Xanthohumol from hop (Humulus lupulus)
SIGMA/X0379 - ≥96% (HPLC)
Synonym: (E)
CAS Number: 6754-58-1
Empirical Formula (Hill Notation): C21H22O5
Molecular Weight: 354.40
MDL Number: MFCD00210576
Linear Formula: C21H22O5
Product Type: Chemical
| assay | ≥96% (HPLC) |
| biological source | plant (Humulus lupulus) |
| form | powder |
| InChI | 1S/C21H22O5/c1-13(2)4-10- |
| InChI key | ORXQGKIUCDPEAJ-YRNVUSSQSA |
| mp | 172 °C |
| Quality Level | 200  |
| SMILES string | COc1cc(O)c(CC=C(/C)C)c(O |
| solubility | ethanol: 10 mg/mL |
| storage temp. | 2-8°C |
| 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: | 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. |
| 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. |
| General description: | Xanthohumol is a chalcone compound present in the female inflorescence of hop (Humulus lupulus) plant. It is a food additive. |
| Packaging: | 5 mg in glass bottle |
| Hazard Codes | Xi,N |
| Risk Statements | 43-50/53 |
| Safety Statements | 22-45-60-61 |
| RIDADR | UN 3077 9 / PGIII |
| WGK Germany | WGK 3 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | ≥96% (HPLC) |
| mp | 172 °C |
| Storage Temp. | 2-8°C |
| UNSPSC | 12352204 |