ChemFOnt: Showing chemical card for Gardenin B (CFc000281670)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:33:17 UTC

Chemfont ID

CFc000281670

Molecule Identification

Common Name

Gardenin B

Definition

Gardenin b, also known as demethyltangeretin or 5-hydroxy-4',6,7,8-tetramethoxyflavone, is a member of the class of compounds known as 8-o-methylated flavonoids. 8-o-methylated flavonoids are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, gardenin b is considered to be a flavonoid lipid molecule. Gardenin b is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Gardenin b can be found in mandarin orange (clementine, tangerine), peppermint, sweet basil, and winter savory, which makes gardenin b a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-Hydroxy-2-(4-methoxyphenyl)-6,7,8-trimethoxy-4H-1-benzopyran-4-one	ChEBI
5-Hydroxy-4',6,7,8-tetramethoxyflavone	ChEBI
Demethyltangeretin	ChEBI
5-Demethyltangeretin	MeSH

Chemical Formula

C₁₉H₁₈O₇

Average Molecular Weight

358.342

Monoisotopic Molecular Weight

358.10525293

IUPAC Name

5-hydroxy-6,7,8-trimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

gardenin B

CAS Registry Number

2798-20-1

SMILES

COC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C(OC)=C2O

InChI Identifier

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

InChI Key

LXEVSYZNYDZSOB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

8-O-methylated flavonoids

Alternative Parents

Substituents

4p-methoxyflavonoid-skeleton
6-methoxyflavonoid-skeleton
8-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Phenol ether
Anisole
Methoxybenzene
Phenoxy compound
Pyranone
Alkyl aryl ether
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monohydroxyflavone (CHEBI:79628 )
tetramethoxyflavone (CHEBI:79628 )
flavones (C15109 )
Flavones and Flavonols (C15109 )
Flavones and Flavonols (LMPK12111451 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302154)

Food

Fruit

Citrus

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

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.023 g/L	ALOGPS
logP	3.07	ALOGPS
logP	2.68	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	9.66	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	94.8 m³·mol⁻¹	ChemAxon
Polarizability	36.75 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