TAXOL - (33069-62-4)

Einführung

Name: Taxol; paclitaxel; (2α,4α,5β,7β,10β,13α)-4,10-bis(acetyloxy)-13-{[(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]oxy}-1,7-dihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate
* IUPAC
CAS-Nummer: 33069-62-4
Chemische Formel: C47H51NO14
Molmasse: 853.90614 g
Massenprozent: C 66.108 %; H 6.0199 %; N 1.6403 %; O 26.231 % 

Einstufung

• organisch • aromatisch • Ester • Keton

Verwendung / Funktion

• "...has a significant activity against several forms of cancer, especially ovarian cancer...Some anticancer drugs kill cancerous cells without acting on DNA. Certain alkaloids, such as vincristine, and taxol, kill dividing cells by preventing the formation of cellular microstructures needed for division." 1

• "Tool in study of structure and function of microtubules. Antineoplastic." 2

Physikalische Eigenschaften

Schmelzpunkt:*
214°C †3 = 487.15 K = 417.2°F


* - 1 atm pressure
† - zersetzt

Kleben

Doppelbindungen: 15
Dreifachbindungen: 0
Sigma Bonds: 119
Pi Bonds: 15
Gesamt: 134
Carboxygruppen: 0
HYDROXYLGRUPPEN: 3

Für mehr Informationen

Wikipedia
Zeitschriften:
M. C. Wani et. al., J. Am. Chem. Soc. 93, 2325 (1971)
P. B. Schiff et. al., Nature 277, 665 (1979)
G. Chauviere et. al., C.R. Acad. Sci. Paris Ser. II 293, 501 (1981)
R. A. Holton et. al., J. Am. Chem. Soc. 110, 6558 (1988)
K. C. Nicolaou et. al., Nature 367, 630 (1994)
A. Stierle et. al., Science 260, 241 (1993)
M. W. Saville et. al., Lancet 346, 26 (1995)
J. J. Manfredi, S. B. Horwitz, Pharmacol. Ther. 25, 83-125 (1984)
S. B. Horwitz et. al., Ann. N.Y. Acad. Sci. 466, 733-744 (1986)
S. B. Horwitz, Trends Pharmacol. Sci. 13, 134-136 (1992)
C. D. Runowicz et. al., Cancer 71, 1591-1596 (1993)

Quellen

(1) - Suchocki, John. Conceptual Chemistry: Understanding Our World of Atoms and Molecules; Addison Wesley: San Francisco, California, 2001; pp 441, 450.
(2) - The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 13th ed.; Budavari, S.; O'Neil, M.J.; Smith, A.; Heckelman, P. E.; Kinneary, J. F., Eds.; Merck & Co.: Whitehouse Station, NJ, 2001; entry 7052.
(3) - Lide, David R. CRC Handbook of Chemistry and Physics, 84th ed.; CRC Press: Boca Raton, FL, 2003; p 3-508.