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alpha-Conidendrin

CAS# 85699-62-3

alpha-Conidendrin

Catalog No. BCN4407----Order now to get a substantial discount!

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alpha-Conidendrin: 5mg $903 In Stock
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Quality Control of alpha-Conidendrin

Number of papers citing our products

Chemical structure

alpha-Conidendrin

3D structure

Chemical Properties of alpha-Conidendrin

Cas No. 85699-62-3 SDF Download SDF
PubChem ID 369613 Appearance Powder
Formula C20H20O6 M.Wt 356.4
Type of Compound Lignans Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (3aS)-7-hydroxy-9-(4-hydroxy-3-methoxyphenyl)-6-methoxy-3a,4,9,9a-tetrahydro-1H-benzo[f][2]benzofuran-3-one
SMILES COC1=C(C=C2C(C3COC(=O)C3CC2=C1)C4=CC(=C(C=C4)O)OC)O
Standard InChIKey CAYMSCGTKZIVTN-CDJWAVJASA-N
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 alpha-Conidendrin

The barks of Tsuga dumosa

Biological Activity of alpha-Conidendrin

In vitro

Cytotoxic responses to aromatic ring and configurational variations in alpha-conidendrin, podophyllotoxin, and sikkimotoxin derivatives.[Pubmed: 11170627]

J Med Chem. 2001 Jan 18;44(2):180-5.

Derivatives of alpha-Conidendrin, podophyllotoxin, and sikkimotoxin were prepared to evaluate the cytotoxic contributions of C-4 configuration and pendant and fused arene substitutions.
METHODS AND RESULTS:
Dimethyl-alpha-conidendryl alcohol (5), 9-deoxypodophyllol (6), and 9-deoxysikkimol (17) were dehydrated to their respective oxolane derivatives 4, 3, and 9. Diols 5 and 6 were converted via oxabicyclo[3.2.1]octanols 10 and 14 to target oxolanes 8 and 7 where C-4 had been inverted relative to that in 3 and 4. Cytotoxicities of the five oxolanes were determined in two drug-sensitive human leukemia and two multidrug-resistant cell lines expressing P-glycoprotein or multidrug-resistance associated protein (MRP). Changing the pendant arene configuration or replacing a m-methoxy by hydrogen resulted in a 100-fold cytotoxicity loss. Replacing a methylenedioxy group in the fused arene by two methoxy substituents reduced cytotoxicity by 10-fold.
CONCLUSIONS:
Drug-resistant cell lines were equally resistant to compounds 3, 4, 8, and 9 indicating that these four compounds do not serve as substrates of the transport proteins P-glycoprotein and MRP.

Protocol of alpha-Conidendrin

Structure Identification
J Nat Prod. 2004 Apr;67(4):697-9.

Alpha-conidendrin as a source for preparation of sikkimotoxin derivatives.[Pubmed: 15104508]


METHODS AND RESULTS:
Oxidation of alpha-Conidendrin (3) by Fremy's salt favored formation of an o-quinone (4) at the pendant aromatic ring as opposed to the fused aromatic ring. Quinone reduction and phenolic methylation, followed by lactone reduction, and subsequent oxidation by dichlorodicyanoquinone produced sikkimotoxin oxabicyclooctane (7), while oxidation with cupric sulfate/potassium persulfate gave sikkimotoxin dioxatricyclodecane (8).

alpha-Conidendrin Dilution Calculator

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alpha-Conidendrin Molarity Calculator

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Preparing Stock Solutions of alpha-Conidendrin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.8058 mL 14.0292 mL 28.0584 mL 56.1167 mL 70.1459 mL
5 mM 0.5612 mL 2.8058 mL 5.6117 mL 11.2233 mL 14.0292 mL
10 mM 0.2806 mL 1.4029 mL 2.8058 mL 5.6117 mL 7.0146 mL
50 mM 0.0561 mL 0.2806 mL 0.5612 mL 1.1223 mL 1.4029 mL
100 mM 0.0281 mL 0.1403 mL 0.2806 mL 0.5612 mL 0.7015 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 alpha-Conidendrin

Cytotoxic responses to aromatic ring and configurational variations in alpha-conidendrin, podophyllotoxin, and sikkimotoxin derivatives.[Pubmed:11170627]

J Med Chem. 2001 Jan 18;44(2):180-5.

Derivatives of alpha-Conidendrin, podophyllotoxin, and sikkimotoxin were prepared to evaluate the cytotoxic contributions of C-4 configuration and pendant and fused arene substitutions. Dimethyl-alpha-conidendryl alcohol (5), 9-deoxypodophyllol (6), and 9-deoxysikkimol (17) were dehydrated to their respective oxolane derivatives 4, 3, and 9. Diols 5 and 6 were converted via oxabicyclo[3.2.1]octanols 10 and 14 to target oxolanes 8 and 7 where C-4 had been inverted relative to that in 3 and 4. Cytotoxicities of the five oxolanes were determined in two drug-sensitive human leukemia and two multidrug-resistant cell lines expressing P-glycoprotein or multidrug-resistance associated protein (MRP). Changing the pendant arene configuration or replacing a m-methoxy by hydrogen resulted in a 100-fold cytotoxicity loss. Replacing a methylenedioxy group in the fused arene by two methoxy substituents reduced cytotoxicity by 10-fold. Drug-resistant cell lines were equally resistant to compounds 3, 4, 8, and 9 indicating that these four compounds do not serve as substrates of the transport proteins P-glycoprotein and MRP.

Alpha-conidendrin as a source for preparation of sikkimotoxin derivatives.[Pubmed:15104508]

J Nat Prod. 2004 Apr;67(4):697-9.

Oxidation of alpha-Conidendrin (3) by Fremy's salt favored formation of an o-quinone (4) at the pendant aromatic ring as opposed to the fused aromatic ring. Quinone reduction and phenolic methylation, followed by lactone reduction, and subsequent oxidation by dichlorodicyanoquinone produced sikkimotoxin oxabicyclooctane (7), while oxidation with cupric sulfate/potassium persulfate gave sikkimotoxin dioxatricyclodecane (8).

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