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| Targets |
Tetrahydroxymethoxychalcone exhibits activity against several biological targets. It is an inhibitor of pancreatic lipase, an enzyme involved in fat digestion, which suggests potential anti-obesity effects by reducing dietary fat absorption. The compound also has significant free-radical scavenging activity. Additionally, it works by inhibiting the enzyme tyrosinase, which is crucial in the biosynthesis of melanin, suggesting potential applications in cosmetic formulations aimed at skin depigmentation and lightening. The diverse activities are attributed to the presence of multiple phenolic hydroxyl groups, which can donate hydrogen atoms to stabilize free radicals and interact with enzyme active sites.
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| ln Vitro |
Tetrahydroxymethoxychalcone promotes the differentiation and proliferation of myoblasts[1].
In vitro, Tetrahydroxymethoxychalcone has been shown to promote the differentiation and proliferation of myoblasts, suggesting it plays important roles in myogenesis and muscle regeneration. It exhibits antioxidant activity by scavenging free radicals such as DPPH and superoxide anions. The compound also shows anti-inflammatory effects by reducing the production of pro-inflammatory cytokines and mediators. Its ability to inhibit pancreatic lipase has been confirmed in cell-free enzymatic assays. Additionally, the compound has demonstrated anticancer activity in various cancer cell lines, where it induces apoptosis and inhibits proliferation. The compound's effects are concentration-dependent, with effective concentrations typically ranging from 1 to 50 microM. |
| ln Vivo |
In vivo, Tetrahydroxymethoxychalcone has been studied in animal models for its anti-obesity and anti-inflammatory effects. In models of diet-induced obesity, administration of the compound reduces body weight gain, fat accumulation, and improves lipid profiles, likely due to pancreatic lipase inhibition and reduced fat absorption. The compound also demonstrates hepatoprotective effects in models of liver injury, reducing markers of liver damage and oxidative stress. Its anti-inflammatory activity translates to reduced edema and inflammatory cell infiltration in carrageenan-induced paw edema models. Despite its promise, detailed in vivo pharmacokinetic and efficacy studies are still emerging, and the compound has not yet advanced to clinical trials for any indication.
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| Enzyme Assay |
A standard non-cellular protocol for evaluating the antioxidant activity of Tetrahydroxymethoxychalcone involves the DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging assay. A 0.1 mM DPPH solution is prepared in methanol. Serial dilutions of the test compound (0.5-200 microg/mL) are prepared in methanol. For each concentration, 100 microL of DPPH solution is mixed with 100 microL of the sample solution in a 96-well plate and incubated in the dark for 30 minutes at room temperature. The absorbance is measured at 517 nm using a microplate reader. The percentage of DPPH radical scavenging is calculated as [(Acontrol - Asample)/Acontrol] × 100%. Ascorbic acid or Trolox is used as a positive control. The IC50 is calculated by plotting the percentage inhibition against the concentration. The compound typically shows dose-dependent DPPH scavenging activity.
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| Cell Assay |
An in vitro cellular protocol for evaluating the myogenic activity of Tetrahydroxymethoxychalcone uses murine C2C12 myoblasts. Cells are seeded in 6-well plates at a density of 5×10⁴ cells/well in DMEM supplemented with 10% FBS and 1% penicillin/streptomycin. For proliferation studies, cells are treated with various concentrations of the compound (0.5, 1, 5, 10, 25, 50 microM) for 24, 48, and 72 hours. Cell viability is assessed using an MTT assay. For differentiation studies, when cells reach 70-80% confluence, the medium is switched to DMEM with 2% horse serum and the compound for up to 7 days. Myotube formation is visualized by immunostaining with anti-Myosin Heavy Chain (MHC) antibody and DAPI for nuclei. The fusion index (percentage of nuclei within MHC-positive myotubes) is calculated to quantify differentiation. The compound should enhance both proliferation and differentiation compared to vehicle controls.
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| Animal Protocol |
An in vivo animal protocol for evaluating the anti-obesity activity of Tetrahydroxymethoxychalcone uses a high-fat diet-induced obesity (DIO) model. Male C57BL/6J mice (4-6 weeks old) are fed a high-fat diet (60% kcal from fat) for 8-12 weeks to induce obesity. Once obesity is established, mice are randomized into treatment groups (n=10 per group) and treated daily by oral gavage with Tetrahydroxymethoxychalcone (25, 50, or 100 mg/kg) or vehicle (0.5% methylcellulose) for 4-8 weeks. A positive control group receives orlistat (10 mg/kg). Body weight and food intake are monitored twice weekly. Fat mass is measured using an EchoMRI or by weighing dissected fat pads (subcutaneous, epididymal, and perirenal) at termination. Blood samples are collected for measurement of triglycerides, total cholesterol, LDL-cholesterol, HDL-cholesterol, and glucose. Liver and fat tissues are harvested for histological analysis (H&E staining) and gene expression analysis of lipid metabolism markers.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of Tetrahydroxymethoxychalcone have not been extensively characterized. As a natural polyphenolic compound, it is expected to have low oral bioavailability due to extensive first-pass metabolism, poor solubility, and efflux by transporters such as P-glycoprotein. In preclinical models, the compound may be detectable in plasma after oral administration, but at relatively low concentrations. It is likely metabolized by phase II enzymes (glucuronidation, sulfation) and possibly by gut microbiota. The compound may accumulate in tissues such as the liver and fat, which could contribute to its in vivo efficacy despite low systemic exposure. Further studies are needed to fully characterize its ADME properties.
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| Toxicity/Toxicokinetics |
Limited toxicity data are available for Tetrahydroxymethoxychalcone. As a naturally occurring polyphenolic compound present in licorice and other edible plants, it is generally considered safe at doses typically consumed in the diet. However, high doses or prolonged use may have potential toxicities that require further investigation. In acute toxicity studies in rodents, oral doses up to 1000 mg/kg did not cause mortality or significant adverse effects. The compound shows low cytotoxicity in normal cells at concentrations up to 50 microM, while selectively inhibiting cancer cell proliferation. Standard laboratory safety precautions should be followed when handling the compound, including the use of gloves and safety glasses. It is for research use only and should not be used in humans for therapeutic purposes without appropriate regulatory approval.
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| References | |
| Additional Infomation |
3,3',4,4'-Tetrahydroxy-2-methoxychalcone is a member of the chalcone family.
Tetrahydroxymethoxychalcone is a bioactive chalcone from licorice (Glycyrrhiza species) with potential applications in obesity, metabolic disorders, skin lightening, and muscle regeneration. Its chemical name is (E)-3-(3,4-dihydroxy-2-methoxyphenyl)-1-(3,4-dihydroxyphenyl)prop-2-en-1-one, with molecular formula C16H14O6 and molecular weight 302.28. Purity is typically ≥95%. The compound exhibits a range of beneficial activities, including pancreatic lipase inhibition (anti-obesity), tyrosinase inhibition (skin lightening), antioxidant activity, and promotion of myoblast differentiation (muscle regeneration). Despite its promise, Tetrahydroxymethoxychalcone has not received regulatory approval for clinical use and remains an investigational natural product. It is valuable for research into natural product-based therapies for obesity, metabolic diseases, and dermatological applications. |
| Molecular Formula |
C16H14O6
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|---|---|
| Molecular Weight |
302.28
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| Exact Mass |
302.079
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| CAS # |
197227-39-7
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| PubChem CID |
6478421
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| Appearance |
Light yellow to yellow solid
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
611.7±55.0 °C at 760 mmHg
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| Melting Point |
196 °C
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| Flash Point |
231.4±25.0 °C
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| Vapour Pressure |
0.0±1.8 mmHg at 25°C
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| Index of Refraction |
1.712
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| LogP |
2.05
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
22
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| Complexity |
409
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O(C)C1C(=C(C=CC=1/C=C/C(C1C=CC(=C(C=1)O)O)=O)O)O
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| InChi Key |
BICPGUILWBQAEY-GORDUTHDSA-N
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| InChi Code |
InChI=1S/C16H14O6/c1-22-16-9(3-7-13(19)15(16)21)2-5-11(17)10-4-6-12(18)14(20)8-10/h2-8,18-21H,1H3/b5-2+
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| Chemical Name |
(E)-3-(3,4-dihydroxy-2-methoxyphenyl)-1-(3,4-dihydroxyphenyl)prop-2-en-1-one
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| Synonyms |
Tetrahydroxymethoxychalcone
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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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
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| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.3082 mL | 16.5410 mL | 33.0819 mL | |
| 5 mM | 0.6616 mL | 3.3082 mL | 6.6164 mL | |
| 10 mM | 0.3308 mL | 1.6541 mL | 3.3082 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.
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