ChemFOnt: Showing chemical card for Quercetin 3-O-methyl-ether (CFc000334350)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:15:23 UTC

Chemfont ID

CFc000334350

Molecule Identification

Common Name

Quercetin 3-O-methyl-ether

Definition

Quercetin 3-methyl ether, also known as 3',4',5,7-tetrahydroxy-3-methoxyflavone or isorhamnetin, is a member of the class of compounds known as 3-o-methylated flavonoids. 3-o-methylated flavonoids are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone. Thus, quercetin 3-methyl ether is considered to be a flavonoid lipid molecule. Quercetin 3-methyl ether is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Quercetin 3-methyl ether can be synthesized from quercetin. Quercetin 3-methyl ether can also be synthesized into 3-O-methylquercetin 7-O-beta-glucopyranosyl-4'-O-beta-D-glucopyranoside. Quercetin 3-methyl ether can be found in common bean, which makes quercetin 3-methyl ether a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-methoxy-4H-1-benzopyran-4-one	ChEBI
3-Methoxy-5,7,3',4'-tetrahydroxyflavone	ChEBI
3-O-Methylquercetin	ChEBI
3',4',5,7-Tetrahydroxy-3-methoxyflavone	Kegg
3,4',5,7-Tetrahydroxy-3'-methoxyflavone	MeSH
Iso-rhamnetin	MeSH
Isorhamnetine	MeSH
3-Methyl-quercetin	MeSH
Isorhamnetin	MeSH
3,4',5,7-Tetrahydroxy-3'-methoxy-flavone	MeSH
3-Methylquercetin	MeSH

Chemical Formula

C₁₆H₁₂O₇

Average Molecular Weight

316.2623

Monoisotopic Molecular Weight

316.058302738

IUPAC Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-methoxy-4H-chromen-4-one

Traditional Name

quercetin 3-methyl ether

CAS Registry Number

1486-70-0

SMILES

COC1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C16H12O7/c1-22-16-14(21)13-11(20)5-8(17)6-12(13)23-15(16)7-2-3-9(18)10(19)4-7/h2-6,17-20H,1H3

InChI Key

WEPBGSIAWZTEJR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

3-O-methylated flavonoids

Alternative Parents

Substituents

3-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
3-methoxychromone
Chromone
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Ether
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monomethoxyflavone (CHEBI:16860 )
tetrahydroxyflavone (CHEBI:16860 )
flavonols (C04443 )
Flavones and Flavonols (LMPK12112729 )

Functional Ontology

Not Available

Exogenous (FooDB: )

Food

Pulse

Bean

Common bean (FooDB: FOOD00134)

Process

Not Available

Role

Industrial application

Antiviral agent (FooDB: )

Pharmaceutical industry

Antineoplastic agent

Cancer preventive (FooDB: )

Agriculture

Pesticide (FooDB: )

Biological role

Anti histaminic (FooDB: )
Anti-inflammatory (FooDB: )
Anti rhinoviral (FooDB: )

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.68	ALOGPS
logP	2.27	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	6.38	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	81.61 m³·mol⁻¹	ChemAxon
Polarizability	30.49 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon