Introduction
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 Number: 33069-62-4
Molar Mass: 853.90614 g
Mass Percent: C 66.108 %; H 6.0199 %; N 1.6403 %; O 26.231 %
Classification
Uses/Function
• "...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
Physical Properties
Melting Point:*
214°C †3 = 487.15 K = 417.2°F
* - 1 atm pressure
† - decomposes
Bonding
Double Bonds: 15
Triple Bonds: 0
Sigma Bonds: 119
Pi Bonds: 15
Total: 134
Carboxyl Groups: 0
Hydroxyl Groups: 3
For More Information
Wikipedia
Journals:
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)
Sources
(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.