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Merck
CN

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:
6754-58-1
Molecular Weight:
354.40
NACRES:
NA.24
PubChem Substance ID:
329747218
UNSPSC Code:
85151701
MDL number:
MFCD00210576

Key Documents

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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+

SMILES string

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

InChI key

ORXQGKIUCDPEAJ-YRNVUSSQSA-N

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

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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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
HWI00080-3
HWI00080-2
HWI00080-1

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Yongbo Liu et al.
Journal of experimental therapeutics & oncology, 10(1), 1-8 (2012-09-06)
Xanthohumol (XN), a prenylated chalcone present in hops exhibits anti-inflammatory, antioxidant and anticancer activity. In the present study we show that XN inhibits the proliferation of mouse lymphoma cells and IL-2 induced proliferation and cell cycle progression in mouse splenic
Pawel Zmora et al.
Archives of animal nutrition, 66(1), 66-71 (2012-03-09)
There is a great interest in reducing the methane emission from ruminants as one possible cause of global warming. The aim of the presented study was to determine the effects of xanthohumol, one of the hop (Humulus lupulus) phytofactors, on
J Rudzitis-Auth et al.
Human reproduction (Oxford, England), 27(6), 1735-1744 (2012-03-27)
Xanthohumol is a prenylated flavonoid isolated from hops, which is known to act as a pleiotropic cancer chemopreventive agent owing to its anti-proliferative, anti-inflammatory and anti-angiogenic properties. In the present study, we analyzed, for the first time, whether this dietary
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
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
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