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| Other Sizes |
| Targets |
Methyl eugenol inhibits the PI3K/mTOR/Akt signaling pathway. [2]
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| ln Vitro |
In RB355 human retinoblastoma cells, methyl eugenol exhibited antiproliferative activity with an IC₅₀ of 50 μM in a dose-dependent manner (0–200 μM, 48 h). [2]
- Methyl eugenol (0, 25, 50, 100 μM) induced G2/M phase cell cycle arrest in a concentration-dependent manner, with the highest increase at 100 μM. [2] - Methyl eugenol (50 μM, 24 h) induced autophagy in RB355 cells, as shown by increased accumulation of monodansylcadaverine (MDC) and acridine orange (AO) staining, indicating increased autophagosome formation and acidic vesicular organelles. [2] - Western blot analysis showed that methyl eugenol (50 μM) increased the expression of LC3-II in a time-dependent manner, while slightly decreasing p62 expression. No significant changes were observed in Vps34, Beclin-1, or LC3-I. [2] - Methyl eugenol (50 μM) abrogated the effect of the autophagy inhibitor pepstatin A (15 μg/mL), as shown by western blot. [2] - Western blot analysis revealed that methyl eugenol (0, 25, 50, 100 μM) downregulated the expression of PI3K, p-PI3K, Akt, p-Akt, mTOR, and p-mTOR in a concentration-dependent manner. [2] |
| ln Vivo |
The in vivo activity described is the attraction of male Bactrocera dorsalis (oriental fruit fly) in field settings in Hawaii.
When dispensed from bucket traps, the attractiveness of methyl eugenol was compared to mixtures with cue-lure. Captures of B. dorsalis varied with the concentration of methyl eugenol in the mixture. Traps baited with 100% methyl eugenol captured significantly more flies than those baited with 25%, 50%, or 75% methyl eugenol (mixed with cue-lure). [1] In a separate field study, three different dispensers (bucket traps with cotton wicks, canecc disks, and Min-U-Gel spots) containing methyl eugenol (8 mL) and malathion (2 mL) were weathered for 2-16 weeks under Hawaiian climatic conditions and then bioassayed for their ability to attract B. dorsalis. Initially, captures with freshly prepared dispensers were not significantly different. After weathering, bucket traps and canecc disks remained attractive for up to 16 weeks. Min-U-Gel lost its attractiveness within 2 weeks. [1] |
| Enzyme Assay |
Lactate Dehydrogenase (LDH) Assay: To assess tissue damage, serum LDH levels were measured. The measurement used a kinetic ultraviolet method, where the initial rate of NADH oxidation is directly proportional to the catalytic LDH activity, expressed in U/L. [3]
Glutathione S-transferase (GST) Assay: Tissue GST activity in the small intestine homogenate was assessed according to the manufacturer's instructions. [3] Superoxide Dismutase (SOD) Assay: SOD activity in the intestinal tissue was measured based on its ability to inhibit the reduction of nitro blue tetrazolium (NitroBT) by xanthine-xanthine oxidase. The activity was designated as unit/gm of intestinal tissue. [3] Catalase (CAT) Assay: Catalase activity was determined by incubating the tissue supernatant with H₂O₂. The reaction was stopped with a catalase inhibitor, and the color intensity of the complex formed was inversely proportional to the amount of catalase, measured at 510 nm. [3] |
| Cell Assay |
RB355 retinoblastoma cells were cultured in DMEM with 10% FBS and antibiotics (100 μg/mL streptomycin, 100 U/mL penicillin G) at 37°C, 5% CO₂. [2]
- MTT assay: Cells were seeded at 1 × 10⁶ cells/well in 96-well plates, treated with methyl eugenol (0–200 μM) for 48 h, then incubated with MTT solution (20 μL) and DMSO (500 μL) to solubilize formazan. Optical density was measured at 570 nm. [2] - Cell cycle analysis: Cells were treated with methyl eugenol (0, 25, 50, 100 μM) and analyzed using Muse™ Cell Analyzer and Muse™ Cell Cycle Kit per manufacturer’s protocol. [2] - Autophagy detection: Cells were treated with methyl eugenol (50 μM) for 24 h, then stained with MDC or AO. Images were captured under a microscope. [2] - Western blot: Cells were treated with methyl eugenol (0, 25, 50, 100 μM) for 48 h, lysed, and 20 μg protein aliquots were separated by 10% SDS-PAGE, transferred to nitrocellulose membranes, blocked with 5% BSA, probed with primary antibodies, then secondary antibodies, and detected with ECL reagent. [2] - Autophagy inhibitor experiment: Cells were pretreated with pepstatin A (15 μg/mL) for 1 h, then exposed to methyl eugenol (50 μM) for 48 h, and protein expression analyzed by western blot. [2] |
| Animal Protocol |
The study describes field protocols for evaluating the attractiveness of methyl eugenol to *Bactrocera dorsalis*.
For the lure mixture study, traps were placed on metal stakes 1 m above the ground and arranged around the periphery of a field. Traps were emptied and rebaited at weekly intervals. Lure treatments were applied to cotton wicks (3.8 cm long, 1.9 cm diameter) placed inside plastic bucket traps. Each wick contained 8 mL of the lure treatment and 2 mL of 95% technical malathion. [1] For the dispenser comparison study, methyl eugenol dispensers were weathered for 2-16 weeks at the University of Hawaii Experiment Station. At 2-week intervals, dispensers were collected, frozen, and stored until bioassay. For the bioassay, weathered dispensers were placed inside plastic bucket traps, which were then placed in guava trees at eye level and arranged in orchards in a randomized complete block design. Data were collected as the mean number of flies per trap per day. [1] The study describes field protocols for evaluating the attractiveness of methyl eugenol to Bactrocera dorsalis. For the lure mixture study, traps were placed on metal stakes 1 m above the ground and arranged around the periphery of a field. Traps were emptied and rebaited at weekly intervals. Lure treatments were applied to cotton wicks (3.8 cm long, 1.9 cm diameter) placed inside plastic bucket traps. Each wick contained 8 mL of the lure treatment and 2 mL of 95% technical malathion. [1] For the dispenser comparison study, methyl eugenol dispensers were weathered for 2-16 weeks at the University of Hawaii Experiment Station. At 2-week intervals, dispensers were collected, frozen, and stored until bioassay. For the bioassay, weathered dispensers were placed inside plastic bucket traps, which were then placed in guava trees at eye level and arranged in orchards in a randomized complete block design. Data were collected as the mean number of flies per trap per day. [1] |
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
…A study included nine healthy adult male and female volunteers. …The mean fasting level of methyleugenol in serum was 16.2 ± 4.0 pg/g wet weight. Peak plasma concentrations occurred at 15 minutes (mean ± standard deviation, 53.9 ± 7.3 pg/g wet weight), followed by a rapid decline; the elimination half-life was approximately 90 minutes. This peak level is consistent with the range of methyleugenol plasma concentrations in the US population, which were measured simultaneously in non-fasting participants during the Third National Health and Nutrition Examination Survey (NHANES III). Metabolism/Metabolites In rats, the allyl side chain of eugenol methyl ether undergoes oxidation to produce three metabolites, two of which are excreted as glycine conjugates. Other metabolic reactions include benzene ring hydroxylation, ortho-demethylation, and two oxidation reactions; accounting for 63–95% of the initial dose. Most metabolites are present in bile. It is known that the human metabolite of methyl eugenol includes 1-hydroxymethyl eugenol. Biological half-life ...The human elimination half-life is approximately 90 minutes. |
| Toxicity/Toxicokinetics |
Toxicity Data
LC50 (Rat) > 4,800 mg/m3 Non-human Toxicity Values LD50 Rabbit dermal administration > 2025 mg/kg LD50 Rat oral administration 1179 mg/kg LD50 Mouse intraperitoneal injection 540 mg/kg LD50 Mouse intravenous injection 112 mg/kg LD50 Mouse intraperitoneal injection > 640 mg/kg /table/ Carcinogenicity: Previous studies indicated that methyl eugenol induced carcinogenic activity in different organs of F344 rats and B6C3F1 mice at a dose range of 150-300 mg/kg/day. [3] Subchronic Toxicity: Other studies reported toxic effects at subchronic doses for 14 weeks, including hepatocellular damage, cholestasis, altered hepatic functions, hypoproteinemia, hypoalbuminemia, atrophic gastritis, and adrenal gland cortical hypertrophy. [3] LD50: The LD50 of methyl eugenol was previously measured to be 850-1560 mg/kg. The dose used in this study (100 mg/kg/day) is far from this LD50 range. [3] |
| References |
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| Additional Infomation |
According to the National Toxicology Program (NTP), methyleugenol is a potential carcinogen. Methyleugenol is a clear, colorless to pale yellow liquid with a pungent, earthy odor and a bitter, burning taste. (NTP, 1992) o-Methyleugenol is a phenylpropanoid compound whose function is related to eugenol. Methyleugenol has been reported in Magnolia officinalis, Taxus chinensis, and other organisms with relevant data. Methyleugenol is a pale yellow, oily natural liquid with a clove-like aroma and is found in many essential oils. Methyleugenol is used as a flavoring agent, spice, and rodent anesthetic. Methyleugenol is mutagenic in animals, and based on evidence of carcinogenicity in animals, there is reason to expect it to be carcinogenic in humans as well. (NCI05) Methyleugenol is found in Allspice. Methyleugenol is found in many essential oils, such as nutmeg and nutmeg peel, and in many fruits, such as apples, bananas, orange juice or peel, grapefruit, and blueberries. Methyleugenol has been shown to have analgesic effects (A7914). Methyleugenol belongs to the anisole class of compounds. Anisole compounds are organic compounds containing methoxybenzene or its derivatives.
Therapeutic Uses Anesthetics Drugs (Veterinary): Methyleugenol, suspended in Tween-80 or polyoxyethylene ether, can be safely administered intraperitoneally at doses of 200 to 275 mg/kg to rats and mice undergoing brain surgery without some of the inconveniences of sodium pentobarbital. Methyl eugenol is a plant-derived phenylpropenoid compound mainly isolated from Eugenia caryophyllata (clove). [2] - It has reported antimicrobial and anticancer activities. [2] - This study demonstrates that methyl eugenol induces antiproliferative effects, G2/M cell cycle arrest, and autophagy in retinoblastoma RB355 cells via inhibition of the PI3K/mTOR/Akt signaling pathway. [2] - The IC₅₀ value of 50 μM was lower than that of several other anticancer compounds, suggesting potential as a lead molecule for retinoblastoma therapy. [2] |
| Molecular Formula |
C11H14O2
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|---|---|
| Molecular Weight |
178.23
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| Exact Mass |
178.099
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| CAS # |
93-15-2
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| Related CAS # |
Methyl Eugenol-13C,d3
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| PubChem CID |
7127
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| Appearance |
Colorless to light yellow liquid
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
254.7±0.0 °C at 760 mmHg
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| Melting Point |
−4 °C(lit.)
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| Flash Point |
87.1±22.7 °C
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| Vapour Pressure |
0.0±0.5 mmHg at 25°C
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| Index of Refraction |
1.500
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| LogP |
2.97
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
13
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| Complexity |
156
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O(C)C1C(OC)=CC(CC=C)=CC=1
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| InChi Key |
ZYEMGPIYFIJGTP-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4,6-8H,1,5H2,2-3H3
|
| Chemical Name |
1,2-dimethoxy-4-prop-2-enylbenzene
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| Synonyms |
Methyl eugenol Eugenol methyl etherMethyleugenol O-Methyleugenol 3,4-Dimethoxyallylbenzene4-Allylveratrole
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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 (~561.07 mM)
H2O : < 0.1 mg/mL |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (14.03 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 (14.03 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 (14.03 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 | 5.6107 mL | 28.0536 mL | 56.1073 mL | |
| 5 mM | 1.1221 mL | 5.6107 mL | 11.2215 mL | |
| 10 mM | 0.5611 mL | 2.8054 mL | 5.6107 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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