1.0 2010-04-08 22:04:26 UTC 2025-11-18 22:16:03 UTC FDB000082 Butein 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 . 2',3,4,4'-Tetrahydrochalcone 2',3,4,4'-Tetrahydroxychalcone 2',4',3,4-Tetrahydroxychalcone 3-(3,4-Dihydroxy-phenyl)-1-(2,4-dihydroxy-phenyl)-propenone 3,4,2',4'-Tetrahydroxychalcone Acrylophenone, 2',4'-dihydroxy-3-(3,4-dihydroxyphenyl)- Chalcone, 2',3,4,4'-tetrahydroxy- (7CI,8CI) C15H12O5 272.2528 272.068473494 (2E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one butein 487-52-5 [H]\C(=C(\[H])C1=CC(O)=C(O)C=C1)C(=O)C1=C(O)C=C(O)C=C1 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+ AYMYWHCQALZEGT-ORCRQEGFSA-N 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. 2'-Hydroxychalcones Organic compounds Phenylpropanoids and polyketides Linear 1,3-diarylpropanoids Chalcones and dihydrochalcones Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Acryloyl compounds Aryl ketones Benzoyl derivatives Catechols Cinnamylphenols Enones Hydrocarbon derivatives Hydroxycinnamic acids and derivatives Organic oxides Resorcinols Styrenes Vinylogous acids 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2'-hydroxychalcone Acryloyl-group Alpha,beta-unsaturated ketone Aromatic homomonocyclic compound Aryl ketone Benzenoid Benzoyl Catechol Cinnamylphenol Enone Hydrocarbon derivative Hydroxycinnamic acid or derivatives Ketone Monocyclic benzene moiety Organic oxide Organic oxygen compound Organooxygen compound Phenol Resorcinol Styrene Vinylogous acid Chalcones and dihydrochalcones Chalcones and dihydrochalcones chalcones chalcones logp 2.61 ALOGPS logs -3.57 ALOGPS solubility 7.38e-02 g/l ALOGPS logp 3.33 ChemAxon pka_strongest_acidic 7.11 ChemAxon pka_strongest_basic -6.3 ChemAxon iupac (2E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one ChemAxon average_mass 272.2528 ChemAxon mono_mass 272.068473494 ChemAxon smiles [H]\C(=C(\[H])C1=CC(O)=C(O)C=C1)C(=O)C1=C(O)C=C(O)C=C1 ChemAxon formula C15H12O5 ChemAxon inchi 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+ ChemAxon inchikey AYMYWHCQALZEGT-ORCRQEGFSA-N ChemAxon polar_surface_area 97.99 ChemAxon refractivity 74.8 ChemAxon polarizability 27.48 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 94787 Specdb::MsMs 58194 Specdb::MsMs 58195 Specdb::MsMs 58196 Specdb::MsMs 114072 Specdb::MsMs 114073 Specdb::MsMs 114074 Specdb::MsMs 1479253 Specdb::MsMs 1479351 Broad bean Type 1 specific Vicia faba 3906 0.213 0.351 0.075000001 mg/100 g bitter Anti-inflammatory 370 A substance that reduces or suppresses inflammation. Anti-oxidant 502 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. Oxidase inhibitor 1184 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Pigment 1227 An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light.