26 03:08:25 UTC
Primary IDFDB013434
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(R)-2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one
Description2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one belongs to the class of organic compounds known as benzoxazinones. These are organic compounds containing a benzene fused to an oxazine ring (a six-member aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group. 2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one has been detected, but not quantified in, several different foods, such as quinoas (Chenopodium quinoa), sorghums (Sorghum bicolor), flour, red rice (Oryza rufipogon), and wild rice (Zizania). This could make 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one.
CAS Number15893-52-4
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility24.6 g/LALOGPS
logP0.13ALOGPS
logP-0.055ChemAxon
logS-0.93ALOGPS
pKa (Strongest Acidic)7.85ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.47 m³·mol⁻¹ChemAxon
Polarizability19.29 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H9NO5
IUPAC name2,4-dihydroxy-7-methoxy-3,4-dihydro-2H-1,4-benzoxazin-3-one
InChI IdentifierInChI=1S/C9H9NO5/c1-14-5-2-3-6-7(4-5)15-9(12)8(11)10(6)13/h2-4,9,12-13H,1H3
InChI KeyGDNZNIJPBQATCZ-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC2=C(C=C1)N(O)C(=O)C(O)O2
Average Molecular Weight211.1715
Monoisotopic Molecular Weight211.048072403
Classification
Description Belongs to the class of organic compounds known as benzoxazinones. These are organic compounds containing a benzene fused to an oxazine ring (a six-member aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzoxazines
Sub ClassBenzoxazinones
Direct ParentBenzoxazinones
Alternative Parents
Substituents
  • Benzoxazinone
  • Benzomorpholine
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Oxazinane
  • Hemiacetal
  • Hydroxamic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Ether
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Foods

Grains:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 51.19%; H 4.30%; N 6.63%; O 37.88%DFC
Melting PointMp 168-169° (138°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
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
Predicted GC-MS(R)-2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-0900000000-53c2f5e27646045288afSpectrum
Predicted GC-MS(R)-2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-8940000000-d0f9b43343833c9e053bSpectrum
Predicted GC-MS(R)-2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(R)-2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0900000000-c15b25220502d9d185dd2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0190000000-81645df47c3fed0bd3a92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1290000000-4b18989a9733b9c9128d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pc0-8900000000-af10c52b30b91b0183432016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0190000000-ff36b9f2da9a370e6f452016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1960000000-ee23275c26b88778ad932016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200000000-180699a2eeca136cc1312016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0190000000-b79fb45b6c22516246bc2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-0950000000-3be199a9f3a68e9917c82021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-2900000000-10292325a80698ff13df2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ik9-0970000000-e9ff6d06efbb72e08f612021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-3900000000-6245e31fd6f132da0c392021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-6900000000-fdae439c7d67fc93bf972021-09-24View Spectrum
NMRNot Available
ChemSpider ID2268
ChEMBL IDNot Available
KEGG Compound IDC04720
Pubchem Compound ID2358
Pubchem Substance IDNot Available
ChEBI ID18048
Phenol-Explorer IDNot Available
DrugBank IDDB02185
HMDB IDHMDB34864
CRC / DFC (Dictionary of Food Compounds) IDKWX32-X:JBN49-H
EAFUS IDNot Available
Dr. Duke ID2-(2,4-DIHYDROXY-7-METHOXY-1,4(2H)-BENZOXAZIN-3(4H)
BIGG IDNot Available
KNApSAcK IDC00026498
HET IDNot Available
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 / BioactivitiesNot Available
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.