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X0379 Sigma-Aldrich

Xanthohumol from hop (Humulus lupulus)

≥96% (HPLC)

  • CAS Number 6754-58-1

  • Empirical Formula (Hill Notation) C21H22O5

  • Molecular Weight 354.40

  •  MDL number MFCD00210576

  •  PubChem Substance ID 24902121

  •  NACRES NA.77



Related Categories Biochemicals and Reagents, Cell Biology, D to K, Diacylglycerol acetyltransferase, Enzyme Inhibitors,
Quality Level   200
biological source   plant (Humulus lupulus)
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+


General description

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


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


5 mg in glass bottle

Biochem/physiol Actions

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.

Safety & Documentation

Safety Information

Personal Protective Equipment 
UN 3077 9 / PGIII
WGK Germany 
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable


Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles


NF-κB and Inflammation

Chronic inflammation is an underlying factor in the development and progression of many of the chronic diseases of aging, such as arthritis, atherosclerosis, diabetes, and cancer. Oxidative cellular ...
BioFiles 2007, 2.4, 14.
Keywords: Acetylations, Adhesion, Angiogenesis, Apoptosis, Cancer, Carcinogens, Catalysis, Cell culture, Cell proliferation, Cell signaling, Cellular processes, Degradations, Diabetes, Diseases, Environmental, Gene expression, Glycosylations, High performance liquid chromatography, Inflammation, PAGE, Phosphorylations, Thin layer chromatography, Transcription, transformation

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Peer-Reviewed Papers


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