Size | Price | Stock | Qty |
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5mg |
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10mg |
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25mg |
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50mg |
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100mg |
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250mg |
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500mg |
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Other Sizes |
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Purity: ≥98%
Xanthohumol, a naturally occuring prenylated chalcone compound isolated from hops (the female inflorescences of Humulus lupulus), is an inhibitor of COX-1 and COX-2 enzymatic activity and shows chemopreventive effects as well as anti-cancer and anti-angiogenic activities. It binds to the N domain of VCP, suppressing function and impairing autophagosome maturation. It inhibits growth of a wide variety of human cancer cell lines by inhibiting proliferation and inducing apoptosis. Xanthohumol is one of the principal flavonoids isolated from hops, the inhibitor of diacylglycerol acetyltransferase (DGAT), COX-1 and COX-2, and shows anti-cancer and anti-angiogenic activities.
ln Vitro |
ADP-induced blood platelet aggregation is markedly inhibited by xanthohumol, which also dramatically lowers fibrinogen receptor expression (the activated form of GPIIbIIIa) on the surface of platelets[1]. In control myocytes and in cells exposed to Ca2+ overload brought on by: (1) exposure to low K+ solutions; (2) periods of high frequency electrical stimulation; (3) exposures to isoproterenol; or (4) caffeine, xanthohumol (5-50 nM) decreases the frequency of spontaneously occurring Ca2+ sparks and Ca2+ waves. Without inhibiting ICa, xanthohumol (50–100 nM) lowers the rate of relaxation of electrically or caffeine-triggered Ca2+ transients; however, this action is negligible and isoproterenol reverses it at physiological temperatures. Additionally, xanthohumol reduces the SR's rate of recirculation and Ca2+ content[2]. When Xanthohumol is applied to endothelial cells, AMPK phosphorylation and activity rise. It has been confirmed by functional investigations employing biochemical methods that AMPK mediates the anti-angiogenic effect of xanthohumol. Xanthohumol activates AMPK through the action of CAMMKβ, not LKB1. By lowering eNOS phosphorylation, Xanthohumol-induced AMPK activation lowers nitric oxide (NO) levels in endothelial cells, according to an analysis of the downstream pathways. Lastly, Xanthohumol's anti-angiogenic action inactivates the AKT pathway apart from AMPK, indicating that these two signaling pathways operate independently of one another[3]. The formation of intracellular ROS contributes to the glioma cell death caused by xanthohumol. Glioma cell death is largely mediated by xanthohumol's suppression of the IGFBP2/AKT/Bcl2 pathway via miR-204-3p targeting[4].
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ln Vivo |
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Animal Protocol |
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References |
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Additional Infomation |
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-).
Xanthohumol is under investigation in clinical trial NCT01367431 (Xanthohumol and Metabolic Syndrome). Xanthohumol has been reported in Humulus lupulus and Capsicum annuum with data available. Xanthohumol is a prenylated flavonoid derived from the female flowers of the hops plant (Humulus lupulus L), with potential chemopreventive and antineoplastic activities. Upon administration, xanthohumol scavenges reactive oxygen species (ROS), thereby preventing DNA damage due to oxidative stress. In addition, xanthohumol is able to increase the expression of phase II cytoprotective enzymes, thereby inactivating carcinogens. This agent exerts anti-inflammatory activity, through the inhibition of inflammation-inducing enzymes, inhibits DNA synthesis, and induces apoptosis of susceptible cancer cells. Xanthohumol also decreases the expression of C-X-C chemokine receptor 4 (CXCR4), thereby preventing cancer cell invasion. |
Molecular Formula |
C21H22O5
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Molecular Weight |
354.4
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Exact Mass |
354.146
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Elemental Analysis |
C, 71.17; H, 6.26; O, 22.57
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CAS # |
6754-58-1
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Related CAS # |
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PubChem CID |
639665
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Appearance |
Yellow to orange solid powder
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Density |
1.2±0.1 g/cm3
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Boiling Point |
576.5±50.0 °C at 760 mmHg
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Melting Point |
157-159ºC
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Flash Point |
203.4±23.6 °C
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Vapour Pressure |
0.0±1.7 mmHg at 25°C
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Index of Refraction |
1.641
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LogP |
5.17
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Hydrogen Bond Donor Count |
3
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Hydrogen Bond Acceptor Count |
5
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Rotatable Bond Count |
6
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Heavy Atom Count |
26
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Complexity |
515
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Defined Atom Stereocenter Count |
0
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SMILES |
O(C([H])([H])[H])C1C([H])=C(C(=C(C=1C(/C(/[H])=C(\[H])/C1C([H])=C([H])C(=C([H])C=1[H])O[H])=O)O[H])C([H])([H])/C(/[H])=C(\C([H])([H])[H])/C([H])([H])[H])O[H]
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InChi Key |
ORXQGKIUCDPEAJ-YRNVUSSQSA-N
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InChi Code |
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+
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Chemical Name |
(E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
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Synonyms |
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HS Tariff Code |
2934.99.9001
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Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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Solubility (In Vitro) |
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Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (5.87 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (5.87 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: 0.05% (w+w) xanthohumol powder in diet, or suspended in ethanol (2.5 mg+mL): 13mg/mL |
Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
1 mM | 2.8217 mL | 14.1084 mL | 28.2167 mL | |
5 mM | 0.5643 mL | 2.8217 mL | 5.6433 mL | |
10 mM | 0.2822 mL | 1.4108 mL | 2.8217 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration: mg/mL;
Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
NCT06225258 | Recruiting | Dietary Supplement: Xanthohumol | Septic Shock Pneumonia |
Medical University of Lublin | May 9, 2023 | Phase 2 |
NCT05524714 | Completed | Dietary Supplement: solubilized Xanthohumol low dose |
Plasmakinetics of Xanthohumol | University of Bonn | August 1, 2022 | Not Applicable |
NCT05711212 | Recruiting | Dietary Supplement: micellar solubilized Xanthohumol |
Resting Energy Expenditure | University of Bonn | February 15, 2023 | Not Applicable |
NCT03735420 | Active, not recruiting Has Results |
Drug: Xanthohumol Drug: Placebo oral capsule |
Healthy | National University of Natural Medicine | August 12, 2019 | Phase 1 |
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