TAXOL - (33069-62-4)

introduzione

Nome: 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
Numero CAS: 33069-62-4
Formula chimica: C47H51NO14
Massa molare: 853.90614 g
Percentuale di massa: C 66.108 %; H 6.0199 %; N 1.6403 %; O 26.231 % 

Classificazione

• biologico • aromatico • estere • chetone

Usi / Funzione

• "...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

Proprietà fisiche

Punto di fusione:*
214°C †3 = 487.15 K = 417.2°F


* - 1 atm pressure
† - decompone

bonding

doppi legami: 15
tripli legami: 0
Sigma Bonds: 119
pi Bonds: 15
Totale: 134
carboxyl Gruppi: 0
gruppi idrossilici: 3

Per maggiori informazioni

Wikipedia
riviste:
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)

fonti

(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.