142203-65-4

Basic information

• Product Name: 13-Acetyl-9-dihydrobaccatin III
• Synonyms: 2a,3,4,4a,5,6,9,10,12,12a-Decahydro-4a,8,13,13-tetramethyl-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxete-4,5,6,9,11,12,12b-heptol (2aR,4S,4aS,5R,6R,9S,11S,12S,12aR,12bS)-6,9,12b-triacetate 12-benzoate;9-DIHYDRO-13-ACETYL BACCATIN(9-DHB);7,9-Dideacetylbaccatin VI;19-DHB;9-DIHYDRO-13-ACETYL BACCATIN III(9-DHB);13-Acetyl-9-dihydrobaccatin III;9-Dihydro-13-acetylbaccatinIII from Taxus canadensis;9-Dihydro-13-acetyl baccatinⅢ(9-DHB)
• CAS NO: 142203-65-4
• Molecular Formula: C₃₃H₄₂O₁₂
• Molecular Weight: 630.67938
• Product Categories: Miscellaneous Natural Products
• Mol File: 142203-65-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 704.541 °C at 760 mmHg
• Flash Point: 217.569 °C
• Appearance: /
• Density: 1.366 g/cm³
• Vapor Pressure: 7.81E-21mmHg at 25°C
• Refractive Index: 1.594
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 12.61±0.70(Predicted)
• CAS DataBase Reference: 13-Acetyl-9-dihydrobaccatin III(CAS DataBase Reference)
• NIST Chemistry Reference: 13-Acetyl-9-dihydrobaccatin III(142203-65-4)
• EPA Substance Registry System: 13-Acetyl-9-dihydrobaccatin III(142203-65-4)

Safety Data

• RIDADR: 1544
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 142203-65-4(Hazardous Substances Data)

Usage

Description

13-Acetyl-9-dihydrobaccatin III is a taxane compound originally isolated from the plant T. canadensis. It is characterized by its ability to inhibit the proliferation of P388 leukemia cells with an IC50 value of 20 μg/ml, making it a promising candidate for pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
13-Acetyl-9-dihydrobaccatin III is used as an apoptosis inducer for its potential role in cancer treatment. It has demonstrated the ability to induce cell death in cancer cells, which can be a valuable asset in the development of anticancer drugs.
Additionally, due to its taxane nature, 13-Acetyl-9-dihydrobaccatin III may also be used as a precursor in the semisynthesis of other taxane-based anticancer drugs, such as paclitaxel and docetaxel, which are widely used in the treatment of various types of cancer.

InChI:InChI=1/C33H42O12/c1-16-21(42-17(2)34)14-33(40)28(44-29(39)20-11-9-8-10-12-20)26-31(7,22(37)13-23-32(26,15-41-23)45-19(4)36)27(38)25(43-18(3)35)24(16)30(33,5)6/h8-12,21-23,25-28,37-38,40H,13-15H2,1-7H3/t21-,22-,23+,25+,26-,27-,28-,31+,32-,33+/m0/s1

Downstream Products

• 162743-81-9 13-acetyl-9(R)-dihydrobaccatin III 7,9-thionocarbonate 
• 154854-30-5 C₃₃H₄₀O₁₁ 
• 148584-49-0 9(R)-dihydro-7,9-isopropylidene-13-acetylbaccatin-III 
• 159012-45-0 C₃₅H₄₄O₁₂S₂ 
• 162489-62-5 10-deacetyl-9-dihydro-13-acetylbaccatin III 
• 156168-98-8 7,9,13-trideacetylbaccatin VI 
• 57672-79-4 baccatine VI 
• 247244-56-0 7-triethylsilyl-9-dihydro-13-acetylbaccatin III 
• 290815-45-1 7-triisopropylsilyl-9-dihydro-13-acetylbaccatin III 

Relevant articles and documents

CONVERSION 9-DIHYDRO-13-ACETYLBACCATIN III TO 10-DEACETYLBACCATIN III

The present invention relates to a process is provided for the conversion of 9-dihydro-13-acetylbaccatin to 10-deacetylbaccatin III. The process includes four specific interrelated steps. The first step involves protecting the 7-hydroxyl group of 9-dihydro-13-acetylbaccatin and converting that 7-hydroxyl-protected 9-dihydro-13-acetylbaccatin to 7, 13-diacetyl-9-dihydrobaccatin III. The second step involves reacting that 7, 13-diacetyl-9-dihydrobaccatin III with 4-methylmorpholine N-oxide in a suitable solvent and oxidizing that reaction product to yield 7, 13-diacetylbaccatin. The third step involves deacetylating that 7, 13-diacetyl-9-dihydrobaccatin III to yield 7-acetylbaccatin III. The fourth and final step involves converting that 7-acetylbaccatin III to 10-deacetylbaccatin III.