| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 10mg | |||
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| Targets |
Afzelechin targets multiple cellular pathways involved in inflammation and oxidative stress. It activates the Nrf2 (nuclear factor erythroid 2-related factor 2) pathway, increasing the binding activity between Nrf2 and antioxidant response elements (AREs). This leads to the upregulation of antioxidant and detoxification genes. Afzelechin also downregulates the TLR4/MyD88, NF-κB, and HMGB1/RAGE pathways, reducing the expression of pro-inflammatory cytokines such as IL-1β.
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| ln Vitro |
In vitro, afzelechin has demonstrated anti-inflammatory activity by reducing the production of pro-inflammatory cytokines in LPS-treated human umbilical vein endothelial cells (HUVECs). It activates the Nrf2/ARE pathway and downregulates TLR4/MyD88 and NF-κB signaling. The compound also exhibits antioxidant activity by reducing oxidative stress and apoptosis in cell-based models.
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| ln Vivo |
In vivo, afzelechin has shown protective effects in animal models. It alleviates deltamethrin-induced hepatic dysfunction by regulating the TLR4/My88, HMGB1/RAGE, and NF-κB pathways and reducing oxidative stress and apoptosis. It also mitigates sepsis-associated pulmonary injury. These findings suggest that afzelechin has potential as a hepatoprotective and anti-inflammatory agent.
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| Enzyme Assay |
Non-cellular assays for afzelechin involve assessing its antioxidant activity using cell-free systems. The compound's ability to scavenge free radicals can be evaluated using DPPH (2,2-diphenyl-1-picrylhydrazyl) or ABTS (2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)) radical scavenging assays. Its ability to inhibit lipid peroxidation can be measured using the thiobarbituric acid reactive substances (TBARS) assay.
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| Cell Assay |
In vitro cellular assays for afzelechin involve treating HUVECs or other cell lines with LPS to induce inflammation, followed by treatment with varying concentrations of afzelechin. The production of pro-inflammatory cytokines (e.g., IL-1β, TNF-α) is measured by ELISA. Nrf2 activation is assessed by measuring the expression of Nrf2 target genes (e.g., HO-1, NQO1) via qPCR. NF-κB activation is assessed by Western blotting for phosphorylated IκB or by measuring nuclear translocation of p65.
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| Animal Protocol |
In vivo animal experiments with afzelechin are conducted in rodent models of inflammation and organ injury. For example, in a deltamethrin-induced hepatic dysfunction model, mice are treated with afzelechin, and liver function is assessed by measuring serum markers (ALT, AST) and by histopathological examination of liver tissue. In a sepsis model, mice are subjected to cecal ligation and puncture (CLP) and treated with afzelechin to assess its protective effects against lung injury.
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| ADME/Pharmacokinetics |
Afzelechin has a molecular weight of 274.27 and a molecular formula of C₁₅H₁₄O₅. It is a solid powder with a purity of ≥98%. The compound is soluble in DMSO and is typically stored at -20°C, protected from light and moisture. Detailed pharmacokinetic parameters for afzelechin are not extensively characterized in general reference sources.
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| Toxicity/Toxicokinetics |
Afzelechin is a natural compound and is generally considered to have low toxicity. In preclinical studies, it has been well-tolerated at therapeutic doses. Standard laboratory safety precautions should be followed when handling the compound. It may cause skin, eye, and respiratory irritation. Appropriate personal protective equipment should be used.
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| References | |
| Additional Infomation |
Afzelechin is a tetrahydroxyflavanol with the structure (2S)-flavanol, substituted with hydroxyl groups at positions 3, 5, 7, and 4'. It is a plant metabolite and an EC 3.2.1.20 (α-glucosidase) inhibitor. It is a tetrahydroxyflavanol and catechin derived from the hydride of (2S)-flavanol. Afzelechin has been reported in peach (Prunus persica), wisteria (Wisteria floribunda), and other organisms with relevant data.
Afzelechin (CAS 2545-00-8) is a natural flavan-3-ol with antioxidant, anti-inflammatory, and hepatoprotective properties. It activates the Nrf2/ARE pathway and downregulates TLR4/MyD88, NF-κB, and HMGB1/RAGE signaling. It has shown protective effects in models of hepatic dysfunction and sepsis. Afzelechin is a valuable research tool for studying oxidative stress, inflammation, and related diseases. |
| Molecular Formula |
C15H14O5
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|---|---|
| Molecular Weight |
274.27
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| Exact Mass |
274.084
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| CAS # |
2545-00-8
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| PubChem CID |
442154
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| Appearance |
White to light brown solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
583.4±50.0 °C at 760 mmHg
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| Flash Point |
306.6±30.1 °C
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| Vapour Pressure |
0.0±1.7 mmHg at 25°C
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| Index of Refraction |
1.709
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| LogP |
1.09
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
20
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| Complexity |
328
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| Defined Atom Stereocenter Count |
2
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| SMILES |
C1[C@@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC=C(C=C3)O)O
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| InChi Key |
RSYUFYQTACJFML-DZGCQCFKSA-N
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| InChi Code |
InChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,13,15-19H,7H2/t13-,15+/m0/s1
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| Chemical Name |
(2R,3S)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
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| Synonyms |
NSC 135065 NSC-135065 Afzelechin
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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 Vitro) |
DMSO : ~100 mg/mL (~364.60 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.12 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 25.0 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: ≥ 2.5 mg/mL (9.12 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 25.0 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: ≥ 2.5 mg/mL (9.12 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.6460 mL | 18.2302 mL | 36.4604 mL | |
| 5 mM | 0.7292 mL | 3.6460 mL | 7.2921 mL | |
| 10 mM | 0.3646 mL | 1.8230 mL | 3.6460 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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