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trans-Methylisoeugenol

CAS# 6379-72-2

trans-Methylisoeugenol

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Chemical structure

trans-Methylisoeugenol

3D structure

Chemical Properties of trans-Methylisoeugenol

Cas No. 6379-72-2 SDF Download SDF
PubChem ID 637776 Appearance Oil
Formula C11H14O2 M.Wt 178.2
Type of Compound Phenylpropanoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 1,2-dimethoxy-4-[(E)-prop-1-enyl]benzene
SMILES CC=CC1=CC(=C(C=C1)OC)OC
Standard InChIKey NNWHUJCUHAELCL-SNAWJCMRSA-N
Standard InChI InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4-8H,1-3H3/b5-4+
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of trans-Methylisoeugenol

The roots of Atractylodes macrocephala

Biological Activity of trans-Methylisoeugenol

Description1. Eugenol methyl ether(trans-Methylisoeugenol) can cause moderate reversible inhibition of glutathione S-transferases (GSTs)(I25 ranged from 0.2 to 5.4 mM for human GSTs and from 0.4 to 4.9 mM for rat GSTs). 2.The use of isoeugenol methyl ether(trans-Methylisoeugenol) is described as an agent to inhibit and/or prevent the growth of and/or to destroy micro-organisms causing bad breath and/or to combat bad breath. 3.(E)-Methyl isoeugenol (trans-Methylisoeugenol) is a natural food flavour, it also has anxiolytic and antidepressant like properties.
Targets5-HT Receptor

trans-Methylisoeugenol Dilution Calculator

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trans-Methylisoeugenol Molarity Calculator

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Preparing Stock Solutions of trans-Methylisoeugenol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.6117 mL 28.0584 mL 56.1167 mL 112.2334 mL 140.2918 mL
5 mM 1.1223 mL 5.6117 mL 11.2233 mL 22.4467 mL 28.0584 mL
10 mM 0.5612 mL 2.8058 mL 5.6117 mL 11.2233 mL 14.0292 mL
50 mM 0.1122 mL 0.5612 mL 1.1223 mL 2.2447 mL 2.8058 mL
100 mM 0.0561 mL 0.2806 mL 0.5612 mL 1.1223 mL 1.4029 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on trans-Methylisoeugenol

Anxiolytic and antidepressant like effects of natural food flavour (E)-methyl isoeugenol.[Pubmed:24920211]

Food Funct. 2014 Aug;5(8):1819-28.

(E)-methyl isoeugenol (MIE) is a natural food flavour that constitutes 93.7% of an essential oil from Pimenta pseudocaryophyllus leaf. The leaf extracts of this species are used as a calming agent. As a ubiquitous food additive, the application of MIE for treating mood disorders appears to be globally attractive. Hence, we sought to evaluate general pharmacological activities, anticonvulsant, anxiolytic and antidepressant effects and the possible mechanisms of MIE actions. Administration of MIE was carried out prior to the exposure of a male Swiss mice to general behavioural tests, barbiturate sleep, PTZ-induced convulsion, light dark box (LDB), elevated plus maze (EPM), wire hanging, open field (OF) and forced swimming test (FST). The involvement of monoamine system was studied by mice pretreatment with WAY100635 (antagonist of 5-HT1A), alpha-methyl-p-tyrosine (AMPT; depletor of catecholamine) or p-chlorophenylalanine (PCPA; depletor of serotonin storage). There was no record of neurotoxic effect or animal's death during the course of general pharmacological tests. MIE at 250 and 500 mg kg(-1) potentiated the hypnotic effect of sodium pentobarbital. However, MIE did not protect against PTZ-induced convulsion. Except for MIE at 500 mg kg(-1), parameters evaluated in the LDB, EPM and OF demonstrated an anxiolytic like property of MIE. This effect was blocked by WAY100635 pretreatment. MIE at 500 mg kg(-1) elicited a reduction in locomotor activity of the mice in the OF. Anti-immobility effect of MIE 250 mg kg(-1) in the FST suggested an antidepressive like property. Unlike AMPT, pretreatment with PCPA reversed the antidepressant like effect of MIE. Our findings demonstrated anxiolytic and antidepressant like properties of (E)-methyl isoeugenol and suggested the participation of serotonergic pathways.

Inhibition of rat, mouse, and human glutathione S-transferase by eugenol and its oxidation products.[Pubmed:8620581]

Chem Biol Interact. 1996 Jan 5;99(1-3):85-97.

The irreversible and reversible inhibition of glutathione S-transferases (GSTs) by eugenol was studied in rat, mouse and man. Using liver cytosol of human, rat and mouse, species differences were found in the rate of irreversible inhibition of GSTs by eugenol in the presence of the enzyme tyrosinase. Tyrosinase was used to oxidize eugenol. No inhibition was observed in the absence of tyrosinase. The rate of irreversible inhibition of GSTs was highest in mouse cytosol, and lowest in rat cytosol. In addition, the irreversible inhibition of human and rat GSTs by eugenol was studied using purified isoenzymes of man and rat. The human GST isoenzymes A1-1, M1a-1a and P1-1 and the rat GST isoenzymes 1-1, 2-2, 3-3, 4-4 and 7-7 were irreversibly inhibited by eugenol in the presence of tyrosinase. In this respect human GST P1-1 and rat GST 7-7 were by far the most sensitive enzymes; human GST A2-2 was not inhibited. Indications were found that human GST P1-1 may be inhibited via three mechanisms: in addition to the well documentated nucleophilic addition of quinones and oxidation of cysteine residues, a covalent subunit cross-linking was also observed. The reversible inhibition of human and rat GST by eugenol, eugenol methyl ether, isoeugenol methyl ether, 2-allylphenol and 4-propylphenol was also studied using purified isoenzymes. The reversible inhibition of human and rat GSTs, using 1-chloro-2,4-dinitrobenzene as substrate, was expressed as I25. All compounds caused moderate reversible inhibition (I25 ranged from 0.2 to 5.4 mM for human GSTs and from 0.4 to 4.9 mM for rat GSTs). In rat, eugenol methyl ether was the strongest inhibitor. In human, the overall inhibiting capacities of eugenol, eugenol methyl ether, isoeugenol methyl ether and 4-propyl phenol were more or less similar; 2-allylphenol was the poorest inhibitor.

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