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Methyleugenol

Alias: Methyl eugenol Eugenol methyl etherMethyleugenol O-Methyleugenol 3,4-Dimethoxyallylbenzene4-Allylveratrole
Cat No.:V8311 Purity: ≥98%
Methyl Eugenol is a phenylpropanoid found in plant leaves, fruits, stems and/or roots and is released when the corresponding plant parts are damaged by herbivore feeding.
Methyleugenol
Methyleugenol Chemical Structure CAS No.: 93-15-2
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Other Forms of Methyleugenol:

  • Methyl Eugenol-13C,d3
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Methyl Eugenol is a phenylpropanoid found in plant leaves, fruits, stems and/or roots and is released when the corresponding plant parts are damaged by herbivore feeding. Methyl Eugenol may be utilized to eliminate male Oriental fruit flies.
Biological Activity I Assay Protocols (From Reference)
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]
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/
References

[1]. Methyl eugenol and cue-lure traps for suppression of male oriental fruit flies and melon flies (Diptera: Tephritidae) in Hawaii: effects of lure mixtures and weathering. Journal of economic entomology vol. 93,1 (2000): 81-7.

[2]. Methyl eugenol induces potent anticancer effects in RB355 human retinoblastoma cells by inducing autophagy, cell cycle arrest and inhibition of PI3K/mTOR/Akt signalling pathway. Journal of B.U.ON. : official journal of the Balkan Union of Oncology vol. 23,4 (2018): 1174-1178.

[3]. Mechanism underlying methyl eugenol attenuation of intestinal ischemia/reperfusion injury. Applied physiology, nutrition, and metabolism = Physiologie appliquee, nutrition et metabolisme vol. 42,10 (2017): 1097-1105.

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.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C11H14O2
Molecular Weight
178.23
Exact Mass
178.099
CAS #
93-15-2
Related CAS #
Methyl Eugenol-13C,d3
PubChem CID
7127
Appearance
Colorless to light yellow liquid
Density
1.0±0.1 g/cm3
Boiling Point
254.7±0.0 °C at 760 mmHg
Melting Point
−4 °C(lit.)
Flash Point
87.1±22.7 °C
Vapour Pressure
0.0±0.5 mmHg at 25°C
Index of Refraction
1.500
LogP
2.97
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
4
Heavy Atom Count
13
Complexity
156
Defined Atom Stereocenter Count
0
SMILES
O(C)C1C(OC)=CC(CC=C)=CC=1
InChi Key
ZYEMGPIYFIJGTP-UHFFFAOYSA-N
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
Synonyms
Methyl eugenol Eugenol methyl etherMethyleugenol O-Methyleugenol 3,4-Dimethoxyallylbenzene4-Allylveratrole
HS Tariff Code
2934.99.9001
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)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~561.07 mM)
H2O : < 0.1 mg/mL
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.

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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.
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 5.6107 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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