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| | XANTHOHUMOL Basic information |
| Product Name: | XANTHOHUMOL | | Synonyms: | XANTHOHUMOL;XANTHOHUMOL, HUMULUS LU PULUS;2',4',4-TRIHYDROXY-6'-METHOXY-3'-PRENYLCHALCONE;(2E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one;XanthohuMo;Xanthohumol from hop (Humulus lupulus);1-(2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one;2-Propen-1-one,1-[2,4-dihydroxy-6-Methoxy-3-(3-Methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-,(2E)- | | CAS: | 6754-58-1 | | MF: | C21H22O5 | | MW: | 354.4 | | EINECS: | 614-078-4 | | Product Categories: | Flavaniods;standard material,plant extracts;SiChem | | Mol File: | 6754-58-1.mol |  |
| | XANTHOHUMOL Chemical Properties |
| Melting point | 157-159℃ | | Boiling point | 576.5±50.0 °C(Predicted) | | density | 1.244 | | storage temp. | 2-8°C | | solubility | ethanol: soluble10mg/mL | | form | powder | | pka | 7.59±0.45(Predicted) | | color | Yellow | | Stability: | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month. | | InChI | 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+ | | InChIKey | ORXQGKIUCDPEAJ-YRNVUSSQSA-N | | SMILES | C(C1=C(OC)C=C(O)C(C/C=C(/C)\C)=C1O)(=O)/C=C/C1=CC=C(O)C=C1 | | LogP | 5.172 (est) |
| Hazard Codes | N,Xi | | Risk Statements | 50/53-43 | | Safety Statements | 60-61-45-22 | | RIDADR | UN 3077 9/PG 3 | | WGK Germany | 3 | | RTECS | UD5574117 | | HS Code | 29145090 |
| | XANTHOHUMOL Usage And Synthesis |
| Description | Xanthohumol (6754-58-1) binds to the N-terminal domain of valosin-containing protein (VCP), an essential protein for autophagosome maturation. Xanthohumol inhibits the function of VCP thereby impairing autophagosome maturation and resulting in accumulation of the microtubule-associated protein 1 light chain 3-II (LC3-II)1. Impairs prostate cancer cell growth and proliferation2. Cell permeable. | | Chemical Properties | Light yellow to Brown powder to crystal. | | Uses | 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
| | Uses | Reference standard in the analysis of herbal medicinal products. | | Application | Xanthohumol is the prenylated chalcone isolated from the female inflorescences of the hop plant (Humulus lupulus L.), an ingredient of beer, have long been used in traditional medicine. Xanthohumol is one of the bioactive substances, and has been reported that it has various pharmacological activities, including antioxidant, anti-inflammatory, anti-proliferative, and osteogenic effects. | | Definition | ChEBI: A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4', a methoxy group at position 6' and a prenyl group at position 3'. Isolated from Humulus lupulus, it induces apo
tosis in human malignant glioblastoma cells. | | General Description | Produced and qualified by HWI pharma services GmbH.
Exact content by quantitative NMR can be found on the certificate. | | 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. | | storage | Store at +4°C | | References | 1) Sasazawa et al. (2012), Xanthohumol impairs autophagosome maturation through direct inhibition of valosin-containing protein; ACS Chem. Biol., 7 892
2) Vene et al. (2012), Xanthohumol impairs prostate cancer cell growth and invasion and diminishes the incidence and progression of advanced tumors in TRAMP mice; Mol. Med., 18 1292 |
| | XANTHOHUMOL Preparation Products And Raw materials |
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