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| CAS No.: | 33069-62-4 |
|---|---|
| Name: | Paclitaxel |
| Molecular Structure: | |
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| 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 |
| PSA: | 221.29000 |
| LogP: | 4.12660 |
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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]
- 33069-62-4
taxol
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| 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
- 33069-62-4
taxol
| Conditions | Yield |
|---|---|
| With hydrogenchloride In ethanol; water at 0℃; for 30h; | 90% |
| With hydrogenchloride In ethanol at 0℃; for 72h; | 80% |
- 33069-62-4
taxol
| Conditions | Yield |
|---|---|
| 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 |
| Conditions | Yield |
|---|---|
| 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
- 33069-62-4
taxol
| Conditions | Yield |
|---|---|
| With hydrogenchloride In methanol at 60 - 80℃; for 3.5h; | 80% |
| With hydrogenchloride In methanol | 76% |
| With hydrogenchloride at 95℃; for 2h; | 75% |
| With hydrogenchloride In methanol at 60℃; for 3h; Hydrolysis; |
- 1122-58-3
dmap
- 33069-62-4
taxol
| Conditions | Yield |
|---|---|
| With hydrogenchloride; water In ethanol at 0 - 20℃; for 2.41667h; | 100% |
- 33069-62-4
taxol
| Conditions | Yield |
|---|---|
| With hydrogenchloride In water at 20℃; | 93.3% |
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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: 
Xn
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 .