ChemFOnt: Showing chemical card for Butein (CFc000332864)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:12:24 UTC

Chemfont ID

CFc000332864

Molecule Identification

Common Name

Butein

Definition

Butein, also known as 2',3,4,4'-tetrahydroxychalcone, is a member of the class of compounds known as 2'-hydroxychalcones. 2'-hydroxychalcones are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, butein is considered to be a flavonoid lipid molecule. Butein is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Butein is a bitter tasting compound found in broad bean, which makes butein a potential biomarker for the consumption of this food product. Butein is a chalcone of the chalconoids. It can be found in Toxicodendron vernicifluum (or formerly Rhus verniciflua), Dahlia, Butea (Butea monosperma) and Coreopsis It has antioxidative, aldose reductase and advanced glycation endproducts inhibitory effects. It is also a sirtuin-activating compound, a chemical compound having an effect on sirtuins, a group of enzymes that use NAD+ to remove acetyl groups from proteins. It turned out that buteins possess a high ability to inhibit aromatase process in the human body, for this reason, the use of these compounds in the treatment of breast cancer on the estrogen ground has been taken into account. The first attempts of sport pro-hormone supplementation with the use of buteins took place in Poland .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(e)-2',3,4,4'-Terahydroxychalcone	ChEBI
2',3,4,4'-Tetrahydroxychalcone	ChEBI
3,4,2',4'-Tetrahydroxychalcone	ChEBI
2',4',3,4-Tetrahydroxychalcone	MeSH

Chemical Formula

C₁₅H₁₂O₅

Average Molecular Weight

272.2528

Monoisotopic Molecular Weight

272.068473494

IUPAC Name

(2E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one

Traditional Name

butein

CAS Registry Number

487-52-5

SMILES

OC1=CC(O)=C(C=C1)C(=O)\C=C\C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C15H12O5/c16-10-3-4-11(14(19)8-10)12(17)5-1-9-2-6-13(18)15(20)7-9/h1-8,16,18-20H/b5-1+

InChI Key

AYMYWHCQALZEGT-ORCRQEGFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxychalcones

Alternative Parents

Substituents

2'-hydroxychalcone
Cinnamylphenol
Hydroxycinnamic acid or derivatives
Benzoyl
Catechol
Aryl ketone
Styrene
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Acryloyl-group
Enone
Vinylogous acid
Alpha,beta-unsaturated ketone
Ketone
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

chalcones (CHEBI:3237 )
chalcones (C08578 )
Chalcones and dihydrochalcones (C08578 )
Chalcones and dihydrochalcones (LMPK12120111 )

Functional Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Disposition

Source

Exogenous

Exogenous (FooDB: )

Food

Pulse

Bean

Broad bean (FooDB: FOOD00197)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Flavonoid Biosynthesis (PathBank: SMP0012021)

Role

Industrial application

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Antioxidant (FooDB: )
Antioxidant (FooDB: )

Coloring agent

Pigment (FooDB: )
Pigment (FooDB: )

Biological role

Anti-inflammatory (FooDB: )

Modulator

Inhibitor

Enzyme inhibitor

Oxidase inhibitor (FooDB: )

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.074 g/L	ALOGPS
logP	2.61	ALOGPS
logP	3.33	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	7.11	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	74.8 m³·mol⁻¹	ChemAxon
Polarizability	27.48 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon