| Identification | Back Directory | [Name]
XANTHOHUMOL | [CAS]
6754-58-1 | [Synonyms]
XanthohuMo
XANTHOHUMOL
Xantho-Flav
prop-2-en-1-one
Xantho Flav-Pure
Xanthohumol, >99%
Xanthohumol Standard
XANTHOHUMOL, HUMULUS LU PULUS
Hops Flower Extract (Standard)
large stock Xanthohumol 6754-58-1
Xanthohumol from hop (Humulus lupulus)
2',4',4-TRIHYDROXY-6'-METHOXY-3'-PRENYLCHALCONE
1-(2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)
Humulus Lupulus Extract Xanthohumol 6754-58-1 HPLC 95% 98% Yellow Powder
1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-3-(4-hydroxy-phenyl)-propenone
(E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)propenone
1-(2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
(E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
(E)-1-(2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
(2E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one
2-Propen-1-one,1-[2,4-dihydroxy-6-Methoxy-3-(3-Methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-,(2E)- | [EINECS(EC#)]
614-078-4 | [Molecular Formula]
C21H22O5 | [MDL Number]
MFCD00210576 | [MOL File]
6754-58-1.mol | [Molecular Weight]
354.4 |
| Chemical Properties | Back Directory | [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 Information | Back Directory | [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
| [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: Xanthohumol is 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 apoptosis in human malignant glioblastoma cells. It has a role as a metabolite, an apoptosis inducer, an antineoplastic agent, an antiviral agent, an EC 2.3.1.20 (diacylglycerol O-acyltransferase) inhibitor and an anti-HIV-1 agent. It is a member of chalcones, a polyphenol and an aromatic ether. It is a conjugate acid of a xanthohumol(1-). | [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] YUKIKO SASAZAWA. Xanthohumol Impairs Autophagosome Maturation through Direct Inhibition of Valosin-Containing Protein[J]. ACS Chemical Biology, 2012, 7 5: 892-900. DOI:10.1021/cb200492h.
[2] ROBERTA VENè. Xanthohumol impairs human prostate cancer cell growth and invasion and diminishes the incidence and progression of advanced tumors in TRAMP mice.[J]. Molecular Medicine, 2012, 18: 1292-1302. DOI:10.2119/molmed.2012.00174.
[3] VIOLETTA KRAJKA-KU?NIAK Wanda B D Jaros?aw Paluszczak. Xanthohumol induces phase II enzymes via Nrf2 in human hepatocytes in vitro[J]. Toxicology in Vitro, 2013, 27 1: Pages 149-156. DOI:10.1016/j.tiv.2012.10.008.
[4] BIRGIT M. DIETZ Judy L B. Biological reactive intermediates (BRIs) formed from botanical dietary supplements[J]. Chemico-Biological Interactions, 2011, 192 1: Pages 72-80. DOI:10.1016/j.cbi.2010.10.007.
[5] SOSMITHA GIRISA. Xanthohumol from Hop: Hope for cancer prevention and treatment[J]. IUBMB Life, 2021, 73 8: 1016-1044. DOI:10.1002/iub.2522. |
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