Epothilone D (synthetic)

CAS No.: 189453-10-9   Request for quotation

Epothilone D (Epo-D) is a paclitaxel-like microtubule-stabilizing agent that was isolated from the myxobacterium Sorangium cellulosum. Although epothilone D can inhibit proliferation in multiple tumor cell lines, the effect of epothilone D on neointimal hyperplasia after angioplasty has not been reported. Some experiment result that epothilone D may regulate the cell cycle G1-checkpoint proteins as its major molecular mechanism for inhibiting neointimal hyperplasia after in vivo rat carotid artery injury.[1]

The 9-(S)-Epo D and 9-(R)-Epo D demonstrated significant difference in inhibition activities against cancer cell lines and in conformational analysis.[2]

The ring-opening or ring fragmentation reactions of cyclopropanol intermediates are used in the total synthesis of epothilone D for the creation of trisubstituted double bonds, an ethyl ketone functionality, as well as for the protection of carboxylic and ester groups. Epothilone D is obtained in 1.6% overall yield (24 steps in the longest linear sequence) starting from (R)-methyl 2,3-O-isopropylideneglycerate. The key cyclopropanol intermediates are efficiently obtained by titanium(IV)-catalyzed reactions of readily available esters with Grignard reagents.[4]

Epothilone D Specification

Appearance White Crystalline powder   Standard Packing 50mg/bag or per customer request
Purity (HPLC) ≥ 98%   Inventory Normally we have Epothilone D in stock
Melting Point: 63 - 66 °    
      Epothilone D physical parameters
      CAS No: 189453-10-9
      Formula C27H41NO5S
      Molecular Weight 491.68
      Synonym (4S,7R,8S,9S,13Z,16S)-4,8-Dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]oxacyclohexadec-13-ene-2,6-dione; (-)-Desoxyepothilone B; (-)-Epothilone D; 12,13-Deoxyepothilone B; 12,13-Desoxyepothilone B; Desoxyepothilone B; Epo D; Epothilone D; KOS 862; NSC 703147;
      Solubility  
      Structure Epothilone D(synthetic)
       
       
       
         
Certificate of Analysis Epothilone D COA  
Literature Epothilone D literature  
MSDS Epothilone D MSDS  
         
References:  
1. Tack-Joong Kim et al: Vascular Pharmacology, 47(4) 2007, 229-237 "Epothilone D, a microtubule-stabilizing compound, inhibits neointimal hyperplasia after rat carotid artery injury by cell cycle arrest via regulation of G1-checkpoint proteins"
2. Feng Sang et al: European Journal of Medicinal Chemistry, 68 (2013) 321-332 "Epothilone D and its 9-Methyl analogues: Combinatorial syntheses, conformation, and biological activities"
3 Robert L. Broadrup et al: Bioorganic Chemistry, 33(2) 2005 116–133. "Total synthesis of 12,13-desoxyepothilone B (Epothilone D)"
4. Alaksiej L.Hurski et al: Tetrahedron Letters 51(27) 2010,3497–3500 "Total synthesis of epothilone D by sixfold ring cleavage of cyclopropanol intermediates."
 
 
 

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Epothilone D