| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 25mg |
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| 50mg |
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| 100mg | |||
| Other Sizes |
| ln Vitro |
kakoul exhibited potent in vitro antifungal activity against several plant pathogenic fungi. The minimum inhibitory concentration (MIC) of kakoul against Colletotrichum orbiculare was 10 μg ml⁻¹. It also completely inhibited the mycelial growth of Botrytis cinerea at 50 μg ml⁻¹ and Cladosporium cucumerinum at 30 μg ml⁻¹. In comparison, the reference fungicide chlorothalonil had an MIC of 5 μg ml⁻¹ against C. orbiculare, miconazole had an MIC of 10 μg ml⁻¹, and nystatin had an MIC of 30 μg ml⁻¹. For B. cinerea, miconazole MIC was 10 μg ml⁻¹ and nystatin MIC was 3 μg ml⁻¹; for C. cucumerinum, miconazole MIC was 1.5 μg ml⁻¹ and nystatin MIC was 1 μg ml⁻¹. kakoul did not inhibit the mycelial growth of Alternaria mali, Fusarium oxysporum f. sp. cucumerinum, Magnaporthe grisea, Phytophthora capsici, or Rhizoctonia solani even at concentrations above 100 μg ml⁻¹. No antimicrobial activity was observed against the yeast Candida albicans and Saccharomyces cerevisiae, nor against the bacteria Bacillus subtilis, Erwinia carotovorum, Ralstonia solanacearum, and Xanthomonas campestris pv. vesicatoria at concentrations up to 100 μg ml⁻¹. [1]
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| ln Vivo |
kakoul exhibited protective activity against anthracnose disease development on cucumber (Cucumis sativus) leaves inoculated with Colletotrichum orbiculare. Treatment with kakoul at 10 μg ml⁻¹ began to protect cucumber plants from infection. At 500 μg ml⁻¹, anthracnose development was very poor. The commercial fungicide chlorothalonil was generally more effective than kakoul; no lesions were found on cucumber leaves treated with 500 μg ml⁻¹ of chlorothalonil. kakoul did not show any phytotoxic symptoms on cucumber plants even at 500 μg ml⁻¹. [1]
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| Cell Assay |
The minimum inhibitory concentrations (MICs) of kakoul against fungi, oomycete, yeasts, and bacteria were determined using a 24-well microtiter dish modification of the method described by Nair et al. Inocula were prepared as mycelial suspension of Rhizoctonia solani, spore suspensions (10⁵ spores ml⁻¹) of Alternaria mali, Botrytis cinerea, Cladosporium cucumerinum, Colletotrichum orbiculare, Fusarium oxysporum f. sp. cucumerinum, Magnaporthe grisea, and Phytophthora capsici, and cell suspensions (10⁴ CFU ml⁻¹) of Candida albicans, Saccharomyces cerevisiae, Bacillus subtilis, Erwinia carotovorum, Ralstonia solanacearum, and Xanthomonas campestris pv. vesicatoria. A 10 μl aliquot of the inoculum was added to each well containing 1 ml of potato dextrose broth. kakoul in methanol at concentrations ranging from 0 to 100 μg ml⁻¹ was dispensed into the plates. Plates inoculated with B. cinerea, C. cucumerinum, and other microorganisms were incubated at 22–28 °C. Antimicrobial activity was evaluated after 2–5 days of incubation by comparing with a positive control containing culture broth and microorganisms without kakoul. The lowest concentration at which no growth of microorganisms was observed was recorded as the MIC. Reference compounds included chlorothalonil (formulated as a 750 g kg⁻¹ wettable powder), nystatin, and miconazole. [1]
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| Animal Protocol |
The control efficacy of kakoul against anthracnose caused by Colletotrichum orbiculare on cucumber plants (Cucumis sativus L. cv Baekrokdadaki) was examined under growth chamber conditions at 28 (±2) °C with approximately 80 μmol photons m⁻² s⁻¹ (white fluorescent lamps) for 16 h per day. kakoul and chlorothalonil (750 g kg⁻¹ WP) were dissolved in methanol and water, respectively, then diluted with water containing Tween 20 (0.5 g litre⁻¹) to final concentrations of 10, 50, 100, and 500 μg ml⁻¹. Each solution was sprayed at a volume equivalent to 500 litre ha⁻¹ onto the primary and secondary leaves of cucumber plants one day before inoculation with C. orbiculare at the three-leaf stage. Control plants were sprayed with Tween 20 solution only. Inoculum was prepared by placing sterile distilled water onto the mycelial surface, then loosening spores with a sterile brush. A conidial suspension (10⁶ spores ml⁻¹) of 14-day-old C. orbiculare (cultured on potato dextrose agar at 28 °C) in Tween 20 solution (0.5 g litre⁻¹) was sprayed onto the leaves. Inoculated plants were kept in a growth chamber at approximately 100% humidity and 28 (±1) °C for 24 h, then transferred to the growth room for further incubation. Lesions on primary or secondary leaves were counted 6 days after inoculation. Data are means of lesion number per cm² leaf area of six plants. [1]
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| References | |
| Additional Infomation |
Kacuol belongs to the benzodioxane class of compounds.
kakoul is a propiphenone compound isolated from the two plant genera Asarum and Piper. Analogous propiphenones include 2-methoxy-4,5-methylenedioxypropionphenone, 2-methoxy-3,4-methylenedioxypropionphenone, and 2,4,5-trimethoxypropionphenone from Asarum, Anethum, and Piper species, respectively. kakoul has previously been reported to possess anti-histaminic activity, but this is the first report of its in vitro and in vivo antifungal activity against plant pathogens. kakoul is considered an oxidative product of saricin and safrole in the metabolic pathways of Asarum sieboldii, which show antifungal and insecticidal activity. The study suggests that kakoul itself could be developed as an agricultural fungicide or as a lead for chemical synthesis of novel fungicides. [1] |
| Molecular Formula |
C10H10O4
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|---|---|
| Molecular Weight |
194.1840
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| Exact Mass |
194.057
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| CAS # |
18607-90-4
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| PubChem CID |
596894
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| Appearance |
Off-white to light yellow solid
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
352.3±42.0 °C at 760 mmHg
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| Flash Point |
143.3±21.4 °C
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| Vapour Pressure |
0.0±0.8 mmHg at 25°C
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| Index of Refraction |
1.580
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| LogP |
2.08
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
14
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| Complexity |
228
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O1C([H])([H])OC2C([H])=C(C(C(C([H])([H])C([H])([H])[H])=O)=C([H])C1=2)O[H]
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| InChi Key |
SLLMHZXMVHNZOR-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H10O4/c1-2-7(11)6-3-9-10(4-8(6)12)14-5-13-9/h3-4,12H,2,5H2,1H3
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| Chemical Name |
1-(6-hydroxy-1,3-benzodioxol-5-yl)propan-1-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 : ~100 mg/mL (~514.99 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (12.87 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.1499 mL | 25.7493 mL | 51.4986 mL | |
| 5 mM | 1.0300 mL | 5.1499 mL | 10.2997 mL | |
| 10 mM | 0.5150 mL | 2.5749 mL | 5.1499 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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