Butein - Misplaced Pages

Butein
Names

Preferred IUPAC name 2′,3,4,4′-Tetrahydroxychalcone
Other names (2E)-1-(2,4-Dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one 2′,4′,3,4-Tetrahydroxychalcone 3,4,2′,4′-Tetrahydroxychalcone
Identifiers
CAS Number	487-52-5
3D model (JSmol)	Interactive image
ChEBI	CHEBI:3237
ChEMBL	ChEMBL128000
ChemSpider	4444634
ECHA InfoCard	100.006.963
KEGG	C08578
PubChem CID	5281222
UNII	4WVS5M0LGF
CompTox Dashboard (EPA)	DTXSID101025569
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+Key: AYMYWHCQALZEGT-ORCRQEGFSA-N 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	272.256 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

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. 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 explored. The first attempts of sport pro-hormone supplementation with the use of buteins took place in Poland.

References

Semwal, R. B., Semwal, D. K., Combrinck, S., & Viljoen, A. (2015). Butein: From ancient traditional remedy to modern nutraceutical. Phytochemistry Letters, 11, 188-201. doi:10.1016/j.phytol.2014.12.014
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

v t e 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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