| Size | Price | Stock | Qty |
|---|---|---|---|
| 100mg |
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| Other Sizes |
| ADME/Pharmacokinetics |
Metabolism / Metabolites
Flavonoids have been reported to be effective against the toxicity of peroxynitrite. Two pharmacophores have been identified in flavonoids: a catechol group on the B ring and a hydroxyl group (OH) at the 3-position. This study further explored this structure-activity relationship. The study found that catechol (1,2-dihydroxybenzene) is an effective peroxynitrite scavenger, while phenol (hydroxybenzene) does not possess this ability. Among flavonols lacking a catechol group on the B ring, kaempferol (with OH groups at positions 3, 5, 7, and 4') and galangin (with OH groups at positions 3, 5, and 7) are also effective scavengers, while apigenin (with OH groups at positions 5, 7, and 4') and apigenin (with OH groups at positions 5 and 7) do not. This confirms the importance of the hydroxyl group at position 3. However, the synthesized flavonol TUM 9761 and 3-hydroxyflavone (with a hydroxyl group only at position 3) exhibited poor scavenging activity. Based on these results, we further refined the structure-activity relationship of the flavonol's activity in scavenging peroxynitrite. The catechol group on ring B remains important. The 3-hydroxyl group also remains important, but the activity of this pharmacophore is affected by the substituents at positions 5 and 7. Known metabolites of 3-hydroxyflavonoids include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-(4-oxo-2-phenylchromen-3-yl)oxaoxane-2-carboxylic acid. |
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| Toxicity/Toxicokinetics |
Interactions
Male Fischer 344 rats were fed a diet supplemented with 0.1% (w/w) 3-hydroxyflavone… After 2 weeks, they were treated twice with azomethane (AOM) (15 mg/kg, subcutaneously) (1 week apart); the diet treatment continued until sacrifice, i.e., 7 weeks after the first AOM injection. …3-hydroxyflavone slightly but significantly increased the number of abnormal crypt foci (ACF) per colon (P < 0.05) (157 ± 7 in the control group and 198 ± 14 in the 3-hydroxyflavone group, n = 10). … The inhibitory effect of flavonoids on LOOH-induced cytotoxicity of rat pheochromocytoma PC12 cells was investigated. The degree of cytotoxicity was expressed as the percentage of survival determined by trypan blue exclusion. Pre-incubation of cells with 3-hydroxyflavone, quercetin, or luteolin before LOOH exposure significantly inhibited cytotoxicity. Conversely, cytotoxicity was significantly reduced when cells were co-incubated with senna, quercetin, kaempferol, luteolin, or 3-hydroxyflavone and LOOH. Therefore, regardless of incubation conditions, quercetin, 3-hydroxyflavone, and luteolin were superior to other flavonoids as protective agents against cytotoxicity. Furthermore, these flavonoids exhibited inhibitory effects under co-incubation conditions rather than pre-incubation conditions. ... Non-human toxicity values Mice intravenous LD50: 56 mg/kg |
| Additional Infomation |
Flavonols are monohydroxy flavones, specifically 3-hydroxy derivatives of flavones. They belong to the flavonol class of compounds. They are the conjugate acid of flavonol (1-). 3-Hydroxyflavones have been reported in tea (Camellia sinensis), hops (Humulus lupulus), and other organisms with relevant data. See also: Flavonoids (note moved to). Mechanism of Action: Epidermal growth factor (EGF) has been shown to induce cell proliferation; however, the role of prostaglandin E2 (PGE2) in EGF-induced cell proliferation remains unclear. MTT and [3H]thymidine incorporation experiments showed that both EGF and PGE2 promoted the proliferation of epidermal-like cancer cells A431. Among the nine structure-related compounds, the natural product 3-hydroxyflavone exhibited the strongest inhibitory activity against EGF-induced cell proliferation. Furthermore, 3-hydroxyflavone inhibited EGF receptor phosphorylation, ERK1/2 phosphorylation, and the production of COX-2/PGE₂. MTT and soft agar colony formation assays showed that the addition of PGE₂ attenuated the inhibitory effect of 3-hydroxyflavone on EGF-induced cell proliferation. In addition, the inhibitory effect of 3-hydroxyflavone on EGF-induced cell proliferation in A431 cells was more specific than its inhibitory effect on fetal bovine serum (FBS)-induced cell proliferation. These results indicate that PGE₂ is an important downstream molecule in EGF-induced cell proliferation, and 3-hydroxyflavone inhibits PGE₂ production by blocking the MAPK signaling pathway, thus potentially possessing the potential for developing anticancer drugs.
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| Molecular Formula |
C15H10O3
|
|---|---|
| Molecular Weight |
238.24
|
| Exact Mass |
238.063
|
| CAS # |
577-85-5
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| PubChem CID |
11349
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.367 g/cm3
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| Boiling Point |
393.7ºC at 760 mmHg
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| Melting Point |
171-172 °C(lit.)
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| Flash Point |
151.5ºC
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| Index of Refraction |
1.679
|
| LogP |
3.165
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| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
18
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| Complexity |
366
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
HVQAJTFOCKOKIN-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C15H10O3/c16-13-11-8-4-5-9-12(11)18-15(14(13)17)10-6-2-1-3-7-10/h1-9,17H
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| Chemical Name |
3-hydroxy-2-phenylchromen-4-one
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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: 33.33 mg/mL (139.90 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (10.49 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
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 (10.49 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. 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 (10.49 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 | 4.1974 mL | 20.9872 mL | 41.9745 mL | |
| 5 mM | 0.8395 mL | 4.1974 mL | 8.3949 mL | |
| 10 mM | 0.4197 mL | 2.0987 mL | 4.1974 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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