CAS REGISTRY #:

• 33069-62-4

GENERIC CLASS:

• Diterpenes/Taxanes/Anti-neoplastic agents

NAMES:

• Paclitaxel;
• Taxol®. (Registered Trademark);
• Benzenepropanoic acid, .beta.-(benzoylamino)- .alpha.-hydroxy-, 6,12b-bis(acetyl oxy)-12-(benzoyloxy)- 2a,3, 4,4a,5,6,9,10,11,12,12a,12b,-dodecahydro-4,11- dihydroxy-4a,8, 13,13-tetramethyl-5-oxo- 7,11-methano- 1H-cyclodeca[3,4]benz[1, 2-b]oxet-9-yl ester, [2aR-[2a.alpha.,4.beta.,4a.beta.,6.beta., 9.alpha.(alpha. R*,.beta.S*),11.alpha.,12.alpha.,12a.alpha., 12b.alpha.]]- (9CI);
• Tax-11-en-9-one, 5.beta.,20-epoxy-1,2.alpha.,4,7.beta., 10.beta.,13.alpha.- hexahydroxy-, 4,10-diacetate 2- benzoate, 13-ester with(2R,3S)-N-benzoyl-3-phenylisoserine (8CI);
• 7,11-Methano-5H-cyclodeca[3,4]benz[1,2-b]oxete, benzenepropanoic acid deriv. (9CI);

IUPAC SYSTEMATIC NAME:

• [2aR-[2a,4,4a,6,9(R*,S*),11,12,12a,12b]]- -(Benzoylamino)- -hydroxybenzenepropanoic acid 6,12b-bis (acetyloxy)-12-(benzoyloxy)-2a, 3, 4, 4a, 5, 6, 9, 10, 11, 12, 12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester.

MOLECULAR FORMULA:

• C₄₇H₅₁NO₁₄

MOLECULAR STRUCTURE:

• Please see Figure 1 (above)

MOLECULAR WEIGHT:

• 853.92 g/mol

% COMPOSITION:

• C 66.11%, H 6.02%, N 1.64%, O 26.23%

MELTING POINT:

• 213-216 ^oC

SPECIFIC ROTATION (MeOH):

• [ ]20D -49^o

TLC (silica, 50% EtOAc in hexanes):

• Rf=0.125

UV MAX (MeOH):

• 227, 273 nm ( 29800, 1700)

IR (in Nujol):

• u_max: 3300-3500 (OH & NH) , 1730 (ester) , 1710 (ketone) , 1650 (amide) cm^-1

1HNMR (500.13 MHz, in deuterated methylene chloride):

H on	d (ppm)	(coupling between hydrogens): J (in Hz)
C2	5.65	[(2,3): 7] ; [(2,14a): <0.7]
C3	3.80	[(3,2): 7] ; [(3,20a): ª0.7]
C5	4.96	[(5,6a): 9.6] ; [(5,6b): 2.5] ; [(5,20b): 1.1]
C6	2.52	[(6a,6b): 15] ; [(6a,7): 6.8] ; [(6a,5): 9.6]
C6	1.80	[(6b,6a): 15] ; [(6b,7): 11] ; [(6b,5): 2.5]
C7	4.42	[(7,6a): 6.8] ; [(7,6b): 11] ; [(7,7-OH): <0.7]
C7-OH	2.43*	[(7-OH,7): <0.7]
C10	6.26	s
C13	6.23	[(13,14a): 8.8] ; [(13,14a): 8.8] ; [(13,18): 1.5]
C14	2.37	[(14a,14b): 16] ; [(14a,13): 8.8]
C14	2.27	[(14b,2): ª0.7] ; [(14b,14a): 16] ; [(14b,13): 8.8]
C16	1.23	s (4J coupling to C17-H is observed in the 2QF-COSY)
C17	1.12	s (4J coupling to C16-H is observed in the 2QF-COSY)
C18	1.83	[(18,13): 1.5]
C19	1.63	s (4J coupling to C3-H is observed in the 2QF-COSY)
C20	4.28	[(20a,20b): 8.8] ; [(20a,3): ª0.7]
C20	4.16	[(20b,20a): 8.8] ; [(20b,5): 1.1]
C2'	4.80	[(2',3'): 2.6] ; [(2',2'OH): 2.0]
C3'	5.78	[(3',2'): 2.6] ; [(3',N3'): 8.8] ; [(3',C3'-Ph(o)): <0.7]
N3'	7.00	[(N3',3'): 8.8]
C2'-OH	3.55	[(2'OH,2'): 8.8]
C4-OAc	2.40	s
C10-OAc	2.22	s
C2-OCO-Ph	8.15(o); 7.54(m); 7.63(p)
C3'-Ph	7.49(o); 7.43(m); 7.36(p)
N3'-CO-Ph	7.75(o); 7.41(m); 7.51(p)	..........* = observed only in the 2QF-COSY ..........s = singlet ; [ o = orthro ; m = meta ; p = para (positions)]

MASS SPECTROMETRY:

• m/e=854.3360
• M + H⁺ calculated for C₄₇H₅₁NO₁₄=854.3388

The Dictionary of Organic Compounds. ( T-0.00030)

Dictionary of Natural products (T-00153)

J.Amer.Chem.Soc. 1971, 93 ,pp 2325

Structure of taxol from : Tetrahedron Lett. Vol.33 , No.9 ,pp 1169- 1172, 1992

NMR spectra taken by J.Ojima et al.

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