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Merck

01130595

Xanthohumol

primary reference standard

Sinónimos:

(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

Fórmula empírica (notación de Hill):
C21H22O5
Número de CAS:
Peso molecular:
354.40
Número MDL:
Código UNSPSC:
85151701
ID de la sustancia en PubChem:
NACRES:
NA.24

grado

primary reference standard

caducidad

limited shelf life, expiry date on the label

fabricante / nombre comercial

HWI

técnicas

HPLC: suitable
gas chromatography (GC): suitable

aplicaciones

food and beverages

cadena SMILES

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+

Clave InChI

ORXQGKIUCDPEAJ-YRNVUSSQSA-N

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Descripción general

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

Aplicación

Reference standard in the analysis of herbal medicinal products.

Otras notas

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

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable


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Violetta Krajka-Kuźniak et al.
Toxicology in vitro : an international journal published in association with BIBRA, 27(1), 149-156 (2012-10-23)
The aim of this study was to investigate whether xanthohumol may exert chemoprotective activity through the modulation of the nuclear factor erythroid-2-related factor 2 (Nrf2) pathway in immortalized normal THLE-2 hepatocytes and a hepatocellular carcinoma HepG2 cell line. Cells were
Roberta Venè et al.
Molecular medicine (Cambridge, Mass.), 18, 1292-1302 (2012-09-07)
Despite recent advances in understanding the biological basis of prostate cancer, management of the disease, especially in the phase resistant to androgen ablation, remains a significant challenge. The long latency and high incidence of prostate carcinogenesis provides the opportunity to
Gianluigi Lauro et al.
Bioorganic & medicinal chemistry, 20(11), 3596-3602 (2012-04-28)
A small library of phenolic natural compounds belonging to different chemical classes was screened on a panel of targets involved in the genesis and progression of cancer. The re-investigation of their potential activity was achieved through the Inverse Virtual Screening
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
Tomasz Tronina et al.
Bioorganic & medicinal chemistry, 21(7), 2001-2006 (2013-02-26)
Xanthohumol (1) and xanthohumol D (2) were isolated from spent hops. Isoxanthohumol (3) was obtained from xanthohumol by isomerisation in alkaline solution. Six metabolites were obtained as a result of transformation of xanthohumol (1) by selected fungal cultures. Their structures

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