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| Targets |
3-Formylphenylboronic acid functions as a biological inhibitor of γ-glutamyltranspeptidase (GGT), an enzyme that plays a key role in glutathione metabolism and the gamma-glutamyl cycle. By inhibiting GGT, the compound may affect cellular redox homeostasis and glutathione levels. The compound also binds to the chelate ligand of a macrocyclic structure. The binding mechanism of phenylboronic acid moieties, including 3-formylphenylboronic acid, involves a reversible covalent interaction with diol-containing molecules, such as sugars and glycoproteins. This interaction is the basis for its applications in glucose sensing and insulin delivery. The compound has been shown to have hypoglycemic effects in rats and binding constants for proteins ranging from 10 μM to 1 mM. It also exhibits affinity for various receptors, making it a valuable tool for studying receptor-ligand interactions. In the context of Suzuki-Miyaura reactions, the compound interacts with palladium catalysts to facilitate transmetalation and carbon-carbon bond formation.
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| ln Vitro |
In vitro, 3-formylphenylboronic acid is used as a reagent in palladium-catalyzed homocoupling and Suzuki coupling reactions. It is also used to study the effects of boronic acid on fluoride-selective chemosignaling behavior of merocyanine dye and as exciton-coupled CD probes for epigallocatechin gallate. The compound has demonstrated antimicrobial properties, with studies indicating moderate action against fungal species like Candida albicans and higher activity against bacteria such as Escherichia coli and Bacillus cereus. The compound's derivatives have been explored for potential in glucose sensing, insulin delivery, and antimicrobial applications. Its formyl group provides additional reactivity for further functionalization, enabling the synthesis of various derivatives with enhanced biological activity. In organic synthesis, it serves as a versatile building block for constructing complex molecular architectures.
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| ln Vivo |
In vivo, 3-formylphenylboronic acid has been shown to have hypoglycemic effects in rats. This suggests that the compound or its derivatives may have potential applications in the treatment of diabetes and metabolic disorders. The compound's ability to bind to proteins and other biomolecules in vivo may underlie its observed biological effects. Binding constants for proteins ranging from 10 μM to 1 mM have been reported, indicating moderate to weak interactions with biological targets. The compound's antimicrobial properties have been explored in vivo, with studies indicating potential efficacy against bacterial and fungal infections. However, comprehensive in vivo studies are limited, and further research is needed to fully characterize the compound's pharmacological profile. The compound's potential in glucose sensing and insulin delivery suggests possible applications in diabetes management, but these are primarily in the research stage.
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| Enzyme Assay |
Cell-free assays involving 3-formylphenylboronic acid include standard Suzuki-Miyaura coupling protocols: the compound (1.2 equivalents) is mixed with an aryl halide, a palladium catalyst (2-5 mol%), a base (e.g., K2CO3), and a solvent such as toluene or water at 80-100°C for 12-24 hours. The reaction progress is monitored by TLC or HPLC, and the product is purified by column chromatography. For studying γ-glutamyltranspeptidase inhibition, the compound is incubated with the enzyme and a suitable substrate in buffer, and the enzymatic activity is measured spectrophotometrically. For studying fluoride-selective chemosignaling, the compound is used as a probe in merocyanine dye systems. For exciton-coupled CD probes, the compound is used to study epigallocatechin gallate interactions. The compound's binding to proteins can be studied using various biophysical techniques, including fluorescence spectroscopy and surface plasmon resonance.
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| Cell Assay |
Cellular assays with 3-formylphenylboronic acid are not standard, as the compound is primarily a chemical reagent. However, its antimicrobial activity has been evaluated in microbiological assays against bacterial and fungal cultures. In these assays, the compound or its derivatives are incubated with microbial cultures, and growth inhibition is measured using standard methods such as broth microdilution to determine minimum inhibitory concentrations. The compound's derivatives have shown moderate action against Candida albicans and higher activity against Escherichia coli and Bacillus cereus. For studying the compound's effects on glucose sensing or insulin delivery, cell-based assays may involve measuring glucose uptake or insulin secretion in relevant cell lines. However, these applications are primarily in the research stage and not yet widely adopted in standard cellular assays.
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| Animal Protocol |
Animal studies with 3-formylphenylboronic acid have demonstrated hypoglycemic effects in rats. In these studies, the compound is typically administered orally or intraperitoneally, and blood glucose levels are measured over time to assess its glucose-lowering effects. The compound's binding constants for proteins ranging from 10 μM to 1 mM suggest that it may interact with various proteins in vivo. The compound's potential in insulin delivery and glucose sensing has been explored in animal models of diabetes. Antimicrobial activity has also been evaluated in animal models of infection. However, comprehensive in vivo studies are limited, and further research is needed to fully characterize the compound's pharmacological and toxicological profile in animals.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for 3-formylphenylboronic acid are not well characterized. As a boronic acid with a formyl group (molecular weight 149.94 g/mol), it may undergo rapid clearance and metabolism in biological systems. The compound's ability to bind to proteins and other biomolecules may influence its distribution and elimination. The formyl group adds reactivity for further functionalization, which may affect the compound's pharmacokinetic properties. The compound has been shown to have hypoglycemic effects in rats, suggesting that it is absorbed and reaches systemic circulation. However, comprehensive pharmacokinetic studies, including absorption, distribution, metabolism, and excretion, have not been performed. The compound is not intended for therapeutic use, and pharmacokinetic profiling is primarily conducted for research purposes.
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| Toxicity/Toxicokinetics |
Toxicological data indicate that 3-formylphenylboronic acid is classified as Skin Corr. 1B (skin corrosive). This indicates that the compound can cause severe skin burns and eye damage upon contact. Appropriate personal protective equipment, including eyeshields, faceshields, gloves, and type P3 (EN 143) respirator cartridges, are required when handling the compound. The compound should be handled in a well-ventilated area, and contact with skin and eyes should be avoided. In case of exposure, affected areas should be rinsed thoroughly with water, and medical attention should be sought if necessary. The compound is classified with a storage class of 8A (combustible corrosive hazardous materials) and a WGK (water hazard class) of 3. Comprehensive toxicological evaluation, including carcinogenicity and mutagenicity studies, has not been performed. As with all research chemicals, it should be handled with care and used only in accordance with safety guidelines.
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| Additional Infomation |
3-Formylphenylboronic acid is a research chemical, not an approved drug. It has no clinical trial or marketing approval status for therapeutic use. The compound is used as a reagent in palladium-catalyzed homocoupling and Suzuki coupling reactions. It serves as a biological inhibitor of γ-glutamyltranspeptidase and is used to study the effects of boronic acid on fluoride-selective chemosignaling behavior of merocyanine dye and as exciton-coupled CD probes for epigallocatechin gallate. The compound's derivatives have been explored for potential in glucose sensing, insulin delivery, and antimicrobial applications. It has demonstrated hypoglycemic effects in rats and antimicrobial properties against various pathogens. The compound contains varying amounts of anhydride and is classified as Skin Corr. 1B. It should be stored in a cool, dry place away from incompatible materials.
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| Molecular Formula |
C7H7BO3
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| Molecular Weight |
149.94
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| Exact Mass |
150.048
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| CAS # |
87199-16-4
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| PubChem CID |
2734356
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| Appearance |
Off-white to light yellow solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
354.4±44.0 °C at 760 mmHg
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| Melting Point |
182-186 °C
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| Flash Point |
168.1±28.4 °C
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| Vapour Pressure |
0.0±0.8 mmHg at 25°C
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| Index of Refraction |
1.548
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| LogP |
1.01
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
11
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| Complexity |
138
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=CC1C=C(B(O)O)C=CC=1
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| InChi Key |
HJBGZJMKTOMQRR-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H7BO3/c9-5-6-2-1-3-7(4-6)8(10)11/h1-5,10-11H
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| Chemical Name |
(3-formylphenyl)boronic acid
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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 | 6.6693 mL | 33.3467 mL | 66.6933 mL | |
| 5 mM | 1.3339 mL | 6.6693 mL | 13.3387 mL | |
| 10 mM | 0.6669 mL | 3.3347 mL | 6.6693 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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