Merck
  • X0379
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X0379

Sigma-Aldrich

Xanthohumol from hop (Humulus lupulus)

≥96% (HPLC)

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
Empirical Formula (Hill Notation):
C21H22O5
CAS Number:
Molecular Weight:
354.40
MDL-Nummer:
PubChem Substanz-ID:
NACRES:
NA.77

Biologische Quelle

plant (Humulus lupulus)

Qualitätsniveau

Assay

≥96% (HPLC)

Form

powder

mp (Schmelzpunkt)

172 °C

Löslichkeit

ethanol: 10 mg/mL

Lagertemp.

2-8°C

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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This Item
G0549G8761G1660
Corosolic acid from Lagerstroemia speciosa ≥98% (HPLC)

Sigma-Aldrich

G0549

Corosolsäure

biological source

plant (Humulus lupulus)

biological source

-

biological source

-

biological source

plant (Ungeria victoris)

assay

≥96% (HPLC)

assay

≥98% (HPLC)

assay

≥95% (HPLC)

assay

≥94% (HPLC)

form

powder

form

powder

form

-

form

powder

mp

172 °C

mp

-

mp

-

mp

270 °C

solubility

ethanol: 10 mg/mL

solubility

methanol: 1 mg/mL, clear, colorless

solubility

-

solubility

DMSO: soluble 10 mg/mL, clear, colorless, water: soluble 20 mg/mL, clear, colorless

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

Allgemeine Beschreibung

Xanthohumol is a chalcone compound present in the female inflorescence of hop (Humulus lupulus) plant. It is a food additive.

Anwendung

Xanthohumol from hop (Humulus lupulus) has been used:
  • to treat glioblastoma cells to test its effect on inducing apoptosis
  • to test its protective effect in renal ischemia/reperfusion (I/R) injury
  • as a component of Dulbecco′s modified Eagle medium (DMEM) to test its antiviral activity in Huh7.5 cells infected with hepatitis C virus cell culture (HCVcc) system

Biochem./physiol. Wirkung

Prenylated flavonoids such as xanthohumol have antiproliferative and cytotoxic effects in human cancer cell lines. Xanthohumol protected HepG2 cells against benzo[a]pyrene and related carcinogens. It also protected against reactive oxygen species (ROS), not by a direct anti-oxidant effect, but instead mediated by induction of cellular defense mechanisms against oxidative stress.Xanthohumol inhibits diacylglycerol acetyltransferase (DGAT) and human P450 enzymes. It also inhibits the expression of HIF-1α and VEGF under hypoxic conditions.
Xanthohumol induces apoptosis in glioma cancer by modulating microRNA based network. It exhibits anti-inflammatory property by inhibiting janus kinases (JAKs), signal transducer and activator of transcription proteins (STATs). Xanthohumol elicits antiviral functionality against bovine viral diarrhea virus (BVDV) and anti-hepatitis C virus in vitro. It also induces autophagy and has antiplatelet and neuroprotective effects. Xanthohumol also regulates various metabolic processes including the inhibition of triglyceride formation, atherosclerotic plaque and adipogenesis.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt F

Not applicable

Flammpunkt C

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves


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