Butein

Butein
Names

IUPAC name (E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one
Other names 2',3,4,4'-Tetrahydroxychalcone 2',4',3,4-Tetrahydroxychalcone 3,4,2',4'-Tetrahydroxychalcone 2′,4′,3,4-Tetrahydroxychalcone
Identifiers
CAS Number	487-52-5^Y 21849-70-7
ChEMBL	ChEMBL128000^Y
ChemSpider	4444634^Y
Jmol interactive 3D	Image
PubChem	5281222
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+^Y Key: AYMYWHCQALZEGT-ORCRQEGFSA-N^Y InChI=1/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+ Key: AYMYWHCQALZEGT-ORCRQEGFBV
SMILES C1=CC(=C(C=C1C=CC(=O)C2=C(C=C(C=C2)O)O)O)O
Properties
Chemical formula	C₁₅H₁₂O₅
Molar mass	272.25 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
Infobox references

Butein is a chalconoid. It can be found in Toxicodendron vernicifluum (or formerly Rhus verniciflua). It has antioxidative, aldose reductase and advanced glycation endproducts inhibitory effects.^[1] 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.^[2] The first attempts of sport pro-hormone supplementation with the use of buteins took place in Poland.^[3]

References

↑ Lee EH, Song DG, Lee JY, Pan CH, Um BH, Jung SH (August 2008). "Inhibitory effect of the compounds isolated from Rhus verniciflua on aldose reductase and advanced glycation endproducts". Biol. Pharm. Bull. 31 (8): 1626–30. doi:10.1248/bpb.31.1626. PMID 18670102.
↑ Wang Y. "The plant polyphenol butein inhibits testosterone-induced proliferation in breast cancer cells expressing aromatase" Life Sci. 2005 May 20;77(1):39-51.
↑ S.Amboziak "Aromatase in the dock" 09.2012

Chalconoids and their glycosides

Chalconoids	Butein Isoliquiritigenin Methyl hydroxychalcone Okanin

Chalconoid glycosides	Carthamin Marein okanin 3,4,3′-trimethyl ether 4′-glucoside okanin 4-methyl ether 4′-glucoside okanin 4-methyl ether 4′-glucoside monoacetate Okanin 3,4-dimethyl ether 4′-glucoside

Acylated chalconoids	Licochalcone A Sophoradin (prenylated) Tephrospinosin (3′,5′-diisopentenyl-2′,4′-dihydroxychalcone) (prenylated) Xanthohumol (prenylated)

O-methylated chalconoids	Cardamomin Flavokawin B Okanin 3,4,3′,4′-tetramethyl ether Pashanone (2',6'-Dihydroxy-3',4'-dimethoxychalcone)

Flavokavains	Flavokavain A Flavokavain B Flavokavain C

Synthetic	Sofalcone

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