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| Targets |
(-)-Butin targets the PI3K/Akt signaling pathway, which activates Nrf2-mediated MnSOD induction. As a flavonoid, it exhibits antioxidant activity by scavenging free radicals and protecting against oxidative stress. The compound has antiplatelet activity, preventing platelet aggregation. Its anti-inflammatory activity involves modulation of inflammatory pathways. The compound's multiple targets make it valuable for cardiovascular and oxidative stress research.
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| ln Vitro |
(-)-Butin protects cells against H2O2-induced apoptosis, oxidative DNA damage, and oxidative mitochondrial dysfunction in vitro. The compound attenuates oxidative stress by activating Nrf2-mediated MnSOD induction via the PI3K/Akt signaling pathway. It exhibits strong antioxidant, antiplatelet, and anti-inflammatory activities. These in vitro findings support its potential applications in cardiovascular research, oxidative stress research, and anti-inflammatory research.
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| ln Vivo |
In vivo studies of (-)-Butin are limited as the compound is primarily used as a research chemical. Its strong antioxidant, antiplatelet, and anti-inflammatory activities suggest potential for in vivo evaluation in models of cardiovascular disease, oxidative stress, and inflammation. However, comprehensive in vivo pharmacological studies specifically targeting (-)-Butin are not well documented. The compound is intended for research use only and is not for human therapeutic use.
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| Enzyme Assay |
In vitro antioxidant assays for (-)-Butin typically involve testing its ability to protect cells against H2O2-induced oxidative damage. Cells are treated with varying concentrations of the compound and exposed to H2O2; cell viability, DNA damage, and mitochondrial function are assessed. Nrf2 activation is measured by assessing MnSOD induction via the PI3K/Akt pathway. Antiplatelet activity is assessed using platelet aggregation assays. The compound's purity and identity are confirmed using analytical chemistry methods.
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| Cell Assay |
In vitro cell-based assays for (-)-Butin involve culturing cells to evaluate its antioxidant and cytoprotective effects. Cells are treated with varying concentrations of the compound and exposed to H2O2 to induce oxidative stress. Cell viability is assessed using MTT or similar colorimetric assays. Oxidative DNA damage is assessed using comet assays. Mitochondrial dysfunction is assessed by measuring mitochondrial membrane potential. Nrf2 activation and MnSOD induction are measured by Western blotting. All experiments are performed with appropriate controls.
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| Animal Protocol |
In vivo animal experiments for (-)-Butin would be conducted to evaluate its antioxidant, antiplatelet, and anti-inflammatory activities. For antioxidant studies, animals would be administered the compound and markers of oxidative stress measured. For antiplatelet studies, platelet aggregation would be assessed ex vivo. For anti-inflammatory studies, animals with induced inflammation would be treated and inflammatory markers measured. Parameters assessed would include oxidative stress markers, platelet aggregation, and tissue histopathology. Control groups receiving vehicle alone would be included for comparison.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of (-)-Butin reflect its nature as a flavonoid. It has a molecular weight of 272.25 and the molecular formula C15H12O5. As a flavonoid, it would be absorbed through the gastrointestinal tract and metabolized through standard xenobiotic pathways in the liver. Complete pharmacokinetic profiling including half-life, clearance, volume of distribution, and bioavailability would require further systematic studies using appropriate analytical methods such as high-performance liquid chromatography-mass spectrometry.
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| Toxicity/Toxicokinetics |
The toxicity profile of (-)-Butin has been evaluated in the context of its use as a research chemical. As a naturally occurring flavonoid from Dalbergia odorifera, it is expected to have a favorable safety profile at research concentrations. Proper handling procedures including use of personal protective equipment are recommended when working with pure compound. The compound is not approved for human therapeutic use and is intended for research purposes only. Long-term toxicity studies would be needed to fully establish its safety profile.
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| References |
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| Additional Infomation |
Butin is a trihydroxyflavanone with its three hydroxyl substituents located at the 3', 4', and 7 positions. It is found in black locust (Acacia mearnsii), worm-resistant aster (Vernonia anthelmintica), and rosewood (Dalbergia odorifera), and has a protective effect against oxidative stress-induced mitochondrial dysfunction. It possesses antioxidant, protective, and metabolic functions. Butin is a trihydroxyflavanone, belonging to the 4'-hydroxyflavanone class of compounds. Butin has also been reported to be found in Spatholobus suberectus, Bolusanthus speciosus, and other organisms with relevant data.
(-)-Butin (CAS# 492-14-8) is the S enantiomer of Butin, a major biologically active flavonoid isolated from the heartwood of Dalbergia odorifera. It has the molecular formula C15H12O5 and a molecular weight of 272.25. (-)-Butin exhibits strong antioxidant, antiplatelet, and anti-inflammatory activities. It protects cells against H2O2-induced apoptosis and oxidative damage by activating Nrf2-mediated MnSOD induction via the PI3K/Akt signaling pathway. |
| Molecular Formula |
C15H12O5
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| Molecular Weight |
272.25
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| Exact Mass |
272.068
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| CAS # |
492-14-8
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| Related CAS # |
(+)-Butin; 74628-42-5; Butin; 21913-99-5
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| PubChem CID |
92775
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| Appearance |
Yellow to brown solid
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| Density |
1.485
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| Boiling Point |
582.4±50.0 °C at 760 mmHg
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| Melting Point |
224-226ºC
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| Flash Point |
226.7±23.6 °C
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| Vapour Pressure |
0.0±1.7 mmHg at 25°C
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| Index of Refraction |
1.693
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| LogP |
2.16
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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 |
1
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| Heavy Atom Count |
20
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| Complexity |
371
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| Defined Atom Stereocenter Count |
1
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| SMILES |
OC1C=CC([C@H]2CC(=O)C3C=CC(=CC=3O2)O)=CC=1O
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| InChi Key |
MJBPUQUGJNAPAZ-AWEZNQCLSA-N
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| InChi Code |
InChI=1S/C15H12O5/c16-9-2-3-10-12(18)7-14(20-15(10)6-9)8-1-4-11(17)13(19)5-8/h1-6,14,16-17,19H,7H2/t14-/m0/s1
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| Chemical Name |
(2S)-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydrochromen-4-one
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| Synonyms |
(-)-Butin
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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 |
| 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: 190 mg/mL (697.89 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 4.75 mg/mL (17.45 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 47.5 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: ≥ 4.75 mg/mL (17.45 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 47.5 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: ≥ 4.75 mg/mL (17.45 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 | 3.6731 mL | 18.3655 mL | 36.7309 mL | |
| 5 mM | 0.7346 mL | 3.6731 mL | 7.3462 mL | |
| 10 mM | 0.3673 mL | 1.8365 mL | 3.6731 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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