Record Information
Version1.0
Creation date2010-04-08 22:05:31 UTC
Update date2020-02-24 19:11:08 UTC
Primary IDFDB002766
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAcacetin
Description5,7-dihydroxy-2-(4-methoxyphenyl)-4h-chromen-4-one, also known as 4'-methoxy-5,7-dihydroxyflavone or acacetin, is a member of the class of compounds known as 4'-o-methylated flavonoids. 4'-o-methylated flavonoids are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone. Thus, 5,7-dihydroxy-2-(4-methoxyphenyl)-4h-chromen-4-one is considered to be a flavonoid lipid molecule. 5,7-dihydroxy-2-(4-methoxyphenyl)-4h-chromen-4-one is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 5,7-dihydroxy-2-(4-methoxyphenyl)-4h-chromen-4-one can be synthesized from apigenin. 5,7-dihydroxy-2-(4-methoxyphenyl)-4h-chromen-4-one is also a parent compound for other transformation products, including but not limited to, acacetin-7-O-beta-D-galactopyranoside, acacetin-8-C-neohesperidoside, and isoginkgetin. 5,7-dihydroxy-2-(4-methoxyphenyl)-4h-chromen-4-one can be found in ginkgo nuts, orange mint, and winter savory, which makes 5,7-dihydroxy-2-(4-methoxyphenyl)-4h-chromen-4-one a potential biomarker for the consumption of these food products.
CAS Number480-44-4
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.056 g/LALOGPS
logP3.46ALOGPS
logP2.85ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)6.58ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity77.4 m³·mol⁻¹ChemAxon
Polarizability28.9 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H12O5
IUPAC name5,7-dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one
InChI IdentifierInChI=1S/C16H12O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-8,17-18H,1H3
InChI KeyDANYIYRPLHHOCZ-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1
Average Molecular Weight284.2635
Monoisotopic Molecular Weight284.068473494
Classification
Description Belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent4'-O-methylated flavonoids
Alternative Parents
Substituents
  • 4p-methoxyflavonoid-skeleton
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSAcacetin, 1 TMS, GC-MS Spectrumsplash10-0a4r-7619000000-817802c448591650debaSpectrum
GC-MSAcacetin, 2 TMS, GC-MS Spectrumsplash10-03di-2733900000-3439dde28e0cc522d0d2Spectrum
Predicted GC-MSAcacetin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-08mi-5439700000-0c88005cfe5971080fe4Spectrum
Predicted GC-MSAcacetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05oc-0590000000-329b5fcd727ed303699bSpectrum
Predicted GC-MSAcacetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-000i-0190000000-f9171d6a3ce11fafc8dd2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0090020000-dfe55f293e647f3301402017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0uxr-0940000000-73352417553e57b4bee22017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0090000000-fbafd5ded7558cfda2302017-08-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-dc884c343b9a0499bc422016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-2d6e86a23b7201fe960c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v09-2490000000-2328f6d9ee073d28b5622016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-c1a5fd59543bc232e43d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-a047c9f433e7713707d92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zgi-3590000000-64205560724c680d55952016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-aaff95cd19cd93fcb8d82021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-139efeaa86e0903bbcb32021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01q9-0390000000-7b2e91829833aa7c385e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-a8b9e5ba8bfe303a94182021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-fc15b98c0acb8f4ba8e02021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0190000000-e42691aaeac33ae14a1c2021-09-24View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC01470
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI ID15335
Phenol-Explorer ID242
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCNN51-J:CNN51-J
EAFUS IDNot Available
Dr. Duke IDAPIGENIN-4'-METHYL-ETHER|ACACETIN
BIGG IDNot Available
KNApSAcK IDNot Available
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
Processing...
Biological Effects and Interactions
Health Effects / Bioactivities
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).