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33069-62-4

Basic Information
CAS No.: 33069-62-4
Name: Paclitaxel
Article Data: 81
Cas Database
Molecular Structure:
Molecular Structure of 33069-62-4 (Paclitaxel)
Formula: C47H51NO14
Molecular Weight: 853.92
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;
EINECS: 205-285-7
Density: 1.39 g/cm3
Melting Point: 213 °C
Boiling Point: 957.115 °C at 760 mmHg
Flash Point: 532.644 °C
Solubility: solubile in methanol: 50 mg/mL, clear, colorless
Appearance: white powder
Hazard Symbols: R40:; R41:;
Risk Codes: 37/38-41-42/43-62-68-40-48-20/21/22
Safety: 22-26-36/37/39-45
Transport Information: N/A
PSA: 221.29000
LogP: 4.12660
Synthetic route
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]

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

98-88-4

benzoyl chloride

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

98-88-4

benzoyl chloride

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

98-88-4

benzoyl chloride

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%
439813-57-7

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

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

98-88-4

benzoyl chloride

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;
158722-23-7

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

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

C50H59NO14Si

Conditions
ConditionsYield
With hydrogenchloride In water at 20℃;93.3%
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    Product Name: Paclitaxel Synonyms: Paclitaxel HCL;Paclitaxel(natural crude);αR-hydroxy-βS-(benzoylamino)-benzenepropanoic acid, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,

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Chemistry

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

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.

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.

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.

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

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  .