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7-Epi 10-Desacetyl Paclitaxel

Microtubule polymer stabilizer,inhibits cancer cell growth CAS# 78454-17-8

7-Epi 10-Desacetyl Paclitaxel

Catalog No. BCC1314----Order now to get a substantial discount!

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Quality Control of 7-Epi 10-Desacetyl Paclitaxel

Number of papers citing our products

Chemical structure

7-Epi 10-Desacetyl Paclitaxel

3D structure

Chemical Properties of 7-Epi 10-Desacetyl Paclitaxel

Cas No. 78454-17-8 SDF Download SDF
PubChem ID 14355298 Appearance Powder
Formula C45H49NO13 M.Wt 811.87
Type of Compound Diterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES CC1=C2C(C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1OC(=O)C(C(C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)O)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)O)C)O
Standard InChIKey TYLVGQKNNUHXIP-DIYBZAJCSA-N
Standard InChI InChI=1S/C45H49NO13/c1-24-29(57-41(54)35(50)33(26-15-9-6-10-16-26)46-39(52)27-17-11-7-12-18-27)22-45(55)38(58-40(53)28-19-13-8-14-20-28)36-43(5,37(51)34(49)32(24)42(45,3)4)30(48)21-31-44(36,23-56-31)59-25(2)47/h6-20,29-31,33-36,38,48-50,55H,21-23H2,1-5H3,(H,46,52)/t29-,30+,31+,33-,34+,35+,36-,38-,43+,44-,45+/m0/s1
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 7-Epi 10-Desacetyl Paclitaxel

The barks of Taxus wallichiana.

Biological Activity of 7-Epi 10-Desacetyl Paclitaxel

Description7-Epi-10-deacetyltaxol shows IC50 values of 0.085 nM, against HeLa cells.
In vitro

α-Glucosidase Inhibitory and Cytotoxic Taxane Diterpenoids from the Stem Bark of Taxus wallichiana.[Pubmed: 28240909]

J Nat Prod. 2017 Apr 28;80(4):1087-1095.

From a CH2Cl2 extract of the bark of Taxus wallichiana, six new taxoids, wallitaxanes A-F (1-6), were isolated, together with 29 known compounds.
METHODS AND RESULTS:
The structures of the new compounds were elucidated on the basis of spectroscopic data interpretation. Wallitaxane D (4) was identified as an opened oxetane-type taxoid having the first naturally occurring C(H)-20 acetal group, while wallitaxanes E (5) and F (6) are representative of the rare abeo-taxoid class. The isolated compounds were evaluated for their α-glucosidase inhibitory activity and for cytotoxicity against the HeLa human cervical cancer cell line.
CONCLUSIONS:
In the present work, taxanes were found to exhibit α-glucosidase inhibitory activity for the first time, and wallitaxane A (1) showed the most potent effect, with an IC50 value of 3.6 μM. In turn, 7-epi-taxol (16) and 7-Epi-10-deacetyltaxol (17) showed IC50 values of 0.05 and 0.085 nM, respectively, against HeLa cells.

Protocol of 7-Epi 10-Desacetyl Paclitaxel

Structure Identification
Biomed Chromatogr. 2009 Jan;23(1):63-70.

Simultaneous determination of main taxoids in Taxus needles extracts by solid-phase extraction-high-performance liquid chromatography with pentafluorophenyl column.[Pubmed: 18816506 ]


METHODS AND RESULTS:
A simple and accurate RP-HPLC method with pentafluorophenyl (PFP) column was developed for the simultaneous determination of six taxoids, i.e. paclitaxel, 10-deacetylbaccatin III (10-DAB III), 7-xylosyl-10-deacetyltaxol (7-xyl-10-DAT), 10-deacetyltaxol (10-DAT), cephalomannine and 7-Epi-10-deacetyltaxol (7-epi-10-DAT), in the extracts from the needles of three Taxus species. The mobile phase consisted of acetonitrile (A) and water (B), and the extracts were separated using gradient elution program: 30% A at the first 7 min, and then ramped to 42% A at 8 min, held until 38 min. The developed method was validated with satisfactory precision (RSD < 2.61%), repeatability (RSD < 2.92%) and recovery (95.19-104.47%). The above taxoids in the extracts of Taxus cuspidata, T. chinensis and T. media were analyzed with the developed RP-HPLC method, and the results showed that the contents of different taxoids in three mentioned species were distinct. Maximal amounts of 10-DAB III, 7-xyl-10-DAT and 7-epi-10-DAT appeared in T. chinensis, while T. media possessed the highest content of 10-DAT, cephalomannine and paclitaxel. The developed method is accurate and efficient.
CONCLUSIONS:
It can be reliably used in the improved determination of taxoids for the quality control of Taxus species.

7-Epi 10-Desacetyl Paclitaxel Dilution Calculator

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7-Epi 10-Desacetyl Paclitaxel Molarity Calculator

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Preparing Stock Solutions of 7-Epi 10-Desacetyl Paclitaxel

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.2317 mL 6.1586 mL 12.3172 mL 24.6345 mL 30.7931 mL
5 mM 0.2463 mL 1.2317 mL 2.4634 mL 4.9269 mL 6.1586 mL
10 mM 0.1232 mL 0.6159 mL 1.2317 mL 2.4634 mL 3.0793 mL
50 mM 0.0246 mL 0.1232 mL 0.2463 mL 0.4927 mL 0.6159 mL
100 mM 0.0123 mL 0.0616 mL 0.1232 mL 0.2463 mL 0.3079 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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Background on 7-Epi 10-Desacetyl Paclitaxel

Paclitaxel impurity. Paclitaxel is a compound extracted from the Pacific yew tree with antineoplastic activity. Paclitaxel binds to tubulin and inhibits the disassembly of microtubules, thereby resulting in the inhibition of cell division. Paclitaxel also induces apoptosis by binding to and blocking the function of the apoptosis inhibitor protein Bcl-2 (B-cell Leukemia 2). Paclitaxel inhibits DNA synthesis and stimulates the release of tumor necrosis factor-α. Paclitaxel induces apoptosis in murine mammary carcinoma MCA-4 and ovarian carcinoma OCA-1 tumors.

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References on 7-Epi 10-Desacetyl Paclitaxel

alpha-Glucosidase Inhibitory and Cytotoxic Taxane Diterpenoids from the Stem Bark of Taxus wallichiana.[Pubmed:28240909]

J Nat Prod. 2017 Apr 28;80(4):1087-1095.

From a CH2Cl2 extract of the bark of Taxus wallichiana, six new taxoids, wallitaxanes A-F (1-6), were isolated, together with 29 known compounds. The structures of the new compounds were elucidated on the basis of spectroscopic data interpretation. Wallitaxane D (4) was identified as an opened oxetane-type taxoid having the first naturally occurring C(H)-20 acetal group, while wallitaxanes E (5) and F (6) are representative of the rare abeo-taxoid class. The isolated compounds were evaluated for their alpha-glucosidase inhibitory activity and for cytotoxicity against the HeLa human cervical cancer cell line. In the present work, taxanes were found to exhibit alpha-glucosidase inhibitory activity for the first time, and wallitaxane A (1) showed the most potent effect, with an IC50 value of 3.6 muM. In turn, 7-epi-taxol (16) and 7-epi-10-deacetyltaxol (17) showed IC50 values of 0.05 and 0.085 nM, respectively, against HeLa cells.

Simultaneous determination of main taxoids in Taxus needles extracts by solid-phase extraction-high-performance liquid chromatography with pentafluorophenyl column.[Pubmed:18816506]

Biomed Chromatogr. 2009 Jan;23(1):63-70.

A simple and accurate RP-HPLC method with pentafluorophenyl (PFP) column was developed for the simultaneous determination of six taxoids, i.e. paclitaxel, 10-deacetylbaccatin III (10-DAB III), 7-xylosyl-10-deacetyltaxol (7-xyl-10-DAT), 10-deacetyltaxol (10-DAT), cephalomannine and 7-epi-10-deacetyltaxol (7-epi-10-DAT), in the extracts from the needles of three Taxus species. The mobile phase consisted of acetonitrile (A) and water (B), and the extracts were separated using gradient elution program: 30% A at the first 7 min, and then ramped to 42% A at 8 min, held until 38 min. The developed method was validated with satisfactory precision (RSD < 2.61%), repeatability (RSD < 2.92%) and recovery (95.19-104.47%). The above taxoids in the extracts of Taxus cuspidata, T. chinensis and T. media were analyzed with the developed RP-HPLC method, and the results showed that the contents of different taxoids in three mentioned species were distinct. Maximal amounts of 10-DAB III, 7-xyl-10-DAT and 7-epi-10-DAT appeared in T. chinensis, while T. media possessed the highest content of 10-DAT, cephalomannine and paclitaxel. The developed method is accurate and efficient. It can be reliably used in the improved determination of taxoids for the quality control of Taxus species.

Description

7-Epi 10-desacetyl paclitaxel (7-epi-10-deacetyltaxol), a taxol derivative, exhibits cytotoxicity against HeLa cells with an IC50 of 85 μM.

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