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o-Methoxycinnamaldehyde

CAS# 1504-74-1

o-Methoxycinnamaldehyde

2D Structure

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3D structure

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o-Methoxycinnamaldehyde

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Chemical Properties of o-Methoxycinnamaldehyde

Cas No. 1504-74-1 SDF Download SDF
PubChem ID 641298 Appearance White-pale yellow crystals
Formula C10H10O2 M.Wt 162.2
Type of Compound Phenols Storage Desiccate at -20°C
Synonyms o-Methoxycinnamic aldehyde
Solubility Soluble in ethanol and methan
Chemical Name (E)-3-(2-methoxyphenyl)prop-2-enal
SMILES COC1=CC=CC=C1C=CC=O
Standard InChIKey KKVZAVRSVHUSPL-GQCTYLIASA-N
Standard InChI InChI=1S/C10H10O2/c1-12-10-7-3-2-5-9(10)6-4-8-11/h2-8H,1H3/b6-4+
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 o-Methoxycinnamaldehyde

The barks of Cinnamomum cassia Presl

Biological Activity of o-Methoxycinnamaldehyde

Descriptiono-Methoxycinnamaldehyde from cinnamon has antibiotic activity, it is a competitive inhibitor against CYP1A2 while it was a mixed type inhibitor against CYP2E.
TargetsP450 (e.g. CYP17)
In vivo

Metabolism of the cinnamon constituent o-methoxycinnamaldehyde in the rat.[Pubmed: 3765663]

Xenobiotica. 1986 Sep;16(9):845-52.


METHODS AND RESULTS:
The metabolism of o-Methoxycinnamaldehyde (1.3 mmol/kg, intragastrically) was studied in rats. Identification of the urinary metabolites by g.l.c.-mass spectrometry and quantification by h.p.l.c. showed that the major metabolic pathway (approx. two-thirds of the dose) was oxidation to the corresponding cinnamic and phenylpropionic acids (C6-C3 acids) which were largely excreted as glycine conjugates. Intermediate amounts (approx. 10% of the dose) of the O-demethylated C6-C3 acids were excreted. Relatively large amounts of the beta-hydroxylated phenylpropionic acid derivative were found, however only traces of the further products of beta-oxidation (2-methoxylated derivatives of benzoic and hippuric acid) were excreted.
CONCLUSIONS:
No evidence was obtained for conjugation of o-Methoxycinnamaldehyde with glutathione. Urinary excretion of metabolites was rapid (91% in 24 h and 98% in 48 h).

Protocol of o-Methoxycinnamaldehyde

Kinase Assay

Identification of inhibitory component in cinnamon--O-methoxycinnamaldehyde inhibits CYP1A2 and CYP2E1-.[Pubmed: 15618674]

Drug Metabolism & Pharmacokinetics, 2002, 17(3):229-36.

The Cinnamomi Cortex and Ephedra Herba were found to more strongly inhibit aminopyrine N-demethylation in rat liver microsomes compared to other constituents included in Sho-seiryu-to.
METHODS AND RESULTS:
The component inhibiting drug oxidations catalyzed by CYP1A2 and CYP2E1 was isolated from Cinnamomi Cortex, and was identified as o-Methoxycinnamaldehyde (OMCA). When phenacetin and 4-nitrophenol were used as probe substrates for CYP1A2 and CYP2E1, respectively, the OMCA was shown to be a competitive inhibitor against CYP1A2 while it was a mixed type inhibitor against CYP2E1.
CONCLUSIONS:
The inhibitory effect of OMCA on 4-nitrophenol 2-hydroxylation (K(i)=6.3 microM) was somewhat potent compared to that observed on phenacetin O-deethylation (K(i)=13.7 microM) in rat liver microsomes.

o-Methoxycinnamaldehyde Dilution Calculator

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o-Methoxycinnamaldehyde Molarity Calculator

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Preparing Stock Solutions of o-Methoxycinnamaldehyde

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 6.1652 mL 30.8261 mL 61.6523 mL 123.3046 mL 154.1307 mL
5 mM 1.233 mL 6.1652 mL 12.3305 mL 24.6609 mL 30.8261 mL
10 mM 0.6165 mL 3.0826 mL 6.1652 mL 12.3305 mL 15.4131 mL
50 mM 0.1233 mL 0.6165 mL 1.233 mL 2.4661 mL 3.0826 mL
100 mM 0.0617 mL 0.3083 mL 0.6165 mL 1.233 mL 1.5413 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 o-Methoxycinnamaldehyde

Metabolism of the cinnamon constituent o-methoxycinnamaldehyde in the rat.[Pubmed:3765663]

Xenobiotica. 1986 Sep;16(9):845-52.

The metabolism of o-Methoxycinnamaldehyde (1.3 mmol/kg, intragastrically) was studied in rats. Identification of the urinary metabolites by g.l.c.-mass spectrometry and quantification by h.p.l.c. showed that the major metabolic pathway (approx. two-thirds of the dose) was oxidation to the corresponding cinnamic and phenylpropionic acids (C6-C3 acids) which were largely excreted as glycine conjugates. Intermediate amounts (approx. 10% of the dose) of the O-demethylated C6-C3 acids were excreted. Relatively large amounts of the beta-hydroxylated phenylpropionic acid derivative were found, however only traces of the further products of beta-oxidation (2-methoxylated derivatives of benzoic and hippuric acid) were excreted. No evidence was obtained for conjugation of o-Methoxycinnamaldehyde with glutathione. Urinary excretion of metabolites was rapid (91% in 24 h and 98% in 48 h).

Identification of inhibitory component in cinnamon--O-methoxycinnamaldehyde inhibits CYP1A2 and CYP2E1-.[Pubmed:15618674]

Drug Metab Pharmacokinet. 2002;17(3):229-36.

The Cinnamomi Cortex and Ephedra Herba were found to more strongly inhibit aminopyrine N-demethylation in rat liver microsomes compared to other constituents included in Sho-seiryu-to. The component inhibiting drug oxidations catalyzed by CYP1A2 and CYP2E1 was isolated from Cinnamomi Cortex, and was identified as o-Methoxycinnamaldehyde (OMCA). When phenacetin and 4-nitrophenol were used as probe substrates for CYP1A2 and CYP2E1, respectively, the OMCA was shown to be a competitive inhibitor against CYP1A2 while it was a mixed type inhibitor against CYP2E1. The inhibitory effect of OMCA on 4-nitrophenol 2-hydroxylation (K(i)=6.3 microM) was somewhat potent compared to that observed on phenacetin O-deethylation (K(i)=13.7 microM) in rat liver microsomes.

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