ChemFOnt: Showing chemical card for Quercetagetin (CFc000335563)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:28:11 UTC

Chemfont ID

CFc000335563

Molecule Identification

Common Name

Quercetagetin

Definition

2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one, also known as 6-hydroxyquercetin or 3,3',4',5,6,7-hexahydroxyflavone, is a member of the class of compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one is considered to be a flavonoid lipid molecule. 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one can be synthesized from quercetin. 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one is also a parent compound for other transformation products, including but not limited to, axillarin, eupatin, and patuletin. 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one is a bitter tasting compound found in sweet orange, which makes 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4-benzopyrone	ChEBI
3,3',4',5,6,7-Hexahydroxyflavone	ChEBI
6-Hydroxyquercetin	ChEBI
3,5,6,7,3',4'-Hexamethoxyflavone	MeSH
3,5,6,7-Tetrahydroxy-2-(3,4-dihydroxyphenyl)-4H-1-benzopyran-4-one	MeSH
Quercetogetin	MeSH

Chemical Formula

C₁₅H₁₀O₈

Average Molecular Weight

318.2351

Monoisotopic Molecular Weight

318.037567296

IUPAC Name

2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4H-chromen-4-one

Traditional Name

quercetagetin

CAS Registry Number

90-18-6

SMILES

OC1=CC2=C(C(O)=C1O)C(=O)C(O)=C(O2)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C15H10O8/c16-6-2-1-5(3-7(6)17)15-14(22)13(21)10-9(23-15)4-8(18)11(19)12(10)20/h1-4,16-20,22H

InChI Key

ZVOLCUVKHLEPEV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavonols

Alternative Parents

Substituents

3-hydroxyflavone
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
6-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Polyol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

flavonols (CHEBI:8695 )
hexahydroxyflavone (CHEBI:8695 )
flavonols (C10122 )
Flavones and Flavonols (C10122 )
Flavones and Flavonols (LMPK12112983 )

Functional Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Disposition

Source

Endogenous

Endogenous (FooDB: )

Plant

Plant (FooDB: )

Sweet orange (FooDB: FOOD00057)

Not Available

EC 1.1.1.21 (aldehyde reductase) inhibitor (FooDB: )
HIV-reverse-transcriptase inhibitor (FooDB: )

Anti bacterial (FooDB: )
Anti HIV (FooDB: )

Industrial application

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Antioxidant (FooDB: )
Antioxidant (FooDB: )

Coloring agent

Dye (FooDB: )

Agriculture

Pesticide (FooDB: )

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.32 g/L	ALOGPS
logP	1.7	ALOGPS
logP	1.85	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	6.56	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	147.68 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	78.84 m³·mol⁻¹	ChemAxon
Polarizability	29.49 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon