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Xanthohumol COX inhibitor

Name: Xanthohumol
Brand: Selleck Chemicals
SKU: S7889
Rating: 5 (12 reviews)

Cat.No.S7889

Xanthohumol, a prenylated chalcone from hop, inhibits COX-1 and COX-2 activity and shows chemopreventive effects. This compound inhibits diacylglycerol acyltransferase 1 (DGAT1) and DGAT2 with both IC50 of 40 μM. It is also a potent antiviral agent against a series of DNA and RNA viruses. This chemical induces growth inhibition and apoptosis in cancer cells. Phase 1.

Chemical Structure

Molecular Weight: 354.4

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Quality Control

Batch: Purity: 99.93%

99.93

Related Targets	Dehydrogenase HSP Transferase P450 (e.g. CYP17) PDE phosphatase PPAR Vitamin Carbohydrate Metabolism Mitochondrial Metabolism
Other COX Inhibitors	NS-398 (NS398) Paeoniflorin (NSC 178886) Lumiracoxib Bufexamac Nimesulide Ginsenoside Rd Pranoprofen Phenacetin Tolfenamic Acid (-)-Epicatechin gallate

Chemical Information, Storage & Stability

Molecular Weight	354.4	Formula	C₂₁H₂₂O₅	Storage (From the date of receipt)	3 years-20°Cpowder
CAS No.	6754-58-1	Download SDF		Storage of Stock Solutions	1 year-80°Cin solvent 1 month-20°Cin solvent
Synonyms	N/A			Smiles	CC(=CCC1=C(C(=C(C=C1O)OC)C(=O)C=CC2=CC=C(C=C2)O)O)C

Solubility

In vitro
Batch:

DMSO : 70 mg/mL (197.51 mM)
(Moisture-contaminated DMSO may reduce solubility. Use fresh, anhydrous DMSO.)

Ethanol : 70 mg/mL

Water : Insoluble

Molarity Calculator

Mass	Concentration	Volume	Molecular Weight
=	×	×

Dilution Calculator Molecular Weight Calculator

In vivo Batch:
Homogeneous suspension	CMC-NA	≥5mg/ml	Taking the 1 mL working solution as an example, add 5 mg of this product to 1 ml of CMC-Na solution, mix evenly to obtain a homogeneous suspension with a final concentration of 5 mg/ml.
Homogeneous suspension	CMC-NA	≥5mg/ml	Taking the 1 mL working solution as an example, add 5 mg of this product to 1 ml of CMC-Na solution, mix evenly to obtain a homogeneous suspension with a final concentration of 5 mg/ml.
Clear solution	5% DMSO 1 40% PEG 300 2 5% Tween 80 3 ddH2O Validated by Selleck labs. Should you need adjustments to this formulation, contact our sales team for custom testing.	2.500mg/ml (7.05mM)	Taking the 1 mL working solution as an example, add 50 μL of 50 mg/ml clear DMSO stock solution to 400 μL of PEG300, mix evenly to clarify it; add 50 μL of Tween80 to the above system, mix evenly to clarify it; then continue adding Adjust the volume to 1 mL with 500 μL ddH2O. The mixed solution should be used immediately for optimal results.
Homogeneous suspension	CMC-NA	≥5mg/ml	Taking the 1 mL working solution as an example, add 5 mg of this product to 1 ml of CMC-Na solution, mix evenly to obtain a homogeneous suspension with a final concentration of 5 mg/ml.
Homogeneous suspension	CMC-NA	≥5mg/ml	Taking the 1 mL working solution as an example, add 5 mg of this product to 1 ml of CMC-Na solution, mix evenly to obtain a homogeneous suspension with a final concentration of 5 mg/ml.

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal making an allowance for loss during the experiment)

Dosage: mg/kg Average weight of animals: g Dosing volume per animal:μL Number of animals:

Step 2: Enter the in vivo formulation (This is only the calculator, not formulation. Please contact us first if there is no in vivo formulation at the solubility Section.)

% DMSO + % + % Tween 80 + % ddH₂O

%DMSO+ %

Calculation results:

Working concentration: mg/ml;

Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid 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 master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH₂O, mix and clarify.

Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.

Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.

Mechanism of Action

Targets/IC₅₀/Ki	COX-1 COX-2 DGAT1 (Cell-free assay) 40 μM DGAT2 (Cell-free assay) 40 μM
In vitro	Xanthohumol inhibits Cyp1A activity and induces QR activity in mouse hepatoma cell culture. This compound scavenges reactive oxygen species and inhibits superoxide anion radical and nitric oxide production. In addition, it prevents carcinogenesis via inhibition of DNA synthesis and induction of cell cycle arrest in S phase, apoptosis, and cell differentiation. It shows potent anti-HIV-1 activity.
Kinase Assay	Inhibition of COX Activity
Kinase Assay	Inhibition of COX-1 activity is measured by monitoring oxygen consumption during the conversion of arachidonic acid to PGs using a Clark-type O2-electrode. The reaction mixture contains ~0.2 units COX-1 in 100 μL of microsome fraction derived from ram seminal vesicles as a crude source of COX-1 (specific activity 0.2–1 units/mg protein) or 0.23 units of recombinant human COX-2 (specific activity 43 units/mg protein). For calculation, the rate of O2 consumption is compared with a DMSO control (100% activity). CP-16171, a nonsteroidal anti-inflammatory drug, is used as positive inhibitory substance for COX-1 activity with an IC50 of 0.35 ± 0.05 μM (n = 2). Alternatively, nimesulide, a COX-2 specific inhibitor, inhibits COX-2 activity by 52 ± 5.7% (n = 2) at a concentration of 50 μM.
In vivo	In CETP-Tg mice, Xanthohumol (p.o.) prevents cholesterol accumulation leading to atherosclerosis. In TRAMP mice, this compound induces a decrease in the average weight of the urogenital (UG) tract, delays advanced tumour progression and inhibits the growth of poorly differentiated prostate carcinoma.
References	[1] https://pubmed.ncbi.nlm.nih.gov/12481418/ [2] https://pubmed.ncbi.nlm.nih.gov/15550272/ [3] https://pubmed.ncbi.nlm.nih.gov/23166663/ [4] https://pubmed.ncbi.nlm.nih.gov/22952060/ [5] https://pubmed.ncbi.nlm.nih.gov/19132064/

Clinical Trial Information

(data from https://clinicaltrials.gov, updated on 2024-05-22)

NCT Number	Recruitment	Conditions	Sponsor/Collaborators	Start Date	Phases
NCT06225258	Recruiting	Septic Shock\|Pneumonia\|ARDS	Medical University of Lublin	May 9 2023	Phase 2
NCT03735420	Active not recruiting	Healthy	National University of Natural Medicine\|Oregon State University\|Pacific Northwest National Laboratory	August 12 2019	Phase 1
NCT01367431	Completed	Metabolic Syndrome	Oregon State University\|Oregon Health and Science University\|National Center for Complementary and Integrative Health (NCCIH)	August 2011	--

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