| Size | Price | Stock | Qty |
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| 100mg |
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| Other Sizes |
| Targets |
O-allylvanillin is an O-allylchalcone derivative with anti-cancer effects. As a chalcone analogue, it may target multiple cellular pathways involved in cancer cell proliferation, apoptosis, and inflammation. The specific molecular targets are not fully defined, but it is likely to interact with tubulin (inhibiting polymerization), modulate NF-kappaB signaling, and induce apoptosis through the intrinsic (mitochondrial) pathway. The allyl group enhances its reactivity and biological activity compared to vanillin.
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| ln Vitro |
In vitro, O-allylvanillin inhibits the growth of several human cancer cell lines. It suppresses the growth of THP-1 (human acute monocytic leukemia) cells with an IC50 of 74.76 microM, HL60 (human acute promyelocytic leukemia) cells with an IC50 of 63.52 microM, Hep-G2 (human liver cancer) cells with an IC50 of 90.99 microM, and MCF-7 (human breast cancer) cells with an IC50 of 90.11 microM. This anti-cancer activity is attributed to its ability to induce apoptosis, arrest the cell cycle, and inhibit cell proliferation. It is also used in organic synthesis, fragrance development, and as a bioactive compound intermediate.
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| ln Vivo |
In vivo, O-allylvanillin has been reported to have anti-neoplastic (anti-cancer) activities in preclinical models. Its mechanism of action is thought to involve the suppression of tumor growth, possibly through the induction of apoptosis and inhibition of angiogenesis. Detailed in vivo efficacy data from animal models is not provided in standard literature. As a chalcone derivative, it would typically be tested in a mouse xenograft model of a sensitive cancer cell line (e.g., HL60 or MCF-7) to assess tumor growth inhibition. The compound is a synthetic derivative of vanillin and is used in pharmacological research for its anti-cancer properties.
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| Enzyme Assay |
There is no standard cell-free assay specific to O-allylvanillin. A generic biochemical assay for anti-cancer agents is a tubulin polymerization assay. Purified tubulin (from bovine brain) is incubated with varying concentrations of O-allylvanillin (0-500 microM) and GTP in a 96-well plate. The reaction is monitored at 340 nm (turbidity) to measure the rate of tubulin polymerization into microtubules. The half-maximal inhibitory concentration (IC50) for inhibiting tubulin polymerization can be calculated. This assay helps determine if the compound's anti-cancer activity is mediated through microtubule disruption.
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| Cell Assay |
A standard in vitro cellular assay for O-allylvanillin is a cytotoxicity assay using human cancer cell lines such as THP-1, HL60, Hep-G2, and MCF-7. Cells are seeded in 96-well plates at a density of 5 × 103 to 1 × 10⁴ cells/well and treated with varying concentrations of O-allylvanillin (e.g., 0-200 microM) for 48-72 hours. Cell viability is measured by MTT, CCK-8, or CellTiter-Glo assay. The half-maximal inhibitory concentration (IC50) is calculated from the dose-response curve. Apoptosis can be confirmed by Annexin V-FITC/PI staining and flow cytometry. Cell cycle distribution can be analyzed by propidium iodide (PI) staining and flow cytometry.
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| Animal Protocol |
To assess the in vivo efficacy of O-allylvanillin, a mouse xenograft model can be used. Immunodeficient mice (e.g., BALB/c nude mice) are subcutaneously implanted with human cancer cells, such as MCF-7 (breast cancer) or HL60 (leukemia) cells (5 × 10⁶ cells/mouse, mixed 1:1 with Matrigel). When tumors reach approximately 100 mm3, mice are randomized into vehicle control and O-allylvanillin treatment groups. The compound is administered at doses of 10-100 mg/kg via intraperitoneal (IP) injection or oral gavage, daily or every other day for 14-21 days. Tumor volume (length×width2/2) and body weight are measured every 2-3 days. At the end of the study, tumors are collected for histopathological analysis (H&E, Ki-67 immunostaining, TUNEL assay).
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| ADME/Pharmacokinetics |
O-allylvanillin has a molecular weight of 192.21 and a molecular formula of C11H12O3. It is a lipophilic compound with a predicted LogP around 2-2.5. It is soluble in organic solvents such as ethanol, DMSO, and DMF. For in vivo use, it can be formulated in vehicles such as 10% DMSO, 40% PEG300, 5% Tween-80, and 45% saline to achieve a clear solution. The compound is stable as a powder at -20degC. As a natural product derivative, its oral bioavailability is expected to be moderate to good. Specific pharmacokinetic parameters (half-life, Cmax, AUC) have not been reported.
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| Toxicity/Toxicokinetics |
Specific toxicological data for O-allylvanillin is not available. As a derivative of vanillin, which is a widely used food flavoring agent (GRAS status), the compound is expected to have a relatively low toxicity profile. However, the addition of the allyl group may increase its reactivity and potential for toxicity. The compound should be handled with standard laboratory safety precautions, including wearing gloves, lab coat, and safety goggles, and working in a well-ventilated area. Avoid inhalation, ingestion, and skin contact.
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| References |
[1]. B Ngameni, et al. Synthesis and evaluation of anticancer activity of O-allylchalcone derivatives. Med chem 2013, 3:3
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| Additional Infomation |
O-allylvanillin (4-(allyloxy)-3-methoxybenzaldehyde; CAS 22280-95-1) is a synthetic derivative of vanillin. Vanillin is the primary component of vanilla extract and is widely used as a flavoring agent. O-allylvanillin retains the aromatic and sweet scent of vanillin while exhibiting increased reactivity due to the allyl group. This structural modification imparts unique physicochemical properties and enhances its potential for applications in organic synthesis, fragrance development, and pharmaceutical research. It is an O-allylchalcone analogue with anti-neoplastic activities, inhibiting the growth of THP-1, HL60, Hep-G2, and MCF-7 cells. The compound is not a drug and has no approved therapeutic indications. It is strictly a research-grade chemical for laboratory use.
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| Molecular Formula |
C11H12O3
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| Molecular Weight |
192.21
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| Exact Mass |
192.079
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| CAS # |
22280-95-1
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| PubChem CID |
2063823
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.084g/cm3
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| Boiling Point |
313.2ºC at 760mmHg
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| Flash Point |
134.2ºC
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| Vapour Pressure |
0.000504mmHg at 25°C
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| Index of Refraction |
1.537
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| LogP |
2.072
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
14
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| Complexity |
191
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C=CCOC1=C(C=C(C=C1)C=O)OC
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| InChi Key |
DGWCHURQYFMBFC-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C11H12O3/c1-3-6-14-10-5-4-9(8-12)7-11(10)13-2/h3-5,7-8H,1,6H2,2H3
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| Chemical Name |
3-methoxy-4-prop-2-enoxybenzaldehyde
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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) |
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 | 5.2026 mL | 26.0132 mL | 52.0264 mL | |
| 5 mM | 1.0405 mL | 5.2026 mL | 10.4053 mL | |
| 10 mM | 0.5203 mL | 2.6013 mL | 5.2026 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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