Back to Compounds

Showing Compound 2-(4-Hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one (FDB021139)

Record Information
Version1.0
Creation date2010-04-08 22:15:30 UTC
Update date2019-11-26 03:19:56 UTC
Primary IDFDB021139
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-(4-Hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one
Description2-(4-Hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton. 2-(4-Hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one has been detected, but not quantified in, citrus and mandarin orange (clementine, tangerine). This could make 2-(4-hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-(4-Hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one.
CAS Number157072-30-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.0053 g/LALOGPS
logP4.36ALOGPS
logP3.27ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)8.55ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area74.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity106.53 m³·mol⁻¹ChemAxon
Polarizability40.28 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC22H20O6
IUPAC name2-(4-hydroxyphenyl)-3,5-dimethoxy-8,8-dimethyl-4H,8H-pyrano[2,3-h]chromen-4-one
InChI IdentifierInChI=1S/C22H20O6/c1-22(2)10-9-14-15(28-22)11-16(25-3)17-18(24)21(26-4)19(27-20(14)17)12-5-7-13(23)8-6-12/h5-11,23H,1-4H3
InChI KeyVNNMTQJSNKAONW-UHFFFAOYSA-N
Isomeric SMILESCOC1=C2C(=O)C(OC)=C(OC2=C2C=CC(C)(C)OC2=C1)C1=CC=C(O)C=C1
Average Molecular Weight380.3906
Monoisotopic Molecular Weight380.125988372
Classification
Description Belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassPyranoflavonoids
Direct ParentPyranoflavonoids
Alternative Parents
Substituents
  • Pyranoflavonoid
  • 3-methoxyflavonoid-skeleton
  • 5-methoxyflavonoid-skeleton
  • 4'-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Monohydroxyflavonoid
  • Pyranochromene
  • 3-methoxychromone
  • 2,2-dimethyl-1-benzopyran
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Pyranone
  • Benzenoid
  • Monocyclic benzene moiety
  • Pyran
  • Vinylogous ester
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2-(4-Hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0gb9-0239000000-74faec2e2cdf71e96980Spectrum
Predicted GC-MS2-(4-Hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00ri-3293800000-cc19d14e68afd9864679Spectrum
Predicted GC-MS2-(4-Hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-1c67c241259738d907302017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-1009000000-09f18069bf6db02bc4562017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016s-9625000000-1119c8000a2273a852182017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-02ede051f8ea664868252017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0009000000-cd4df4c9690e76a45f1b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000m-2933000000-122fa7269653b51d85b42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-f62f9fb5e728cdb885e72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0029000000-8eb9f8fafd49b1a2c6d52021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-017l-4493000000-903792b3e4919ae49f552021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-f13f27e51c8cc55afced2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0009000000-37a7d33633d9f15e946a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1094000000-81c8a561ecf0f0f57a112021-09-22View Spectrum
NMRNot Available
ChemSpider ID30777543
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB41236
CRC / DFC (Dictionary of Food Compounds) IDKRG99-G:NMJ67-I
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00005079
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
Mandarin orange (Clementine, Tangerine)Expected but not quantifiedNot AvailableKNAPSACK
Showing 1 to 1 of 1 entries
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— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.