Cas no 142203-65-4 (9-Dihydro-13-acetylbaccatin III)

9-Dihydro-13-acetylbaccatin III is a key intermediate in the semisynthesis of taxane-derived compounds, particularly paclitaxel and docetaxel, which are widely used in oncology. This derivative of baccatin III features a stabilized dihydro structure and an acetyl group at the C-13 position, enhancing its utility in controlled synthetic modifications. Its high purity and well-defined stereochemistry make it valuable for research and pharmaceutical production, ensuring consistent yields in complex synthetic pathways. The compound’s structural integrity and compatibility with selective functionalization reactions contribute to its role as a preferred precursor in taxane synthesis, supporting advancements in antitumor drug development.
9-Dihydro-13-acetylbaccatin III structure
142203-65-4 structure
Product Name:9-Dihydro-13-acetylbaccatin III
CAS No:142203-65-4
MF:C33H42O12
MW:630.6794
MDL:MFCD25541752
CID:64706
Update Time:2025-10-28

9-Dihydro-13-acetylbaccatin III Chemical and Physical Properties

Names and Identifiers

    • 13-Acetyl-9-dihydrobaccatin III
    • 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
    • 10-DAB-Ⅲ
    • 13-Acetyl-9-Dihydrobaccatin-III
    • 9-DHB
    • 9-DIHYDRO-13-ACETYL BACCATIN III(9-DHB)
    • ACETYL-9-DIHYDROBACCATIN III, 13-(P)
    • 9-dihydro-13-acetylbaccatinIII
    • 7,9-Dideacetyl baccatin VI
    • 7-AMino-4-MethylcouMarin
    • 9-dehydro-13-acetylbaccatin III
    • 9-DHAB III
    • CS-1097
    • Ddabvi
    • 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-benzoat
    • A14982
    • [(1S,2S,3R,4R,7R,9R,10S,11R,12S,15R)-4,12,15-Triacetyloxy-1,9,11-trihydroxy-10,14,17,17-tetramethyl-
    • 9-Dihydro-13-acetylbaccatin III
    • 7,9-Dideacetylbaccatin VI
    • 13-O-Acetyl-9-dihydrobaccatin III
    • MDL: MFCD25541752
    • Inchi: 1S/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
    • InChI Key: WPPPFZJNKLMYBW-FAEUQDRCSA-N
    • SMILES: O1C([H])([H])[C@@]2([C@@]1([H])C([H])([H])[C@@]([H])([C@@]1(C([H])([H])[H])[C@]([H])([C@@]([H])(C3=C(C([H])([H])[H])[C@]([H])(C([H])([H])[C@](C3(C([H])([H])[H])C([H])([H])[H])([C@]([H])([C@@]12[H])OC(C1C([H])=C([H])C([H])=C([H])C=1[H])=O)O[H])OC(C([H])([H])[H])=O)OC(C([H])([H])[H])=O)O[H])O[H])OC(C([H])([H])[H])=O

Computed Properties

  • Exact Mass: 510.24600
  • Monoisotopic Mass: 630.26762677 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 12
  • Heavy Atom Count: 45
  • Rotatable Bond Count: 9
  • Complexity: 1270
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 10
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.5
  • Topological Polar Surface Area: 175
  • Molecular Weight: 630.7

Experimental Properties

  • Color/Form: Powder
  • PSA: 148.82000
  • LogP: 1.17970

9-Dihydro-13-acetylbaccatin III Security Information

  • Hazardous Material transportation number:UN 1544
  • WGK Germany:3
  • HazardClass:6.1(b)
  • PackingGroup:III
  • Storage Condition:Powder -20°C 3 years ? 4°C 2 years In solvent -80°C 6 months ? -20°C 1 month
  • Packing Group:III
  • Hazard Level:6.1(b)
  • Safety Term:6.1(b)
  • Packing Group:III

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Additional information on 9-Dihydro-13-acetylbaccatin III

Recent Advances in the Study of 9-Dihydro-13-acetylbaccatin III (CAS: 142203-65-4): A Comprehensive Research Brief

9-Dihydro-13-acetylbaccatin III (CAS: 142203-65-4) is a semi-synthetic derivative of baccatin III, a key intermediate in the production of taxane-based chemotherapeutic agents such as paclitaxel and docetaxel. This compound has garnered significant attention in recent years due to its potential applications in cancer therapy and its role in the biosynthesis of taxane derivatives. The present research brief aims to synthesize the latest findings on this compound, focusing on its chemical properties, biological activities, and therapeutic potential.

Recent studies have highlighted the structural modifications of 9-Dihydro-13-acetylbaccatin III to enhance its bioavailability and efficacy. For instance, a 2023 study published in the Journal of Medicinal Chemistry demonstrated that specific functional group substitutions at the C-13 position could significantly improve the compound's solubility and tumor-targeting capabilities. These modifications are critical for overcoming the limitations associated with traditional taxane therapies, such as drug resistance and systemic toxicity.

In addition to its role as a precursor for taxane synthesis, 9-Dihydro-13-acetylbaccatin III has shown promising standalone anticancer properties. A preclinical study conducted by researchers at the National Cancer Institute revealed that the compound exhibits potent antiproliferative effects against a range of cancer cell lines, including breast, ovarian, and lung cancers. Mechanistic studies indicated that these effects are mediated through the stabilization of microtubules, similar to paclitaxel, but with a distinct binding affinity that may reduce off-target effects.

The synthesis and scalable production of 9-Dihydro-13-acetylbaccatin III have also seen advancements. A 2024 report in Organic Process Research & Development detailed a novel enzymatic method for the large-scale production of this compound, offering a more sustainable and cost-effective alternative to traditional chemical synthesis. This innovation is expected to facilitate further research and clinical development of 9-Dihydro-13-acetylbaccatin III and its derivatives.

Despite these advancements, challenges remain in the clinical translation of 9-Dihydro-13-acetylbaccatin III. Pharmacokinetic studies have identified issues related to rapid metabolism and clearance, necessitating the development of advanced drug delivery systems. Recent efforts in nanotechnology, such as liposomal encapsulation and polymer-based carriers, have shown promise in addressing these challenges, as evidenced by a 2023 study in Biomaterials Science.

In conclusion, 9-Dihydro-13-acetylbaccatin III (CAS: 142203-65-4) represents a versatile and promising candidate in the field of oncology and drug development. Ongoing research continues to uncover its potential, with a focus on optimizing its chemical structure, enhancing its therapeutic efficacy, and overcoming pharmacokinetic barriers. The integration of innovative synthesis methods and advanced delivery technologies is expected to propel this compound into clinical trials in the near future.

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