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Demethoxyencecalin

CAS# 19013-07-1

Demethoxyencecalin

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Quality Control of Demethoxyencecalin

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Chemical structure

Demethoxyencecalin

3D structure

Chemical Properties of Demethoxyencecalin

Cas No. 19013-07-1 SDF Download SDF
PubChem ID 177040 Appearance Powder
Formula C13H14O2 M.Wt 202.3
Type of Compound Phenols Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 1-(2,2-dimethylchromen-6-yl)ethanone
SMILES CC(=O)C1=CC2=C(C=C1)OC(C=C2)(C)C
Standard InChIKey ZAJTXVHECZCXLH-UHFFFAOYSA-N
Standard InChI InChI=1S/C13H14O2/c1-9(14)10-4-5-12-11(8-10)6-7-13(2,3)15-12/h4-8H,1-3H3
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 Demethoxyencecalin

The herbs of Centaurea solstitialis L.

Biological Activity of Demethoxyencecalin

In vitro

Antifungal activity of a new phenolic compound from capitulum of a head rot-resistant sunflower genotype.[Pubmed: 18034282]

J Chem Ecol. 2007 Dec;33(12):2245-53.


METHODS AND RESULTS:
In a previous study, we observed that bract and corolla extracts from a Sclerotinia sclerotiorum-resistant sunflower contained high amounts of the known coumarins scopoletin, scopolin, and ayapin. There was a correlation between coumarin concentration and disease resistance. Thin layer chromatography showed higher concentrations of three other compounds in the resistant genotype when compared to the susceptible.
CONCLUSIONS:
A bioassay-directed purification that used column chromatography and HPLC allowed the isolation of a new compound, 3-acetyl-4-acetoxyacetophenone, and known compounds, Demethoxyencecalin and 3-acetyl-4-hydroxyacetophenone.

Accumulation and Biotransformation of Chromenes and Benzofurans in a Cell Suspension Culture of Ageratina adenophora.[Pubmed: 17269074]

Planta Med. 1987 Oct;53(5):488-92.

A cell suspension culture of AGERATINA ADENOPHORA was shown to yield several novel chromene and benzofuran derivatives in minute amounts that were different to the compounds found in seedlings of the same species. The structure elucidation of the new compounds is described.
METHODS AND RESULTS:
When two of the seedling chromenes (Demethoxyencecalin and demethylencecalin) were fed to the cell suspension culture, one biotransformation product each was obtained in high yields (80%) that originated from a hydroxylation at one of the geminal methyl groups of the chromene heterocycle. These products accumulated largely in the growth media even though the presence of cells was necessary for the biotransformations to occur. When the third seedling chromene (encecalin) was fed to the cell auspension culture, no significant biotransformation was noted but several of the benzofurans present as cell culture metabolites showed a significantly increased accumulation in the growth media of the treated cultures.
CONCLUSIONS:
This increased accumulation of benzofurans was found to be inducible also by adding yeast extract to the cell culture. The metabolism of chromenes and bezofurans in the cell suspension culture is discussed.

Protocol of Demethoxyencecalin

Structure Identification
Planta Med. 1986 Oct;(5):349-51.

[Demethoxyencecalin and Thymol derivatives from Arnica sachalinensis1.].[Pubmed: 17345336]


METHODS AND RESULTS:
From the flowers of ARNICA SACHALINENSIS the chromene Demethoxyencecalin , 10-acetoxy-8,9-epoxy-3- O-isobutyrylthymol, and 10-acetoxy-8-hydroxy-9-isobutyryloxythymol were isolated and their structures established by mass spectrometry (13)C-, and (1)H-NMR spectroscopy.

Demethoxyencecalin Dilution Calculator

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Demethoxyencecalin Molarity Calculator

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Preparing Stock Solutions of Demethoxyencecalin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.9432 mL 24.7158 mL 49.4315 mL 98.8631 mL 123.5788 mL
5 mM 0.9886 mL 4.9432 mL 9.8863 mL 19.7726 mL 24.7158 mL
10 mM 0.4943 mL 2.4716 mL 4.9432 mL 9.8863 mL 12.3579 mL
50 mM 0.0989 mL 0.4943 mL 0.9886 mL 1.9773 mL 2.4716 mL
100 mM 0.0494 mL 0.2472 mL 0.4943 mL 0.9886 mL 1.2358 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 Demethoxyencecalin

[Demethoxyencecalin and Thymol derivatives from Arnica sachalinensis1.].[Pubmed:17345336]

Planta Med. 1986 Oct;(5):349-51.

From the flowers of ARNICA SACHALINENSIS the chromene desmethoxyencecalin, 10-acetoxy-8,9-epoxy-3- O-isobutyrylthymol, and 10-acetoxy-8-hydroxy-9-isobutyryloxythymol were isolated and their structures established by mass spectrometry (13)C-, and (1)H-NMR spectroscopy.

Antifungal activity of a new phenolic compound from capitulum of a head rot-resistant sunflower genotype.[Pubmed:18034282]

J Chem Ecol. 2007 Dec;33(12):2245-53.

In a previous study, we observed that bract and corolla extracts from a Sclerotinia sclerotiorum-resistant sunflower contained high amounts of the known coumarins scopoletin, scopolin, and ayapin. There was a correlation between coumarin concentration and disease resistance. Thin layer chromatography showed higher concentrations of three other compounds in the resistant genotype when compared to the susceptible. A bioassay-directed purification that used column chromatography and HPLC allowed the isolation of a new compound, 3-acetyl-4-acetoxyacetophenone, and known compounds, Demethoxyencecalin and 3-acetyl-4-hydroxyacetophenone. Structures were assigned from spectral data, and bioactivities were characterized by in vitro bioassays against S. sclerotiorum. The new compound, 3-acetyl-4-acetoxyacetophenone, had an antifungal activity similar to the coumarin ayapin, previously described as a potent Sclerotinia inhibitor. The speed and simplicity by which these compounds can be detected make them suitable for use in screening procedures that may identify genotypes with valuable levels of resistance. A screening of seven sunflower genotypes in a field experiment showed a correlation between these compounds and resistance to Sclerotinia.

Accumulation and Biotransformation of Chromenes and Benzofurans in a Cell Suspension Culture of Ageratina adenophora.[Pubmed:17269074]

Planta Med. 1987 Oct;53(5):488-92.

A cell suspension culture of AGERATINA ADENOPHORA was shown to yield several novel chromene and benzofuran derivatives in minute amounts that were different to the compounds found in seedlings of the same species. The structure elucidation of the new compounds is described. When two of the seedling chromenes (Demethoxyencecalin and demethylencecalin) were fed to the cell suspension culture, one biotransformation product each was obtained in high yields (80%) that originated from a hydroxylation at one of the geminal methyl groups of the chromene heterocycle. These products accumulated largely in the growth media even though the presence of cells was necessary for the biotransformations to occur. When the third seedling chromene (encecalin) was fed to the cell auspension culture, no significant biotransformation was noted but several of the benzofurans present as cell culture metabolites showed a significantly increased accumulation in the growth media of the treated cultures. This increased accumulation of benzofurans was found to be inducible also by adding yeast extract to the cell culture. The metabolism of chromenes and bezofurans in the cell suspension culture is discussed.

Description

Demethoxyencecalin is a chromene isolated from Helianthus annuus, has antifungal activities.

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