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| Other Sizes |
| Targets |
o-Vanillin targets fungal cell walls and membranes, compromising their integrity. It also targets hTLR2/1 and hTLR2/6 signaling pathways. In HEK293T cells, o-vanillin blocks hTLR2/1 and hTLR2/6 signaling with IC50 values of 24.2 μM and 37.2 μM in NF-κB reporter assays, respectively. It inhibits NF-κB activation induced by doxorubicin and 4-hydroperoxycyclophosphamide.
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| ln Vitro |
o-Vanillin (2-Vanillin; 0-125 μg/mL; 24-72 h) prevents A from growing mycelially. flavus in a way that is dependent on dose[1]. o-Vanillin (0-100 μg/mL; 48 h; A. flavus) alters mycelial shape and causes uneven mycelial shrinkage[1]. o-Vanillin (0-100 μg/mL; A. flavus) reduces the amount of β-1,3-glucan and protein on the surface of the cell wall[1]. o-Vanillin (0-100 μg/mL; A. flavus) degrades the integrity of cell membranes. o-Vanillin lowers the pH level outside of cells and releases components of cells[1]. o-Vanillin (0–100 μg/mL) could successfully stop A from growing. flavus on kernels of corn[1]. o-In A375/NFĸB-Luc cells, vanillin (0-250 μM) suppresses doxorubicin-mediated induction of NFĸB activity by 65%. o-Vanillin reduces the activity generated by 4-HC by 43%[2].
In vitro, o-vanillin inhibits the mycelial growth of fungi by disrupting cell wall and membrane integrity. It inhibits doxorubicin- and 4-hydroperoxycyclophosphamide-induced NF-κB activation. In HEK293T cells, it blocks hTLR2/1 and hTLR2/6 signaling with IC50 values of 24.2 μM and 37.2 μM, respectively. o-Vanillin also inhibits TLR2-mediated upregulation of MMP9, MMP14, IL-6, and iNOS expression. |
| ln Vivo |
In mice with A375 human melanoma xenografts, o-vanillin (2-Vanillin; 60 mg/kg; po; daily, for 5 d) suppresses tumor growth[2].
In vivo, o-vanillin inhibits TLR2/1-induced proinflammatory cytokines in mice. It blocks IL-12 p40 and TNF-α liver cytokine mRNA and serum protein. The compound has been shown to abrogate glioma supernatant-induced MMP9 and MMP14 expression in murine and human microglia. It is a valuable reagent for research applications in fungal pathogenesis and cancer studies. |
| Enzyme Assay |
For non-cellular assays, o-vanillin is evaluated for its antifungal activity using agar diffusion or broth microdilution methods. The compound is dissolved in appropriate solvents and tested against various fungal strains. Inhibition zones or MIC values are determined. For receptor binding studies, o-vanillin is tested in cell-free systems using purified TLR2 proteins or NF-κB reporter assays with purified components. Binding affinity to TLR2 can be assessed using SPR or ELISA-based methods.
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| Cell Assay |
In vitro cell culture experiments are performed using HEK293T cells for TLR2/1 and TLR2/6 signaling assays. Cells are treated with o-vanillin at concentrations ranging from 1 to 100 μM, and NF-κB activation is measured using luciferase reporter assays. For antifungal activity, fungal cultures are treated with o-vanillin at various concentrations, and mycelial growth is measured. Cytotoxicity is assessed using standard cell viability assays in mammalian cell lines.
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| Animal Protocol |
Animal/Disease Models: Male NSG mice with A375 human melanoma xenografts (12-16 weeks of age)[2]
Doses: 60 mg/kg Route of Administration: Oral administration; daily, for 5 days Experimental Results: Delayed the growth of A375 human melanoma xenografts in immunodeficient NSG mice. In vivo animal studies are conducted in mouse models. o-Vanillin is administered orally or intraperitoneally. In TLR2/1-induced inflammation models, mice are treated with o-vanillin, and proinflammatory cytokine levels (IL-12 p40, TNF-α) are measured in serum and liver tissue. Glioma models are used to study the effect of o-vanillin on MMP9 and MMP14 expression in microglia. Endpoints include cytokine quantification, histological analysis, and behavioral assessments. |
| ADME/Pharmacokinetics |
o-Vanillin has a molecular formula of C8H8O3 and a molecular weight of 152.15 g/mol. It is a benzaldehyde class aromatic aldehyde. The compound is a natural product that can be isolated from Pinus koraiensis fruit. It is soluble in organic solvents and has moderate aqueous solubility. Pharmacokinetic properties are not well characterized, but the compound is used primarily in research settings for its antifungal and anti-inflammatory activities.
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| Toxicity/Toxicokinetics |
o-Vanillin is considered relatively safe for research use at standard laboratory concentrations. It is classified as an irritant and requires appropriate safety precautions during handling. In vitro cytotoxicity has been evaluated in various cell lines, and the compound shows moderate toxicity at high concentrations. In vivo toxicity data are limited, but the compound has been used in animal studies without significant adverse effects at effective doses.
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| References |
[1]. Li Q, et, al. o-Vanillin, a promising antifungal agent, inhibits Aspergillus flavus by disrupting the integrity of cell walls and cell membranes. Appl Microbiol Biotechnol. 2021 Jun;105(12):5147-5158.
[2]. Marton A, et, al. Vanillin Analogues o-Vanillin and 2,4,6-Trihydroxybenzaldehyde Inhibit NFĸB Activation and Suppress Growth of A375 Human Melanoma. Anticancer Res. 2016 Nov;36(11):5743-5750. |
| Additional Infomation |
o-Vanillin is a benzaldehyde compound, a salicylaldehyde compound in which a methoxy group is substituted at the 3-position. It possesses antimutagenic and plant metabolite-like properties. o-Vanillin belongs to the benzaldehyde and guaiacol groups, and its function is related to that of salicylaldehyde. 2-Hydroxy-3-methoxybenzaldehyde has been reported in Strychnos cathayensis, Hyssopus officinalis, and Panax ginseng, and relevant data are available.
o-Vanillin is also known as 2-Vanillin and 3-Methoxysalicylaldehyde. It is a potent antifungal agent that inhibits mycelial growth by disrupting cell walls and membranes. It also inhibits NF-κB activation and TLR2-mediated signaling. The compound is used in research on fungal pathogenesis, cancer, and inflammation. It is for research use only and is not intended for therapeutic applications. |
| Molecular Formula |
C8H8O3
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|---|---|
| Molecular Weight |
152.15
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| Exact Mass |
152.047
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| CAS # |
148-53-8
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| PubChem CID |
8991
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
265.5±0.0 °C at 760 mmHg
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| Melting Point |
40-42 °C(lit.)
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| Flash Point |
94.0±15.3 °C
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| Vapour Pressure |
0.0±0.5 mmHg at 25°C
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| Index of Refraction |
1.588
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| LogP |
1.4
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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])C1=C([H])C([H])=C([H])C(C([H])=O)=C1O[H]
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| InChi Key |
JJVNINGBHGBWJH-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H8O3/c1-11-7-4-2-3-6(5-9)8(7)10/h2-5,10H,1H3
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| Chemical Name |
2-hydroxy-3-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: 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) |
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 | 6.5725 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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