CAS 152044-53-6

Epothilone A

Description:

Epothilone A is a natural product and a member of the epothilone family, which are macrocyclic compounds known for their potent antitumor activity. It is derived from the myxobacterium Sorangium cellulosum and exhibits a structure that includes a 16-membered macrolide ring. Epothilone A functions primarily as a microtubule stabilizer, similar to taxanes, by binding to the β-tubulin subunit of microtubules, thereby inhibiting their depolymerization and disrupting normal mitotic processes in cancer cells. This mechanism makes it a candidate for cancer therapy, particularly in cases resistant to conventional treatments. The compound is characterized by its relatively high solubility in organic solvents and moderate stability under physiological conditions. Its pharmacological profile includes significant cytotoxicity against various cancer cell lines, making it a subject of interest in drug development. However, like many natural products, its clinical application may be limited by factors such as bioavailability and the complexity of synthesis. Overall, Epothilone A represents a promising avenue in the search for effective anticancer agents.

Formula: C₂₆H₃₉NO₆S

InChI: InChI=1S/C26H39NO6S/c1-14-8-7-9-19-21(32-19)11-20(15(2)10-18-13-34-17(4)27-18)33-23(29)12-22(28)26(5,6)25(31)16(3)24(14)30/h10,13-14,16,19-22,24,28,30H,7-9,11-12H2,1-6H3/b15-10+/t14-,16+,19+,20-,21-,22-,24-/m0/s1

InChI key: InChIKey=HESCAJZNRMSMJG-KKQRBIROSA-N

SMILES: C(=C\C=1N=C(C)SC1)(\C)/[C@@H]2C[C@]3([C@](O3)(CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O2)[H])[H]

Synonyms:

• (1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12-tetramethyl-3-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
• (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12-tetramethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
• 4,17-Dioxabicyclo14.1.0heptadecane-5,9-dione, 7,11-dihydroxy-8,8,10,12-tetramethyl-3-(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl-, (1S,3S,7S,10R,11S,12S,16R)-
• 4,17-Dioxabicyclo[14.1.0]heptadecane-5,9-dione, 7,11-dihydroxy-8,8,10,12-tetramethyl-3-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (1S,3S,7S,10R,11S,12S,16R)-
• 4,17-Dioxabicyclo[14.1.0]heptadecane-5,9-dione, 7,11-dihydroxy-8,8,10,12-tetramethyl-3-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, [1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]-
• Epo A
• Epothilone A
• Epothilone A
• (-)-Epothilone A

Epothilone A

CAS: 152044-53-6

Formula: C₂₆H₃₉NO₆S

Purity: 98%

Color and Shape: Solid

Molecular weight: 493.6560

Ref: IN-DA006UJV

Ixabepilone Impurity 5 (Epothilone A)

CAS: 152044-53-6

Formula: C₂₆H₃₉NO₆S

Color and Shape: Off-White Solid

Molecular weight: 493.67

Ref: 4Z-I-069006

(1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12-Tetramethyl-3-((E)-1-(2-Methylthiazol-4-Yl)Prop-1-En-2-Yl)-4,17-Dioxabicyclo[14.1.0]Heptadecane-5,9-Dione

CAS: 152044-53-6

(1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12-Tetramethyl-3-((E)-1-(2-Methylthiazol-4-Yl)Prop-1-En-2-Yl)-4,17-Dioxabicyclo[14.1.0]Heptadecane-5,9-Dione

Purity: 98%

Molecular weight: 493.66g/mol

Ref: 54-OR1023194

Epothilone A

CAS: 152044-53-6

Epothilone A

Purity: ≥98%

Molecular weight: 493.66g/mol

Ref: 54-BUP13471

(-)-Epothilone A

CAS: 152044-53-6

Formula: C₂₆H₃₉NO₆S

Molecular weight: 493.66

Ref: 7W-GK4811

Epothilone A

CAS: 152044-53-6

Epothilone A (Epo A) is a microtubule-stabilizing agent with EC0.01 of 2 μM.

Formula: C₂₆H₃₉NO₆S

Purity: 99.89% - 99.92%

Color and Shape: Solid

Molecular weight: 493.66

Ref: TM-T6490

Epothilone A

Controlled Product

CAS: 152044-53-6

Applications The epothilones are a novel class of antineoplastic agents possessing antitubulin activity. Epothilone A, B isolated from Sorangium cellulosum was associated with cell cycle arrest at G2/M transition and apoptosis that was resisted with overexpression of β-tubulin and P-glycoprotein in human bladder carcinoma cell.
References Bollag, D.M., et al.: Cancer. Res., 55, 2325 (1995), Hardt, I.H., et al.: J. Nat. Prod., 64, 847 (2001), Gerth, K., et al.: J. Antibiot., 55, 41, 45 (2002)

Formula: C₂₆H₃₉NO₆S

Color and Shape: Neat

Molecular weight: 493.66

Ref: TR-E588980