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Showing Compound Acacetin (FDB002766)

Record Information
Version1.0
Creation date2010-04-08 22:05:31 UTC
Update date2025-11-18 22:40:29 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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
4'-Methoxy-5,7-dihydroxyflavoneChEBI
5,7-Dihydroxy-2-(4-methoxyphenyl)-4-benzopyroneChEBI
AcacetinChEBI
LinarigeninChEBI
5,7-Dihydroxy-4'-methoxyflavoneKegg
5,7-Dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one, 9CIdb_source
Apigenin 4'-methyl etherdb_source
Buddleoflavonoldb_source
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
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 67.60%; H 4.25%; O 28.14%DFC
Melting PointNot Available
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
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 ID4444099
ChEMBL IDCHEMBL243664
KEGG Compound IDC01470
Pubchem Compound ID5280442
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 IDAcacetin
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 agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.DUKE
Allergenic50904 A substance that triggers an immune response, causing allergic reactions. Its biological role is to stimulate the immune system, but it has no therapeutic applications. Key medical uses include diagnosing allergies and developing immunotherapies to desensitize patients to specific allergens, reducing the risk of severe reactions.DUKE
Anti aflatoxin35222 An agent that neutralizes or removes aflatoxins, toxic compounds produced by mold, reducing the risk of liver damage and cancer. Therapeutically, it is used to prevent aflatoxin poisoning, commonly in food safety and liver protection applications, and may have potential in cancer prevention and treatment.DUKE
Anti-allergic50857 An agent that reduces or blocks allergic reactions, commonly used to manage symptoms of allergies, such as itching, sneezing, and inflammation, by inhibiting the release of histamine and other chemical mediators, providing relief in conditions like hay fever, asthma, and skin allergies.DUKE
Anti histaminic37956 An agent that blocks histamine receptors, reducing allergic symptoms. Therapeutically, it alleviates itching, sneezing, and runny nose, commonly used in managing allergies, itching, and hives, as well as treating conditions like anaphylaxis and allergic rhinitis.DUKE
Anti-malarial33281 An agent that prevents or treats malaria, a disease caused by Plasmodium parasites. It works by targeting the parasite's life cycle, reducing symptoms and preventing transmission. Therapeutically, anti-malarials are used to treat and prevent malaria, as well as to manage related conditions such as babesiosis and toxoplasmosis.DUKE
Anti-mutagenicAn agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.DUKE
Aromatase inhibitor50790 An agent that blocks the activity of aromatase, an enzyme converting androgens to estrogens, reducing estrogen levels. Therapeutically, it's used to treat hormone-sensitive breast cancer, endometriosis, and infertility, by decreasing estrogen-dependent growth and symptoms.DUKE
Hepatoprotective62868 An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.DUKE
Iodothyronine-deiodinase inhibitor23924 An agent that blocks the activity of iodothyronine-deiodinase, regulating thyroid hormone levels. It is used therapeutically to manage thyroid disorders, particularly in cases of hyperthyroidism, and has potential applications in treating thyroid-related conditions, such as Graves' disease and thyroid cancer.DUKE
MutagenicAn agent that induces genetic mutations, altering DNA sequences. It plays a biological role in evolution and adaptation. Therapeutically, mutagenic agents are used in cancer treatment, such as chemotherapy, and in gene therapy to introduce beneficial traits. Key medical uses include oncology and genetic research.DUKE
PlasmodicideAn agent that kills malaria parasites, playing a crucial role in treating and preventing malaria. Therapeutically, it targets Plasmodium species, and its key medical uses include prophylaxis and treatment of malaria, particularly in endemic areas, helping to reduce transmission and alleviate disease burden.DUKE
ProtisticideAn agent that kills protozoans, used as a herbicide or in therapeutic applications to treat protozoan infections, with key medical uses including managing parasitic diseases and infections.DUKE
Topoisomerase-I inhibitor50276 An agent that blocks the activity of topoisomerase I, an enzyme involved in DNA replication. It is used therapeutically in cancer treatment, particularly for solid tumors, by inducing DNA damage and inhibiting cancer cell growth, with key medical uses in colorectal, lung, and breast cancers.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).