Xanthohumol
- CAS No.
- 6754-58-1
- Chemical Name:
- Xanthohumol
- Synonyms
- XanthohuMo;XANTHOHUMOL;Xantho-Flav;prop-2-en-1-one;Xantho Flav-Pure;Xanthohumol, >99%;Xanthohumol 99.8%;Xanthohumol Standard;Xanthohumol (6CI, 7CI);Xanthohumol Hops Extract
- CBNumber:
- CB5128899
- Molecular Formula:
- C21H22O5
- Molecular Weight:
- 354.4
- MOL File:
- 6754-58-1.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/5/22 17:52:39
| 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) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS07,GHS09 |
|---|---|
| Signal word | Warning |
| Hazard statements | H317-H400 |
| Precautionary statements | P273-P280 |
| 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 price More Price(3)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | X0379 | Xanthohumol from hop (Humulus lupulus) ≥96% (HPLC) | 6754-58-1 | 5MG | ₹31154.35 | 2022-06-14 | Buy |
| TCI Chemicals (India) | X0068 | Xanthohumol | 6754-58-1 | 25MG | ₹29700 | 2022-05-26 | Buy |
| SRL | 94623 | Xanthohumol ex. Hop (Humulus Lupulus), 94% | 6754-58-1 | 5mg | ₹18690 | 2022-05-26 | Buy |
Xanthohumol Chemical Properties,Uses,Production
Description
Xanthohumol(XH, 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) Impairs prostate cancer cell growth and proliferation Cell permeable.
Chemical Properties
Xanthohumol is a Light yellow to Brown powder to crystal. It can dissolve in ethanol. This compound is a natural prenylated chalcone isolated from the hop plant, H. lupulus. Xanthohumol and its metabolites induce protective detoxification enzymes, at least in part via the nuclear factor erythroid-2-related factor 2 pathway.
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
Xanthohumol (XN), a prenylated chalcone present in Hop (Humulus lupulus), has been found to possess prominent activities against aging, diabetes, inflammation, microbial infection, and cancer.
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.
Xanthohumol Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| TCI Chemicals (India) Pvt. Ltd. | 1800 425 7889 | New Delhi, India | 6778 | 58 | Inquiry |
| CLEARSYNTH LABS LTD. | +91-22-45045900 | Hyderabad, India | 6351 | 58 | Inquiry |
| A.J Chemicals | 91-9810153283 | New Delhi, India | 6124 | 58 | Inquiry |
| Sisco Research Laboratories Pvt. Ltd. | +91-22-4268 5800 | Mumbai, India | 4317 | 58 | Inquiry |
| Triveni chemicals | 08048762458 | New Delhi, India | 6093 | 58 | Inquiry |
| Nanjing Sky Hope Tongyuan Biological Engineering Co., Ltd. | +86-0086-025-69916489 +86-18852044786 | China | 323 | 58 | Inquiry |
| ZhenYiBio Technology Inc | +8615309206328 | China | 298 | 58 | Inquiry |
| Hebei Kingfiner Technology Development Co.Ltd | +86-15532196582 +86-15373005021 | China | 2989 | 58 | Inquiry |
| Henan Fengda Chemical Co., Ltd | +86-371-86557731 +86-13613820652 | China | 20294 | 58 | Inquiry |
| Hangzhou FandaChem Co.,Ltd. | 008657128800458; +8615858145714 | China | 9337 | 55 | Inquiry |