Product Name

  • Name

    Paclitaxel

  • EINECS 205-285-7
  • CAS No. 33069-62-4
  • Article Data81
  • CAS DataBase
  • Density 1.39 g/cm3
  • Solubility solubile in methanol: 50 mg/mL, clear, colorless
  • Melting Point 213 °C
  • Formula C47H51NO14
  • Boiling Point 957.115 °C at 760 mmHg
  • Molecular Weight 853.92
  • Flash Point 532.644 °C
  • Transport Information
  • Appearance white powder
  • Safety 22-26-36/37/39-45
  • Risk Codes 37/38-41-42/43-62-68-40-48-20/21/22
  • Molecular Structure Molecular Structure of 33069-62-4 (Paclitaxel)
  • Hazard Symbols R40:; R41:;
  • Synonyms BMS 181339-01;Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, 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, (2aR-(2a-alpha,4-beta,4a-beta,6-beta,9-alpha(alpha-R*,beta-S*),11-alpha,12-alpha,12a-alpha, 12b-alpha))-;Taxol.RTM. (Registered Trademark);QW 8184;MBT 0206;12-benzoate, 9-ester with (2R,3S)-N-benzoyl-3-phenylisoserine;Palcitaxel;Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, 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, (2aR-(2aalpha,4beta,4abeta,6beta,9alpha(alphaR*,betaS*),11alpha,12alpha,12aalpha,12balpha))-;Prestwick_459;Abraxane;Taxol (TN);Paxceed;NSC-125973;Paxene;Plaxicel;Onxol;Indirubin;Paclitaxle;Paclitaxel Semi-Synthetic USP30;
  • PSA 221.29000
  • LogP 4.12660

Synthetic route

1-hydroxy-7β-triethylsilyloxy-9-oxo-10β-acetyloxy-5β,20-epoxytax-11-ene-2α,4,13α-triyl 4-acetate 2-benzoate 13-[(2R,3S)-3-benzoylamino-2-triethylsilyloxy-3-phenylpropanoate]
135365-62-7

1-hydroxy-7β-triethylsilyloxy-9-oxo-10β-acetyloxy-5β,20-epoxytax-11-ene-2α,4,13α-triyl 4-acetate 2-benzoate 13-[(2R,3S)-3-benzoylamino-2-triethylsilyloxy-3-phenylpropanoate]

taxol
33069-62-4

taxol

Conditions
ConditionsYield
With pyridine; hydrogen fluoride In water; acetonitrile at 0 - 25℃; for 14h;98%
With pyridine; hydrogen fluoride In water; acetonitrile at 0 - 25℃; for 14h;98%
With hydrogenchloride In methanol; water at -5 - 30℃; for 27h;90%
With pyridine hydrogenfluoride In tetrahydrofuran at 25℃; for 1.25h;80%
Reaxys ID: 15738630

Reaxys ID: 15738630

benzoyl chloride
98-88-4

benzoyl chloride

taxol
33069-62-4

taxol

Conditions
ConditionsYield
Stage #1: With dmap; chloro-trimethyl-silane; diisopropylamine In tetrahydrofuran at 20℃; for 1h;
Stage #2: Schwartz's reagent In tetrahydrofuran at 0℃; for 4h;
Stage #3: benzoyl chloride With tert-butyl methyl ether; N,N-bis-(2-hydroxyethyl)glycine; sulfuric acid; sodium hydrogencarbonate more than 3 stages;		86.6%
Reaxys ID: 15738631

Reaxys ID: 15738631

benzoyl chloride
98-88-4

benzoyl chloride

taxol
33069-62-4

taxol

Conditions
ConditionsYield
With tert-butyl methyl ether; N,N-bis-(2-hydroxyethyl)glycine; sulfuric acid; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; triethylamine; ethyl vinyl ether; Schwartz's reagent In tetrahydrofuran; water; ethyl acetate at 5 - 20℃; for 24.8333h;80%
Reaxys ID: 15738641

Reaxys ID: 15738641

benzoyl chloride
98-88-4

benzoyl chloride

taxol
33069-62-4

taxol

Conditions
ConditionsYield
Stage #1: With dmap; chloro-trimethyl-silane; diisopropylamine In tetrahydrofuran at 0℃; for 1h;
Stage #2: Schwartz's reagent In tetrahydrofuran at 5℃; for 4h;
Stage #3: benzoyl chloride With tert-butyl methyl ether; N,N-bis-(2-hydroxyethyl)glycine; sulfuric acid; sodium chloride more than 3 stages;		76.5%
(2'R,3'S)-2'-ethoxyethyl-7-triethylsilyl taxol
439813-57-7

(2'R,3'S)-2'-ethoxyethyl-7-triethylsilyl taxol

taxol
33069-62-4

taxol

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 0℃; for 30h;90%
With hydrogenchloride In ethanol at 0℃; for 72h;80%
(2'R,3"S)-2'-(2-methoxy-2-propyloxy)-7-triethylsilyl taxol

(2'R,3"S)-2'-(2-methoxy-2-propyloxy)-7-triethylsilyl taxol

taxol
33069-62-4

taxol

Conditions
ConditionsYield
With pyridine; hydrogen fluoride In water; acetonitrile at 0 - 25℃; for 18h;99%
Stage #1: (2'R,3"S)-2'-(2-methoxy-2-propyloxy)-7-triethylsilyl taxol With trifluoroacetic acid In water; acetic acid at 20℃; for 7h;
Stage #2: With sodium acetate In dichloromethane; water; acetic acid for 0.25h;		26.3 g
Reaxys ID: 15738633

Reaxys ID: 15738633

benzoyl chloride
98-88-4

benzoyl chloride

taxol
33069-62-4

taxol

Conditions
ConditionsYield
With tert-butyl methyl ether; N,N-bis-(2-hydroxyethyl)glycine; sulfuric acid; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; triethylamine; ethyl vinyl ether; Schwartz's reagent In tetrahydrofuran; water; ethyl acetate at -5 - 20℃; for 26.8333h;43.6%
Stage #1: Schwartz's reagent In tetrahydrofuran at 5℃; for 4h;
Stage #2: With N,N-bis-(2-hydroxyethyl)glycine In tetrahydrofuran; ethyl acetate for 0.833333h;
Stage #3: benzoyl chloride With tert-butyl methyl ether; sulfuric acid; sodium hydrogencarbonate more than 3 stages;
7-(triethylsilyl)-13-O-[((4S,5R)-2,4-diphenyl-4,5-dihydrooxazol-5-yl)carbonyl]baccatin
158722-23-7

7-(triethylsilyl)-13-O-[((4S,5R)-2,4-diphenyl-4,5-dihydrooxazol-5-yl)carbonyl]baccatin

taxol
33069-62-4

taxol

Conditions
ConditionsYield
With hydrogenchloride In methanol at 60 - 80℃; for 3.5h;80%
With hydrogenchloride In methanol76%
With hydrogenchloride at 95℃; for 2h;75%
With hydrogenchloride In methanol at 60℃; for 3h; Hydrolysis;
dmap
1122-58-3

dmap

taxol
33069-62-4

taxol

Conditions
ConditionsYield
With hydrogenchloride; water In ethanol at 0 - 20℃; for 2.41667h;100%
C50H59NO14Si

C50H59NO14Si

taxol
33069-62-4

taxol

Conditions
ConditionsYield
With hydrogenchloride In water at 20℃;93.3%
7-O-(2-chloroacetyl)paclitaxel
162081-12-1

7-O-(2-chloroacetyl)paclitaxel

taxol
33069-62-4

taxol

Conditions
ConditionsYield
With ammonia In pyridine at 0 - 5℃; for 12h;84%
13-O-[[(4S,5R)-3-N-benzoyl-4-phenyloxazolidin-2RS-methoxy-5-yl]carbonyl]-7-O-triethylsilylbaccatin III
906370-55-6

13-O-[[(4S,5R)-3-N-benzoyl-4-phenyloxazolidin-2RS-methoxy-5-yl]carbonyl]-7-O-triethylsilylbaccatin III

taxol
33069-62-4

taxol

Conditions
ConditionsYield
With hydrogenchloride; water In ethanol; ethyl acetate at 45℃; for 4h;80%
C61H71NO15Si

C61H71NO15Si

taxol
33069-62-4

taxol

Conditions
ConditionsYield
With acetic acid; trifluoroacetic acid In water at 30℃; Temperature; Concentration;81%
7-O-(triethylsilyl)paclitaxel
148930-55-6

7-O-(triethylsilyl)paclitaxel

taxol
33069-62-4

taxol

Conditions
ConditionsYield
With pyridine hydrogenfluoride In tetrahydrofuran Ambient temperature;100%
With hydrogenchloride; water In ethanol at 20℃; for 2h; Hydrolysis;100%
With hydrogenchloride In ethanol; water at 0 - 20℃; for 2.41667h;100%
Multi-step reaction with 9 steps
1: benzoyl peroxide
2: HCl / acetonitrile
3: N-iodosuccinimide, 4 Angstroem sieves / CH2Cl2; tetrahydrofuran
4: H2 / Pd-C / ethyl acetate / 2.5 h / 3102.9 Torr / Ambient temperature
5: bovine intestinal alkaline phosphatase
6: benzoyl peroxide / acetonitrile / 2 h / 0 °C
7: N-iodosuccinimide, 4 Angstroem sieves / CH2Cl2; tetrahydrofuran
8: H2 / Pd-C / ethyl acetate / 2.5 h / 3102.9 Torr / Ambient temperature
9: bovine intestinal alkaline phosphatase, or incubation in mouse plasma at 37 deg C
View Scheme
Multi-step reaction with 5 steps
1: benzoyl peroxide
2: HCl / acetonitrile
3: N-iodosuccinimide, 4 Angstroem sieves / CH2Cl2; tetrahydrofuran
4: H2 / Pd-C / ethyl acetate / 2.5 h / 3102.9 Torr / Ambient temperature
5: bovine intestinal alkaline phosphatase
View Scheme
C54H60ClNO18S2

C54H60ClNO18S2

A

C52H59NO17S2

C52H59NO17S2

B

taxol
33069-62-4

taxol

Conditions
ConditionsYield
With ammonia In methanol at 0℃; for 1.5h; Inert atmosphere;A 67%
B 88 mg
13-[(2'R,3'S)-3'-benzoylamino-3'-phenyl-2'-hydroxypropinonyl]-7-trichloroacetylbaccatin III
1033962-72-9

13-[(2'R,3'S)-3'-benzoylamino-3'-phenyl-2'-hydroxypropinonyl]-7-trichloroacetylbaccatin III

taxol
33069-62-4

taxol

Conditions
ConditionsYield
With methanol; ammonium acetate In tetrahydrofuran for 4h;80%
With ammonium acetate In tetrahydrofuran; methanol for 4h;80%
2'-O-benzoyl-3'-N-debenzoyl-paclitaxel
307923-51-9

2'-O-benzoyl-3'-N-debenzoyl-paclitaxel

taxol
33069-62-4

taxol

Conditions
ConditionsYield
With anthranilic acid; triethylamine In tetrahydrofuran; ethyl acetate65%
In dimethyl sulfoxide at 20℃;
C130H180N2O28Si4

C130H180N2O28Si4

taxol
33069-62-4

taxol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 5h;91.8%
C124H168N2O28Si4

C124H168N2O28Si4

taxol
33069-62-4

taxol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 5h;91.5%
C62H73NO16Si
718627-80-6

C62H73NO16Si

taxol
33069-62-4

taxol

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; methanol; water for 0.666667h;82%
succinic acid anhydride
108-30-5

succinic acid anhydride

C52H60N2O16S2

C52H60N2O16S2

A

C56H64N2O19S2

C56H64N2O19S2

B

taxol
33069-62-4

taxol

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;A 29%
B 80 mg
...Expand
2’-TES-7-TROC-taxol
219780-99-1

2’-TES-7-TROC-taxol

taxol
33069-62-4

taxol

Conditions
ConditionsYield
With acetic acid; zinc84%
With acetic acid; zinc at 20℃; for 16h; deacylation;84%
13-(O-2R-hydroxy-3S-amine-phenylpropionyl)-baccatin III
133524-70-6

13-(O-2R-hydroxy-3S-amine-phenylpropionyl)-baccatin III

benzoyl chloride
98-88-4

benzoyl chloride

taxol
33069-62-4

taxol

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; potassium dihydrogenphosphate; sodium chloride In tetrahydrofuran; water at 20℃; for 0.25 - 0.5h;70%
With triethylamine In acetonitrile at 20℃; for 0.5h; Purification / work up;
With triethylamine In acetonitrile at 20℃; for 0.5h;
acetic anhydride
108-24-7

acetic anhydride

10-deacetylpaclitaxel
78432-77-6

10-deacetylpaclitaxel

taxol
33069-62-4

taxol

Conditions
ConditionsYield
Stage #1: 10-deacetylpaclitaxel With Chloroacetamide In tetrahydrofuran at 100℃; for 3h;
Stage #2: acetic anhydride In tetrahydrofuran at 100℃; for 3h;
Stage #3: With methanol; sodium hydrogencarbonate; thiourea at 20℃; for 1h; Product distribution / selectivity;		78.8%
Stage #1: 10-deacetylpaclitaxel With pyridine; Chloroacetamide at 20℃; for 1h;
Stage #2: acetic anhydride With pyridine In tetrahydrofuran at 100℃; for 0.5h;
Stage #3: With methanol; sodium hydrogencarbonate; thiourea at 20℃; for 1h; Product distribution / selectivity;		60%
Stage #1: 10-deacetylpaclitaxel With Chloroacetamide In tetrahydrofuran at 100℃; for 3h;
Stage #2: acetic anhydride In tetrahydrofuran at 100℃; for 3h;
Stage #3: With sodium hydrogencarbonate; thiourea In methanol at 20℃; for 1h; Product distribution / selectivity;
C57H73NO15Si
115437-19-9

C57H73NO15Si

taxol
33069-62-4

taxol

Conditions
ConditionsYield
With hydrogenchloride; ethanol at 0℃; for 30h;89%

Paclitaxel Chemical Properties

Systematic Name: (2alpha,5beta,7beta,10beta,13alpha)-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
Synonyms of Paclitaxel (CAS NO.33069-62-4): 7,11-Methano-5H-cyclodeca[3,4]benz[1,2-b]oxete benzenepropanoic acid deriv ; Taxal ; Taxol A
Molecular Formula: C47H51NO14
Molecular Weight: 853.92
Molecular Structure:
H bond acceptors: 15
H bond donors: 4
Freely Rotating Bonds: 17
Polar Surface Area: 221.29 Å2
Index of Refraction: 1.637
Molar Refractivity: 219.267 cm3
Molar Volume: 610.556 cm3
Surface Tension: 68.487 dyne/cm
Density: 1.399 g/cm3
Flash Point: 532.644 °C
Enthalpy of Vaporization: 145.984 kJ/mol
Boiling Point: 957.115 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25 °C
Melting Point : 213 °C
Appearance: White Powder
Solubility: solubile in methanol: 50 mg/mL, clear, colorless
Stability: Stable. Incompatible with strong oxidizing agents. Combustible. 
Product Categories of Paclitaxel (CAS NO.33069-62-4): Active Pharmaceutical Ingredients; Pharmaceutical material and intermeidates; Antineoplastics;Antineoplastic; APIs; Antitumors for Research and Experimental Use; Biochemistry; Natural Plant Extract; Intermediates & Fine Chemicals; Pharmaceuticals; Natural Anti-cancer Medical Materials and It's Derivatives; Antitumour; Signalling

Paclitaxel Uses

  Paclitaxel (CAS NO.33069-62-4) can be used to treat patients with breast cancer,lung, ovarian,  head and neck cancer, and advanced forms of Kaposi's sarcoma. Besides, it is also can be used for the prevention of restenosis. And Paclitaxel also can be used in the study of structure and function of microtubles into tubulin.

Paclitaxel Production

From 1967 to 1993,  Paclitaxel (CAS NO.33069-62-4) was derived from bark from the Pacific yew, the harvesting of which kills the tree in the process. From the late 1970s, chemists attempted a total synthesis of the molecule, starting from petrochemical-derived starting materials.

Paclitaxel Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 15mg/kg (15mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION		 National Technical Information Service. Vol. PB83-170969,
mouse LD50 intraperitoneal 128mg/kg (128mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER National Technical Information Service. Vol. PB83-170969,
mouse LD50 intravenous 12mg/kg (12mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Pharmaceutical Research. Vol. 4, Pg. 162, 1987.
rat LD50 intraperitoneal 32530ug/kg (32.53mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 National Technical Information Service. Vol. PB83-170969,
rat LDLo intravenous 85mg/kg (85mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE		 Journal of Toxicological Sciences. Vol. 19(Suppl,
women LDLo intravenous 4995mg/kg/3H- (4995mg/kg) CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION

BLOOD: LEUKOPENIA

BLOOD: THROMBOCYTOPENIA		 Lancet. Vol. 343, Pg. 727, 1994.

Paclitaxel Safety Profile

Safety Information about  Paclitaxel (CAS NO.33069-62-4):
Hazard Codes: HarmfulXn
Risk Statements: 37/38-41-42/43-62-68-40-48-20/21/22
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed. 
R37/38: Irritating to respiratory system and skin. 
R40: Limited evidence of a carcinogenic effect.
R41: Risk of serious damage to the eyes. 
R42/43: May cause sensitization by inhalation and skin contact. 
R48: Danger of serious damage to health by prolonged exposure. 
R62: Risk of impaired fertility. 
R68: Possible risk of irreversible effects.
Safety Statements: 22-26-36/37/39-45
S22: Do not breathe dust. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection. 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: 1544
WGK Germany: 3
RTECS: DA8340700
F: 10-21
HazardClass: 6.1(b)
PackingGroup: III

Paclitaxel Specification

  Paclitaxel (CAS NO.33069-62-4), its Synonyms are 7,11-Methano-5H-cyclodeca[3,4]benz[1,2-b]oxete benzenepropanoic acid deriv ; Taxal ; Taxol A  .

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