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X0379

Xanthohumol

powder, ≥96% (HPLC)

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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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Size/SKUAvailabilityPrice
5 mg
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$391.00

About This Item

Empirical Formula (Hill Notation):
C21H22O5
CAS Number:
6754-58-1
Molecular Weight:
354.40
UNSPSC Code:
12352204
PubChem Substance ID:
24902121
NACRES:
NA.77
MDL number:
MFCD00210576

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Product Name

Xanthohumol from hop (Humulus lupulus), ≥96% (HPLC)

biological source

plant (Humulus lupulus)

Quality Segment

200

assay

≥96% (HPLC)

form

powder

mp

172 °C

solubility

ethanol: 10 mg/mL

storage temp.

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

General description

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

Application

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 Actions

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.
Prenylated flavonoids such as xanthohumol have antiproliferative and cytotoxic effects in human cancer cell lines. Xanthohumol inhibits diacylglycerol acetyltransferase (DGAT) and human P450 enzymes. It also inhibits the expression of HIF-1α and VEGF under hypoxic conditions.
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.

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This Item
PHL8923401130595SML3107
Xanthohumol from hop (Humulus lupulus) ≥96% (HPLC)

Sigma-Aldrich

X0379

Xanthohumol from hop (Humulus lupulus)

Isoxanthohumol phyproof® Reference Substance

PHL89234

Isoxanthohumol

Xanthohumol primary reference standard

01130595

Xanthohumol

Glycycoumarin ≥98% (HPLC)

Sigma-Aldrich

SML3107

Glycycoumarin

description

≥96% (HPLC)

description

phyproof® Reference Substance

description

primary reference standard

description

≥98% (HPLC)

biological source

plant (Humulus lupulus)

biological source

-

biological source

-

biological source

-

assay

≥96% (HPLC)

assay

≥95.0% (HPLC)

assay

-

assay

≥98% (HPLC)

Quality Level

200

Quality Level

-

Quality Level

-

Quality Level

100

form

powder

form

powder

form

-

form

powder

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

storage temp.

−20°C

solubility

ethanol: 10 mg/mL

solubility

-

solubility

-

solubility

DMSO: 2 mg/mL, clear

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves

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    Certificates of Analysis (COA)

    Lot/Batch Number
    0000428063
    0000442006
    0000473957
    0000478812
    0000563264

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