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01130595

Xanthohumol

primary reference standard

Synonym(s):

(E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)propenone, 2′,4,4′-Trihydroxy-6′-methoxy-3′-prenylchalcone

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About This Item

Empirical Formula (Hill Notation):
C21H22O5
CAS Number:
Molecular Weight:
354.40
MDL number:
UNSPSC Code:
85151701
PubChem Substance ID:
NACRES:
NA.24

grade

primary reference standard

shelf life

limited shelf life, expiry date on the label

manufacturer/tradename

HWI

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

food and beverages

SMILES string

COc1cc(O)c(C\C=C(/C)C)c(O)c1C(=O)\C=C\c2ccc(O)cc2

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+

InChI key

ORXQGKIUCDPEAJ-YRNVUSSQSA-N

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General description

Produced and qualified by HWI pharma services GmbH.
Exact content by quantitative NMR can be found on the certificate.

Application

Reference standard in the analysis of herbal medicinal products.

Other Notes

This compound is commonly found in plants of the genus: humulus

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Christoph Dorn et al.
Experimental and molecular pathology, 94(1), 10-16 (2012-05-29)
Liver ischemia/reperfusion (I/R) leads to formation of reactive oxygen species (ROS), which cause hepatic injury and initiate an inflammatory response, which is a critical problem after liver surgery and transplantation. Xanthohumol, the major prenylated chalcone found in hops, has been
M Motyl et al.
Die Pharmazie, 67(1), 91-94 (2012-03-08)
Xanthohumol, the most abundant prenylated chalcone in hop (Humulus lupulus L.) cones, is well known to exert several promising pharmacological activities in vitro and in vivo. Among these, the chemopreventive, anti-inflammatory and anti-cancer effects are probably the most interesting. As
Roberto Benelli et al.
Biochemical pharmacology, 83(12), 1634-1642 (2012-03-27)
Although the vast majority of patients with acute lymphocytic leukemia (ALL) attain remission with modern therapies, relapsed leukemia will continue to be a common malignancy both in childhood and in adults, until new treatments are available. Therapeutic options for advanced
Carmen Pinto et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 50(10), 3405-3412 (2012-08-14)
Xanthohumol (XN), a prenyl flavonoid present in beer, prevents the acute hepatic injury induced by carbon tetrachloride (CCl4) in rats. Pre-treatment of rats with XN significantly reduced the increased liver weight observed in CCl4-intoxicated rats, normalised the increased values of
Thomas E Ceremuga et al.
AANA journal, 81(3), 193-198 (2013-08-09)
The purpose of this study was to investigate the anxiolytic effects of xanthohumol, a component of Humulus lupulus (hops), and its potential interaction with the benzodiazepine binding site on the y-aminobutyric acid (GABAA) receptor in the male Sprague-Dawley rat. This

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