10-Deacetylbaccatin III

Names

[ Name ]:
10-Deacetylbaccatin III

[Synonym ]:
10-Dab
10-DAB (10-Deacetylbaccatin)
MFCD00132913
EINECS 418-680-6
(2α,5β,7β,10α,13α)-4-Acetoxy-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate
(2α,5β,7β,10β,13α)-4-(acetyloxy)-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate
10-Deacetylbaccatine
10-deacetylbaccatin11
10-DAB-III
10DBA III
10-Deacetyl
10-DEACETYLBACCATIN
10-Deacetylbaccatin-III
10-desacetylbaccatin III
10-Deacetylbaccatin III
DESACETYLBACCATINE
Docetaxel impurity E
7,11-Methano-5H-cyclodeca[3,4]benz[1,2-b]oxet-5-one, 12b-(acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,6,9,11-tetrahydroxy-4a,8,13,13-tetramethyl-, (2aR,4S,4aS,6S,9S,11S,12S,12aR,12bS)-
(2α,5β,7β,10β,13α)-4-Acetoxy-1,7,10,13-tetrahydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate
7,11-Methano-5H-cyclodeca[3,4]benz[1,2-b]oxet-5-one, 12b-(acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,6,9,11-tetrahydroxy-4a,8,13,13-tetramethyl-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-

Biological Activity

[Description]:

10-Deacetylbaccatin-III is an intermediate for taxol analog preparations. IC50 value:Target: Taxols have exhibit antitumor agents. Several of these taxols can be synthesized from 10- Deacetylbaccatin-III. 10-Deacetylbaccine III is the fifth intermediate of paclitaxel biosynthesis. The biosynthetic pathway consists of approximately 20 enzymatic steps but is not fully elucidated. 10-Deacetylbaccine III is an antineoplastic agent and an anti-cancer intermediate.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cancer

[References]

[1]. Li S, Zhang P, Zhang M, Fu C, Yu L. Functional analysis of a WRKY transcription factor involved in transcriptional activation of the DBAT gene in Taxus chinensis. Plant Biol (Stuttg). 2013 Jan;15(1):19-26.

[2]. Naill MC, Kolewe ME, Roberts SC. Paclitaxel uptake and transport in Taxus cell suspension cultures. Biochem Eng J. 2012 Apr 15;63:50-56.

[3]. Qayum M, Nisar M, Shah MR, et al. Analgesic and antiinflammatory activities of taxoids from Taxus wallichiana Zucc. Phytother Res. 2012 Apr;26(4):552-6.

[4]. Kevin Walker and Rodney Croteau. Taxol biosynthesis: Molecular cloning of a benzoyl- CoA:taxane 2α-O-benzoyltransferase cDNA from Taxus and functional expression in Escherichia coli. PNAS, 2000 , 97（25）：13591-13596.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
716.8±60.0 °C at 760 mmHg

[ Melting Point ]:
231-236 °C

[ Molecular Formula ]:
C₂₉H₃₆O₁₀

[ Molecular Weight ]:
544.590

[ Flash Point ]:
233.5±26.4 °C

[ Exact Mass ]:
544.230835

[ PSA ]:
159.82000

[ LogP ]:
3.51

[ Vapour Pressure ]:
0.0±2.4 mmHg at 25°C

[ Index of Refraction ]:
1.624

[ Water Solubility ]:
INSOLUBLE

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
T:Toxic

[ Risk Phrases ]:
R23/24/25

[ Safety Phrases ]:
S45-S38-S36/37/39-S28A

[ RIDADR ]:
1544

[ WGK Germany ]:
3

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Disposition of [G-(3)H]paclitaxel and cremophor EL in a patient with severely impaired renal function.

Drug Metab. Dispos. 27 , 1300, (1999)

In the present work, we studied the pharmacokinetics and metabolic disposition of [G-(3)H]paclitaxel in a female patient with recurrent ovarian cancer and severe renal impairment (creatinine clearance...

Molecular mechanisms of patupilone resistance.

Cancer Res. 68 , 10197-10204, (2008)

Patupilone is an epothilone in advanced clinical development that has shown promising efficacy in heavily pretreated patients. This study aimed at characterizing the mechanisms of patupilone activity ...

Taxol biosynthesis: Molecular cloning of a benzoyl- CoA:taxane 2-O-benzoyltransferase cDNA from Taxus and functional expression in Escherichia coli Kevin Walker and Rodney Croteau PNAS

Proc. 10th Am. Peptide Symp 97 , 13591-13596, (2000)