| Size | Price | Stock | Qty |
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| 5g |
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| 10g |
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| 25g |
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| Other Sizes |
| Targets |
Aldehyde oxidase
Isovanillin primarily targets aldehyde oxidase (AO), acting as a selective inhibitor of this enzyme. It is not a substrate for aldehyde oxidase, distinguishing it from other aldehydes. The compound also exhibits activity against HIV protease. Its antispasmodic effects are mediated through relaxation of ileum contractions induced by 5-HT. As a plant metabolite, it may interact with various biological pathways in different organisms. |
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| ln Vitro |
Aldehyde dehydrogenase is primarily responsible for the metabolism of isovanillin to isovillic acid because it is not a substrate of aldehyde oxidase [1]. 5-HT-induced ileal contractions can be relaxed by isovanillin (IC50=356±50μM) [2].
In vitro, Isovanillin inhibits aldehyde oxidase activity. It is not a substrate for aldehyde oxidase and is metabolized to isovanillic acid predominantly by aldehyde dehydrogenase. The compound relaxes 5-HT-induced ileal contractions with an IC50 of 356 ± 50 μM. It exhibits antispasmodic and antidiarrheal activities in various assay systems. Its antifungal and HIV protease inhibitory activities have also been characterized in vitro. |
| ln Vivo |
On the gastrointestinal tract, isoacetyl vanillin (2 mg/kg, 5 mg/kg) and isovanillin (2 mg/kg, 5 mg/kg) both have antiperistaltic and antidiarrheal properties [3].
In vivo, Isovanillin demonstrates antiperistaltic and antidiarrheal properties on the gastrointestinal tract. At doses of 2 mg/kg and 5 mg/kg, both isoacetyl vanillin and isovanillin exhibit these effects. The compound's metabolism to isovanillic acid by aldehyde dehydrogenase occurs in vivo. Its antispasmodic and antidiarrheal activities suggest potential for gastrointestinal research applications. |
| Enzyme Assay |
In vitro enzyme assays for Isovanillin involve measuring aldehyde oxidase inhibition. Enzyme activity is assessed using suitable substrates, and the compound is added at varying concentrations to determine inhibition. As Isovanillin is not a substrate for aldehyde oxidase, its metabolism is studied using aldehyde dehydrogenase assays to monitor the conversion to isovanillic acid. For antispasmodic activity, ileum contractions induced by 5-HT are measured in organ bath studies, with IC50 values calculated from dose-response curves.
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| Cell Assay |
In vitro cell-based assays for Isovanillin are conducted in various cell lines to assess its antifungal and antiviral activities. Cells are cultured in appropriate media at 37°C with 5% CO2 and treated with the compound at varying concentrations. Antifungal activity is assessed by measuring fungal growth inhibition. HIV protease inhibitory activity is evaluated using enzymatic assays. Cell viability is assessed by standard assays such as MTT. Experiments are performed in triplicate with appropriate positive and negative controls.
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| Animal Protocol |
In vivo animal studies for Isovanillin are conducted in rodent models to assess its gastrointestinal effects. Animals are treated with Isovanillin via oral administration at doses of 2 mg/kg and 5 mg/kg. Antidiarrheal and antiperistaltic activities are evaluated by measuring gastrointestinal transit and fecal output. The compound's metabolism to isovanillic acid is assessed by analyzing blood and tissue samples. Animals are monitored for clinical signs. Studies are conducted in accordance with institutional animal care guidelines.
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| ADME/Pharmacokinetics |
Isovanillin (MW 152.15 g/mol, C8H8O3) has a density of 1.2±0.1 g/cm³, a boiling point of 308.1±0.0 °C at 760 mmHg, and a melting point of 113-116 °C. It is soluble in organic solvents. LogP is 1.1. The compound is metabolized by aldehyde dehydrogenase to isovanillic acid. It is stable as a powder at -20°C for 3 years and at 4°C for 2 years; in solvent at -80°C for 6 months and at -20°C for 1 month. Requires protection from light and moisture.
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| Toxicity/Toxicokinetics |
Isovanillin is generally well-tolerated in preclinical studies. It is an aldehyde oxidase inhibitor with antispasmodic, antidiarrheal, antifungal, and HIV protease inhibitory activities. No significant adverse effects have been reported in the available literature at research-use concentrations. The compound is intended for research use only. Standard safety precautions should be followed when handling. Comprehensive toxicological evaluation would be required for therapeutic development.
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| References |
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| Additional Infomation |
Isovalin belongs to the benzaldehyde class of compounds and is a compound in which 4-methoxybenzaldehyde is substituted with a hydroxyl group at the 3-position. It is an aldehyde oxidase inhibitor. Isovalin has multiple functions, including as an EC 1.2.3.1 (aldehyde oxidase) inhibitor, a plant metabolite, an antidiarrheal agent, an antifungal agent, an HIV protease inhibitor, and an animal metabolite. It belongs to the phenolic, monomethoxybenzene, and benzaldehyde classes of compounds. Isovalin has been reported to exist in Bowdichia virgilioides, Ficus erecta var. beecheyana, and other organisms with relevant data.
Isovanillin (3-hydroxy-4-methoxybenzaldehyde) is a phenolic aldehyde and positional isomer of vanillin that selectively inhibits aldehyde oxidase. It is not a substrate for aldehyde oxidase and is metabolized by aldehyde dehydrogenase to isovanillic acid. The compound exhibits antispasmodic (IC50 = 356 ± 50 μM for 5-HT-induced ileal contractions), antidiarrheal, antifungal, and HIV protease inhibitory activities. It is a plant and animal metabolite found in various organisms. All applications are limited to non-human research use. |
| Molecular Formula |
C8H8O3
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|---|---|
| Molecular Weight |
152.1473
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| Exact Mass |
152.047
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| CAS # |
621-59-0
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| Related CAS # |
Isovanillin-d3; 74495-73-1
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| PubChem CID |
12127
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| Appearance |
White to off-white solid
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
308.1±0.0 °C at 760 mmHg
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| Melting Point |
113-116 °C
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| Flash Point |
119.9±15.3 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.588
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| LogP |
1.1
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| Hydrogen Bond Donor Count |
1
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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 |
135
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O(C([H])([H])[H])C1C([H])=C([H])C(C([H])=O)=C([H])C=1O[H]
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| InChi Key |
JVTZFYYHCGSXJV-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H8O3/c1-11-8-3-2-6(5-9)4-7(8)10/h2-5,10H,1H3
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| Chemical Name |
3-hydroxy-4-methoxybenzaldehyde
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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: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). 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) |
DMSO : ~100 mg/mL (~657.25 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.43 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 (16.43 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 (16.43 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 | 6.5725 mL | 32.8623 mL | 65.7246 mL | |
| 5 mM | 1.3145 mL | 6.5725 mL | 13.1449 mL | |
| 10 mM | 0.6572 mL | 3.2862 mL | 6.5725 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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