ChemFOnt: Showing chemical card for Tetramethylquercetin (CFc000336207)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:29:12 UTC

Chemfont ID

CFc000336207

Molecule Identification

Common Name

Tetramethylquercetin

Definition

Retusin(ariocarpus), also known as 5-hydroxy-3,7,3',4'-tetramethoxyflavone or 3,7,3',4'-tetra-O-methylquercetin, is a member of the class of compounds known as 7-o-methylated flavonoids. 7-o-methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, retusin(ariocarpus) is considered to be a flavonoid lipid molecule. Retusin(ariocarpus) is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Retusin(ariocarpus) can be found in common oregano and mandarin orange (clementine, tangerine), which makes retusin(ariocarpus) a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(3,4-Dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-1-benzopyran-4-one	ChEBI
3,3',4',7-O-Tetramethylquercetin	ChEBI
3,3',4',7-Tetramethylquercetin	ChEBI
3,7,3',4'-Tetramethylquercetin	ChEBI
Quercetin 3,3',4',7-tetramethyl ether	ChEBI
Quercetin 3,7,3',4'-tetramethyl ether	ChEBI
Retusin	ChEBI
Retusine	ChEBI
5-Hydroxy-3,7,3',4'-tetramethoxyflavone	MetaCyc, MeSH
3,7,3',4'-Tetra-O-methylquercetin	MetaCyc

Chemical Formula

C₁₉H₁₈O₇

Average Molecular Weight

358.342

Monoisotopic Molecular Weight

358.10525293

IUPAC Name

2-(3,4-dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-chromen-4-one

Traditional Name

retusin (flavonol)

CAS Registry Number

1245-15-4

SMILES

COC1=CC(O)=C2C(=O)C(OC)=C(OC2=C1)C1=CC=C(OC)C(OC)=C1

InChI Identifier

InChI=1S/C19H18O7/c1-22-11-8-12(20)16-15(9-11)26-18(19(25-4)17(16)21)10-5-6-13(23-2)14(7-10)24-3/h5-9,20H,1-4H3

InChI Key

HHGPYJLEJGNWJA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

3p-methoxyflavonoid-skeleton
3-methoxyflavonoid-skeleton
4p-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
5-hydroxyflavonoid
3-methoxychromone
Chromone
1-benzopyran
Benzopyran
Dimethoxybenzene
O-dimethoxybenzene
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
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

Flavones and Flavonols (LMPK12112770 )

Functional Ontology

Not Available

Exogenous (FooDB: )

Food

Fruit

Citrus

Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)

Herb and spice

Herb

Common oregano (FooDB: FOOD00124)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Antineoplastic agent

Antitumor (FooDB: )

Biological role

Cytotoxic (FooDB: )

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.02 g/L	ALOGPS
logP	3.31	ALOGPS
logP	2.71	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	8.36	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.45 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	95.06 m³·mol⁻¹	ChemAxon
Polarizability	36.66 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