Xanthohumol

Xanthohumol
Names
	IUPAC name (E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Identifiers
CAS Number	6754-58-1 =;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:66331 ;
ChEMBL	ChEMBL253896 ;
ChemSpider	555077 ;
ECHA InfoCard	100.123.285
PubChem CID	639665;
RTECS number	UD5574117;
UNII	T4467YT1NT ;
CompTox Dashboard (EPA)	DTXSID00893171 ;
	InChI InChI=1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+ Key: ORXQGKIUCDPEAJ-YRNVUSSQSA-N ;
	SMILES O=C(c1c(OC)cc(O)c(c1O)C/C=C(\C)C)\C=C\c2ccc(O)cc2;
Properties
Chemical formula	C21H22O5
Molar mass	354.402 g·mol−1
Density	1.24 g/cm3
Melting point	157–159 °C (315–318 °F; 430–432 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Xanthohumol is a prenylated chalconoid from hops and beer. This prenylated chalconoid is not estrogenic. It has a range of biological properties in animal studies, though only at doses significantly higher than are available in natural sources,^[2] and may have potential therapeutic utility.^[3]^[4]

References

^ ^a ^b Xanthohumol from hop (Humulus lupus), Santa Cruz Biotechnology
^ "Study: Main Ingredient Found In Beer Can Help Improve Memory". CBS Seattle. September 30, 2014. The researchers point out that they gave the mice huge quantities of xanthohumol as dietary supplements and caution people shouldn't start drinking lots of beer to improve their memories ... A human would have to drink 2000 liters of beer a day to reach the xanthohumol levels we used in this research
^ Magalhães, P. J.; Carvalho, D. O.; Cruz, J. M.; Guido, L. F.; Barros, A. A. (2009). "Fundamentals and health benefits of xanthohumol, a natural product derived from hops and beer". Natural product communications. 4 (5): 591–610. PMID 19445313.
^ Stevens JF, Page JE (May 2004). "Xanthohumol and related prenylflavonoids from hops and beer: to your good health!". Phytochemistry. 65 (10): 1317–30. doi:10.1016/j.phytochem.2004.04.025. PMID 15231405. {{cite journal}}: Cite has empty unknown parameter: |1= (help)

Template:Natural-phenol-stub

[scbt-1] Xanthohumol from hop (Humulus lupus), Santa Cruz Biotechnology

[2] "Study: Main Ingredient Found In Beer Can Help Improve Memory". CBS Seattle. September 30, 2014. The researchers point out that they gave the mice huge quantities of xanthohumol as dietary supplements and caution people shouldn't start drinking lots of beer to improve their memories ... A human would have to drink 2000 liters of beer a day to reach the xanthohumol levels we used in this research

[3] Magalhães, P. J.; Carvalho, D. O.; Cruz, J. M.; Guido, L. F.; Barros, A. A. (2009). "Fundamentals and health benefits of xanthohumol, a natural product derived from hops and beer". Natural product communications. 4 (5): 591–610. PMID 19445313.

[pmid15231405-4] Stevens JF, Page JE (May 2004). "Xanthohumol and related prenylflavonoids from hops and beer: to your good health!". Phytochemistry. 65 (10): 1317–30. doi:10.1016/j.phytochem.2004.04.025. PMID 15231405. {{cite journal}}: Cite has empty unknown parameter: |1= (help)

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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

See also

References