Paclitaxel

Base Information

• Chemical Name: Paclitaxel
• CAS No.: 33069-62-4
• Deprecated CAS: 157069-30-2,1203669-79-7
• Molecular Formula: C47H51NO14
• Molecular Weight: 853.92
• Hs Code.: 2939.90
• European Community (EC) Number: 608-826-9
• NSC Number: 745099,125973
• UN Number: 2811
• UNII: P88XT4IS4D,3PPC5TL76P
• DSSTox Substance ID: DTXSID9023413
• Nikkaji Number: J17.834I
• Wikipedia: Paclitaxel
• Wikidata: Q423762
• NCI Thesaurus Code: C1411
• RXCUI: 56946
• Pharos Ligand ID: F6F6DK8FGGAH
• Metabolomics Workbench ID: 43441
• ChEMBL ID: CHEMBL428647
• Mol file: 33069-62-4.mol

Synonyms:33069-62-4;P88XT4IS4D;Paclitaxel;Taxol;Taxol A;Yewtaxan;Genaxol;Plaxicel;Abraxane;Ebetaxel;Genetaxyl;Capxol;Paxene;Onxol;Cyclopax;Genexol;Intaxel;Mitotax;Pacliex;TaxAlbin;OncoGel;Paxceed;EmPAC;Onxal;Zisu;Taxus stent;Taxus Liberte;ABI-007;Padexol;nab-paclitaxel;EndoTAG 1;LipoPac;Tocosol Paclitaxel;(-)-Paclitaxel;Nanoxel;Paclitaxol;Sindaxel;NSC-125973;Coroflex Please;Cypher select;Taxus Express;LEP-ETU;Genexol-PM;(NAB)-Paclitaxel;MBT 0206;BMS 181339-01;Cynviloq;Infinnium;HSDB 6839;ABI 007;DHP 107;DHP-107;Abraxane I.V. Suspension;BMS-181339-01;UNII-P88XT4IS4D;DRG-0190;Paclitaxel (Taxol);NK 105;Paclitaxel (taxus canadensis);NSC 125973;QW 8184;EndoTAG-1;CCRIS 8143;Liposome-entrapped paclitaxel easy-to-use;DTXSID9023413;CHEBI:45863;ABI-007 COMPONENT PACLITAXEL;IG 001;NK-105;NSC125973;5beta,20-Epoxy-1,2-alpha,4,7beta,10beta,13alpha-hexahydroxytax-11-en-9-one 4,10-diacetate 2-benzoate 13-ester with (2R,3S)-N-benzoyl-3-phenylisoserine;QW-8184;nabpaclitaxel;CHEMBL428647;DTXCID603413;(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-9-(((2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl)oxy)-12-(benzoyloxy)-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b-diyl diacetate;ORAXOL COMPONENT PACLITAXEL;Paclitaxel [USAN:USP:INN:BAN];Abraxane (albumin-bound suspension);ABRAXANE COMPONENT PACLITAXEL;MBT-0206;ABI 007 COMPONENT PACLITAXEL;(2aR-(2aalpha,4beta,4abeta,6beta,9alpha(alpha R*,betaS*),11alpha,12alpha,12balpha))-beta-(Benzoylamino)-alpha-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;NCGC00164367-01;NAB-PACLITAXEL COMPONENT PACLITAXEL;MFCD00869953;PACLITAXEL (MART.);PACLITAXEL [MART.];PACLITAXEL (USP-RS);PACLITAXEL [USP-RS];(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl benzoate;PACLITAXEL (EP MONOGRAPH);PACLITAXEL (USP IMPURITY);PACLITAXEL [EP MONOGRAPH];PACLITAXEL [USP IMPURITY];PACLITAXEL (USP MONOGRAPH);PACLITAXEL [USP MONOGRAPH];Xorane;7,11-Methano-1H-cyclodeca[3,4]benz[1,2-b]oxete, benzenepropanoic acid deriv.;SMR000857385;SR-01000075350;Paclitaxel [USAN:BAN:INN];paclitaxelum;Anzatax;Nanotaxel;Paclical;Pacligel;Paxoral;Bris Taxol;C47-H51-N-O14;Taxol, Bris;Paclitaxel,(S);Abraxane (TN);(2alpha,5beta,7beta,10beta,13alpha)-4,10-bis(acetyloxy)-1,7-dihydroxy-13-({(2R,3S)-2-hydroxy-3-phenyl-3-[(phenylcarbonyl)amino]propanoyl}oxy)-9-oxo-5,20-epoxytax-11-en-2-yl benzoate;(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-Dodecahydro-4,6,9,11,12,12b-hexahydroxy-4a,8,13,13-tetramethyl-7,11-methano-5H-cyclodeca(3,4)benz(1,2-b)oxet-5-one 6,12b-diacetate, 12-benzoate, 9-ester with (2R,3S)-N-benzoyl-3-phenylisoserine;[diacetoxy-[(2R,3S)-3-benzamido-2-hydroxy-3-phenyl-propanoyl]oxy-dihydroxy-tetramethyl-oxo-[?]yl] benzoate;4alpha,10beta-bis(acetyloxy)-13alpha-((2S,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyloxy)-1,7beta-dihydroxy-9-oxo-5beta,20-epoxytax-11-en-2alpha-yl benzoate;4alpha,10beta-bis(acetyloxy)-13alpha-[(2S,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyloxy]-1,7beta-dihydroxy-9-oxo-5beta,20-epoxytax-11-en-2alpha-yl benzoate;5?,20-Epoxy-1,7?-dihydroxy-9-oxotax-11-ene-2?,4,10?,13?-tetrayl 4,10-diacetate 2-benzoate 13-[(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate];BENZENEPROPANOIC ACID, .BETA.-(BENZOYLAMINO)-.ALPHA.-HYDROXY-, (2AR,4S,4AS,6R,9S,11S,12S,12AR,12BS)-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, (.ALPHA.R,.BETA.S)-;Benzenepropanoic acid, .beta.-(benzoylamino)-.alpha.-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-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, (.alpha.R,.beta.S)-;Taxol (Paclitaxel);CAS-33069-62-4;PACITAXEL;BMS-181339;Paclitaxel-SSMM-VIP;P-SSMM-VIP;PACLITAXEL [MI];PACLITAXEL [INN];PACLITAXEL [JAN];Prestwick3_000155;PACLITAXEL [HSDB];PACLITAXEL [USAN];TAXOL (TN);PACLITAXEL [VANDF];SCHEMBL3976;3PPC5TL76P;Nova-12005;PACLITAXEL [WHO-DD];Paclitaxel, Taxus brevifolia;BIDD:PXR0046;BSPBio_000290;KBioGR_002509;KBioSS_002517;Paclitaxel (JAN/USP/INN);MLS002154218;MLS002695976;OAS-PAC-100;PACLITAXEL [EMA EPAR];BPBio1_000320;GTPL2770;MEGxp0_001940;Taxol (TN) (Bristol Meyers);PACLITAXEL [GREEN BOOK];PACLITAXEL [ORANGE BOOK];ACon1_002231;KBio2_002509;KBio2_005077;KBio2_007645;KBio3_002987;ANX-513;DHP-208;DTS-301;L01CD01;SDP-013;cMAP_000068;HMS2090D07;HMS2095O12;HMS2231A16;HMS3712O12;[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate;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))-;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))-;HY-B0015;MPI-5018;Tax-11-en-9-one, 5beta,20-epoxy-1,2alpha,4,7beta,10beta,13alpha- hexahydroxy-, 4,10-diacetate 2-benzoate, 13-ester with (2R,3S)-N-benzoyl-3-phenylisoserine;Tox21_112107;BDBM50001839;NSC745099;AKOS007930675;AKOS015969673;AKOS025312303;CCG-220155;CS-1145;DB01229;GS-6554;NSC-745099;NCGC00164367-02;NCGC00164367-03;NCGC00164367-04;NCGC00164367-05;NCGC00164367-10;Paclitaxel, From Taxus brevifolia, 95%;NCI60_000601;Paclitaxel, from Taxus yannanensis, powder;PACLITAXEL IMPURITY L [EP IMPURITY];AB00513812;D00491;EN300-117275;M02242;N88686;AB00513812-02;AB00513812-03;Paclitaxel, Antibiotic for Culture Media Use Only;Q423762;7,4]benz[1,2-b]oxete,benzenepropanoic acid deriv.;Q-201533;SR-01000075350-1;SR-01000075350-3;SR-01000075350-6;SR-01000075350-7;SR-01000075350-9;BRD-K62008436-001-03-1;BRD-K62008436-001-05-6;BRD-K62008436-001-22-1;Paclitaxel, from semisynthetic (from Taxus sp.), >=97%;Paclitaxel, European Pharmacopoeia (EP) Reference Standard;Paclitaxel, from Taxus brevifolia, >=95% (HPLC), powder;Paclitaxel, United States Pharmacopeia (USP) Reference Standard;12-benzoate, 9-ester with (2R,3S)-N-benzoyl-3-phenylisoserine;Paclitaxel, Pharmaceutical Secondary Standard;Certified Reference Material;Paclitaxel natural for peak identification, European Pharmacopoeia (EP) Reference Standard;(1S,2S,3R,4S,5R,7S,8S,10R,13S)-4,10-Diacetoxy-2-benzoyloxy-5,20-epoxy-1,7-dihydroxy-9-oxotax-11-en-13-yl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropionate;(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-Dodecahydro 4,6,9,11,12,12b-hexahydroxy-4a,8,13,13-tetramethyl-7,11-methano 5Hcyclodeca(3,4)benz(1,2-b)oxet-5-one 6,12b-diacetate,;(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-4,6,12b-Tris(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl (alphaR,betaS)-beta-(benzoylamino)-alpha-hydroxybenzenepropanoate;(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-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 (aR,bS)-b-(benzoylamino)-a-hydroxybenzenepropanoate;(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-9-(((2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl)oxy)-12-(benzoyloxy)-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)-diyl diacetate;(2aR-(2aalpha,4beta,4abeta,6beta,9alpha(alpha R*,betaS*),11alpha,12alpha,12balpha))-beta-(Benzoylamino)-alpha-hydroxybenzenepropanoic acid 6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12;[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl]benzoate;1203669-79-7;4,7beta,10beta-tris(acetyloxy)-13alpha-[[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy]-1-hydroxy-9-oxo-5beta,20-epoxytax-11-en-2alpha-yl benzoate;5-BETA,20-EPOXY-1,2-ALPHA,4,7-BETA,10-BETA,13-ALPHA-HEXAHYDROXY-TAX-11-EN-9-ONE 4,10-DIACETATE 2-BENZOATE 13-ESTER WITH (2R,3S)-N-BENZOYL-3-PHENYL-ISOSERINE;5beta,20-Epoxy-1,2 alpha, 4,7beta, 10beta, 13alpha-hexahydroxy tax-11-en-9-one 4,10-diacetate 2-benzoate 13-ester with (2R, 3S)-N-benzoyl-3-phenylisoserine;Benzenepropanoic acid, 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.]]-;Benzenepropanoic acid, b-(benzoylamino)-.alpha.-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-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, (aR,bS)-;Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-4,6,12b-tris(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, (alphaR,betaS)-;Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-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;Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-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, (alphaR,betaS)-;Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, 4,6,12b-tris(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-11-hydroxy-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]]-;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;Paclitaxel semi-synthetic for peak identification, European Pharmacopoeia (EP) Reference Standard;Paclitaxel semi-synthetic for system suitability, European Pharmacopoeia (EP) Reference Standard;TAX-11-EN-9-ONE, 5-BETA,20-EPOXY-1,2-ALPHA,4,7-BETA,10-BETA,13-ALPHA-HEXA-HYDROXY-, 4,10-DIACETATE 2-BENZOATE 13-ESTER WITH (2R,3S)-N-BENZOYL-3-PHENYLISOSERINE;TAX-11-EN-9-ONE, 5BETA,20-EPOXY-1,2ALPHA,4,7BETA,10BETA,13ALPHA-HEXAHYDROXY-, 4,10-DIACETATE 2-BENZOATE 13-ESTER WITH (2R,3S)-N-BENZOYL-3-PHENYLISOSERINE;Tax-11-en-9-one, 5beta,20-epoxy-1,2alpha,4,7beta,10beta,13alpha-hexahydroxy-, 4,10-diacetate 2-benzoate 13-ester with (2R,3S)-N-benzoyl-3-phenylisoserine (8CI);Tax-11-en-9-one, 5beta,20-epoxy-1,2alpha,4,7beta,10beta,13alpha-hexahydroxy-, 4,10-diacetate 2-benzoate, 13-ester with (2R,3S)-N-benzoyl-3-phenylisoserine;Tax-11-en-9-one,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

Chemical Property of Paclitaxel

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 213 °C
• Refractive Index: -49 ° (C=1, MeOH)
• Boiling Point: 957.115 °C at 760 mmHg
• PKA: 11.90±0.20(Predicted)
• Flash Point: 532.644 °C
• PSA: 221.29000
• Density: 1.39 g/cm³
• LogP: 4.12660
• Storage Temp.: 2-8°C
• Solubility.: methanol: 50 mg/mL, clear, colorless
• Water Solubility.: 0.3mg/L(37 oC)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 14
• Exact Mass: 853.33095530
• Heavy Atom Count: 62
• Complexity: 1790
• Transport DOT Label: Poison

Purity/Quality:

99%, ^*data from raw suppliers

Paclitaxel ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R40:; R41:
• Hazard Codes: Xn
• Statements: 37/38-41-42/43-62-68-40-48-20/21/22-68/20/21/22
• Safety Statements: 22-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• Drug Classes: Antineoplastic Agents
• Canonical SMILES: CC1=C2C(C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1OC(=O)C(C(C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)O)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)O)C)OC(=O)C
• Isomeric SMILES: CC1=C2[C@H](C(=O)[C@@]3([C@H](C[C@@H]4[C@]([C@H]3[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)O)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)O)C)OC(=O)C
• Recent ClinicalTrials: Paclitaxel and Carboplatin With or Without Bevacizumab in Treating Patients With Stage II, Stage III, or Stage IV Ovarian Epithelial Cancer, Primary Peritoneal Cancer, or Fallopian Tube Cancer
• Recent EU Clinical Trials: A Phase 1/2 Open-Label, Umbrella Platform Design Study of Investigational Agents With Pembrolizumab (MK-3475) in Participants With Advanced Esophageal Cancer Previously Exposed to PD-1/PD-L1 Treatment (KEYMARKER-U06): Substudy 06B.
• Recent NIPH Clinical Trials: Phase 3 study of pembrolizumab vs chemotherapy in dMMR advanced or recurrent endometrial carcinoma
• General Description: Paclitaxel (also known as Taxol) is a potent chemotherapeutic agent widely used in cancer treatment, particularly for breast, ovarian, and lung cancers. It functions by stabilizing microtubules, inhibiting their disassembly, and thereby disrupting cell division. Paclitaxel has inspired the development of numerous analogs and derivatives, such as modified phenylisoserine side chain variants and 7-deoxy-6-hydroxy isomers, which retain comparable antitumor activity while potentially improving stability or solubility. Additionally, novel delivery systems, like NT4 peptide-based conjugates, aim to enhance its targeting and efficacy while reducing side effects. Its complex structure has also driven extensive synthetic research, including ring-closing metathesis for BC ring formation and streamlined A-ring synthesis, contributing to the broader development of taxane-based therapeutics.

Technology Process of Paclitaxel

There total 352 articles about Paclitaxel which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

dmap (1122-58-3) → taxol (33069-62-4)

Guidance literature:

With hydrogenchloride; water; In ethanol; at 0 - 20 ℃; for 2.41667h;

Reference yield: 100.0%

7-O-(triethylsilyl)paclitaxel (148930-55-6) → taxol (33069-62-4)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; Ambient temperature;

DOI:10.1246/cl.1998.3

Reference yield: 99.0%

(2'R,3S)-2'-(2-methoxy-2-propyloxy)-7-triethylsilyl taxol → taxol (33069-62-4)

Guidance literature:

With pyridine; hydrogen fluoride; In water; acetonitrile; at 0 - 25 ℃; for 18h;

upstream raw materials:

acetic anhydride

C₅₀H₅₂Cl₃NO₁₆

7-(triethylsilyl)baccatin III

(4S,5S)-3-benzoyl-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid

Downstream raw materials:

3-Benzoylamino-2-hydroxy-3-phenyl-propionic acid methyl ester

2',7-disuccinyltaxol

2'-succinylpaclitaxel

paclitaxel-2-O-hemiglutarate

Refernces

Design, synthesis, and antitumor activity evaluation of pretubulysin analogs

10.1111/cbdd.13852

The research focuses on the design, synthesis, and antitumor activity evaluation of pretubulysin analogs, which are structurally simpler than the naturally occurring pretubulysin and exhibit potent biological activity against various tumor cell lines. The study aimed to overcome the commercialization challenges posed by the complex structure of pretubulysin by designing and synthesizing a series of 2-(3-(methylamino)propyl)thiazole-4-carboxamides. The antitumor activities of these compounds were screened using MCF-7 (breast cancer) and NCI-H157 (lung cancer) cell lines, with Taxol and pretubulysin serving as controls. The synthesis involved a three-step process, including cyclization, bromination, and a Witting reaction, followed by reduction and hydrolysis to yield the desired compounds. The synthesized compounds were characterized using NMR spectroscopy and high-resolution mass spectrometry (HRMS), and their cytotoxicity was assessed through a mitochondrial-dependent reduction of MTT to formazan, measured spectrophotometrically. Additionally, molecular docking studies were conducted to understand the compounds' interaction with tubulin, using the co-crystal structure of microtubules and tubulysin M. The experiments revealed that certain analogs, such as compounds 8c and 8h, exhibited antitumor activities comparable to those of Taxol, suggesting their potential as novel antitumor drugs.

Synthesis of BC ring-systems of taxol by ring-closing metathesis

10.1055/s-2000-6263

The research focuses on the synthesis of the BC ring-systems of the antitumor agent Taxol (also known as paclitaxel), which is a significant challenge in organic chemistry. The study aims to develop a convergent approach to Taxol's total synthesis, with a key step involving a ring-closing metathesis (RCM) reaction to form the BC ring-system by creating the C9-C10 bond. The researchers utilized various catalysts, including Grubbs' ruthenium complex, Schrock’s molybdenum compound, and Nolan’s catalyst, to facilitate the RCM reactions. They experimented with different substrates, such as silylene 26, acetonide 27, and carbonate 23, to optimize the synthesis process. The study concluded that the RCM reaction could successfully form the eight-membered BC ring-system of Taxol, and that catalyst [RuIm] was the most active among the tested catalysts. Interestingly, the research also revealed an instance where a trans cyclooctene was formed, indicating that RCM does not always proceed to thermodynamic equilibrium with catalysts [Ru] and [Mo], unlike with [RuIm] which yielded the expected cis product. The chemicals used in this process included a range of olefins, alcohols, and protected derivatives, as well as metathesis precursors synthesized through various organic reactions such as Shapiro coupling and cyanohydrin homologation. The study provides valuable insights into the synthesis of complex molecular structures like Taxol and contributes to the field of organic chemistry and drug development.

Stereospecific synthesis of 7-deoxy-6-hydroxy paclitaxel

10.1016/S0040-4039(99)00864-3

The research describes a stereospecific synthesis of 7-deoxy-6-hydroxy paclitaxel, aiming to improve the chemical and metabolic stability of paclitaxel by transposing the 7-hydroxyl group to the 6-position. Key chemicals involved include tributylgermanium hydride, which was crucial for the stereoselective reduction of the 6,7-α-thiocarbonate, and 1,1-thiocarbonyl diimidazole used in the preparation of the cyclic thiocarbonate. Other reagents such as DMAP, TPAP, and NaBH? were also utilized in various steps of the synthesis. The study successfully synthesized both the 6-α- and 6-β-isomers of 7-deoxy-6-hydroxy paclitaxel, demonstrating their equipotency to paclitaxel in a tubulin polymerization assay, while noting differences in cytotoxicity.

A short synthesis of the A-ring of taxol

10.1016/0040-4020(95)00378-L

This research aims to develop a concise and efficient synthetic route for the A-ring building block of Taxol, a diterpene with significant antitumor activity but limited natural availability. The study presents a seven-step synthesis starting from an inexpensive mixture of E- and Z-citrals, which are converted to safranal through a series of reactions including cyclization, bromination, and dehydrobromination. Safranal is described as a key intermediate in the synthesis of the A-ring building block for Taxol. It is the major constituent of saffron oil and can be prepared from the inexpensive citral in a few steps. Safranal is used as a starting material to introduce the necessary functional groups and stereochemistry required for the A-ring of Taxol. The researchers reasoned that reduction of the aldehyde function of safranal to an allylic alcohol, followed by protection as the pivalate, would lead to the conjugated allylic pivalate, which could then be further transformed into the desired ketone through allylic oxidation and 1,4-reduction. The authors conclude that their method is advantageous due to its brevity and simplicity, making it a viable alternative for synthesizing the A-ring building block, especially for the development of simpler Taxol analogs with potentially better solubility and therapeutic properties.

A new NT4 peptide-based drug delivery system for cancer treatment

10.3390/molecules25051088

The research presents the development of a novel drug delivery system leveraging a tetrabranched peptide, NT4, for cancer treatment. The system is designed to selectively target cancer cells, enhancing the efficacy of chemotherapy drugs like paclitaxel while minimizing side effects. The study involved synthesizing NT4 conjugated with varying numbers of paclitaxel units and creating an NT4-based nanosystem integrated with near-infrared (NIR) emitting quantum dots (QDs) for simultaneous tumor detection and destruction. Experiments conducted include in vitro cytotoxicity assays on human colon adenocarcinoma cell lines (HT-29) to evaluate the binding and cytotoxic effects of NT4-QD-PTX conjugates compared to unlabeled QD-PTX. The research utilized techniques such as solid-phase peptide synthesis, Michael reactions for conjugation, and HPLC purification. The analyses included NMR spectroscopy, mass spectrometry, and flow cytometry to confirm the structure, purity, and biological activity of the synthesized compounds and nanodevices.

Synthesis of biologically active taxol analogues with modified phenylisoserine side chains

10.1021/jm00100a031

The study reports on the synthesis and biological evaluation of taxol derivatives with substituted phenyl rings at the C-13 N-benzoyl-(2'R,3'S)-3'-phenylisoserine side chain of taxol. The researchers synthesized two taxol analogues: one with a N-@-chlorobenzoyl)-(2'R,3'S)-3'-phenylisoserine side chain (2) and another with a N-benzoyl-(2'R,3'S)-3'-(p-chlorophenyl)isoserine side chain (3). The synthesis involved the asymmetric synthesis of 3-hydroxy-4-aryl-2-azetidinone derivatives via the ester enolate-imine cyclocondensation reaction, followed by acylation and coupling reactions. The newly synthesized derivatives 2 and 3 were tested for their ability to promote tubulin assembly and their cytotoxicity against B16 melanoma cells. The results showed that both analogues had activity comparable to taxol, indicating that the introduction of p-chloro substituents at the phenyl groups did not significantly alter the biological activity of taxol.