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| Targets |
2,4,6-Trihydroxybenzaldehyde is an orally active NF-kappaB inhibitor. It shows anti-tumor activity, anti-cancer cell proliferative activity, and anti-obesity activity.
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| ln Vitro |
In 3T3-L1 cells, 2,4,6-trihydroxybenzaldehyde prevents adipocyte development and lipid accumulation[1]. Down-regulating the expression levels of PPARγ, C/EBPα, SREBP-1c, and FAS protein is caused by 2,4,6-trihydroxybenzaldehyde[1].
In vitro, 2,4,6-Trihydroxybenzaldehyde exhibits anti-cancer cell proliferative activity and can inhibit NF-kappaB activation. It is used as a starting material for synthesizing potential protein glycation inhibitors and xanthine oxidase inhibitors. |
| ln Vivo |
2,4,6-Trihydroxybenzaldehyde (oral dosage; 5 and 25 mg/kg for 13 weeks) lowers serum levels of total cholesterol, triglycerides, and glucose and decreases the rise in weight gain caused by the HFD[1].
In vivo, 2,4,6-Trihydroxybenzaldehyde is an orally active NF-kappaB inhibitor with demonstrated anti-tumor activity in animal models. |
| Enzyme Assay |
Non-cell assays for NF-kappaB inhibition using this compound involve incubating it with purified NF-kappaB protein or using a cell-free transcription factor binding assay. Activity is measured by EMSA or by detecting the displacement of a labeled DNA probe from the NF-kappaB complex.
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| Cell Assay |
For cell studies, 2,4,6-Trihydroxybenzaldehyde is dissolved in DMSO and diluted in culture medium (final DMSO <0.1%). Cells (e.g., cancer cell lines) are treated for 24-72 hours. Cell viability is measured by MTT assay. NF-kappaB activation can be assessed by luciferase reporter assay.
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| Animal Protocol |
In animal studies, 2,4,6-Trihydroxybenzaldehyde is administered orally to rodents in models of cancer or obesity. Tumor growth and body weight are monitored, and tissue samples are collected for histology and analysis of NF-kappaB target gene expression.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
2,4,6-Trihydroxybenzaldehyde is a known human metabolite of anthocyanins. Limited PK data are available. The compound has phenolic hydroxyl groups and an aldehyde group, which may undergo phase II metabolism (glucuronidation, sulfation) and oxidation. It has moderate oral bioavailability. |
| Toxicity/Toxicokinetics |
The compound is generally considered safe at research doses. No significant toxicity has been reported in animal studies at therapeutic doses. Standard laboratory safety precautions apply.
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| References |
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| Additional Infomation |
2,4,6-Trihydroxybenzaldehyde is a carboxylic acid ester. It is functionally related to phloroglucinol.
2,4,6-Trihydroxybenzaldehyde is used as a research tool for NF-kappaB inhibition and as a starting material for the synthesis of biologically active molecules. It has potential therapeutic applications in cancer, obesity, and inflammatory diseases. It is not an approved drug. |
| Molecular Formula |
C7H6O4
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|---|---|
| Molecular Weight |
154.12
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| Exact Mass |
154.026
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| CAS # |
487-70-7
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| PubChem CID |
68099
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| Appearance |
Brown to orange solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
319.1±22.0 °C at 760 mmHg
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| Melting Point |
195 °C (dec.)(lit.)
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| Flash Point |
161.0±18.8 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.734
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| LogP |
1.37
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
11
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| Complexity |
135
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=C(C=C(C(=C1O)C=O)O)O
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| InChi Key |
BTQAJGSMXCDDAJ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H6O4/c8-3-5-6(10)1-4(9)2-7(5)11/h1-3,9-11H
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| Chemical Name |
2,4,6-trihydroxybenzaldehyde
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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: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| 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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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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.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.4885 mL | 32.4423 mL | 64.8845 mL | |
| 5 mM | 1.2977 mL | 6.4885 mL | 12.9769 mL | |
| 10 mM | 0.6488 mL | 3.2442 mL | 6.4885 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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