6alpha-Hydroxypaclitaxel

Base Information

• Chemical Name: 6alpha-Hydroxypaclitaxel
• CAS No.: 153212-75-0
• Deprecated CAS: 153720-55-9,172228-55-6
• Molecular Formula: C₄₇H₅₁NO₁₅
• Molecular Weight: 869.92
• Hs Code.: 29329990
• European Community (EC) Number: 687-556-3
• UNII: P97L07N47V
• Nikkaji Number: J569.536H
• Wikidata: Q27132865
• Metabolomics Workbench ID: 63010
• ChEMBL ID: CHEMBL3911312
• Mol file: 153212-75-0.mol

Synonyms:6-hydroxy-taxol;6-hydroxypaclitaxel;6-hydroxytaxol;6alpha-hydroxypaclitaxel;6alpha-hydroxytaxol

Chemical Property of 6alpha-Hydroxypaclitaxel

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 177-180 °C
• Refractive Index: 1.646
• Boiling Point: 979.829 °C at 760 mmHg
• PKA: 11.90±0.20(Predicted)
• Flash Point: 546.381 °C
• PSA: 241.52000
• Density: 1.43 g/cm³
• LogP: 3.09740
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 14
• Exact Mass: 869.32586992
• Heavy Atom Count: 63
• Complexity: 1830

Purity/Quality:

98%Min ^*data from raw suppliers

6a-Hydroxy Paclitaxel ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C(C(=O)C3(C(C(C(C2(C)C)(CC1OC(=O)C(C(C4=CC=CC=C4)NC(=O)C5=CC=CC=C5)O)O)OC(=O)C6=CC=CC=C6)C7(COC7C(C3O)O)OC(=O)C)C)OC(=O)C
• Isomeric SMILES: CC1=C2[C@H](C(=O)[C@]3([C@H]([C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](C4=CC=CC=C4)NC(=O)C5=CC=CC=C5)O)O)OC(=O)C6=CC=CC=C6)[C@@]7(CO[C@@H]7[C@H]([C@@H]3O)O)OC(=O)C)C)OC(=O)C
• Uses: The major human metabolite of Paclitaxel The major human metabolite of Paclitaxel.

Technology Process of 6alpha-Hydroxypaclitaxel

There total 14 articles about 6alpha-Hydroxypaclitaxel 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: 85.0%

2'-O-triethylsilylpaclitaxel-6-α-nitrate (212953-29-2) → [3H]-6alpha-Hydroxypaclitaxel (153212-75-0,172228-55-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1016/S0040-4039(00)00707-3

Reference yield: 71.0%

Δ6,7-paclitaxel (158830-49-0) → 6-α-hydroxy-7-α-paclitaxel (153212-75-0,172228-55-6)

Guidance literature:

With osmium(VIII) oxide; N-methyl-2-indolinone; at 25 ℃; for 9h;

DOI:10.1016/0040-4039(95)00431-B

Reference yield: 71.0%

C53H65NO15Si → [3H]-6alpha-Hydroxypaclitaxel (153212-75-0,172228-55-6)

Guidance literature:

With pyridine; hydrogen fluoride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(98)00970-8

upstream raw materials:

Δ^6,7-paclitaxel

6-α-hydroxy-2'-O-triethylsilyl-7-α-paclitaxel

2'-O-triethylsilylpaclitaxel-6-α-nitrate

taxol

Refernces

• 1、 Tsukada, Chiharu,Saito, Takahiro,Maekawa, Masamitsu,Mano, Nariyasu,Oda, Akifumi,Hirasawa, Noriyasu,Hiratsuka, Masahiro. "Functional characterization of 12 allelic variants of CYP2C8 by assessment of paclitaxel 6α-hydroxylation and amodiaquine N-deethylation". . p. 366 - 373. Retrieved 2015.
• 2、 Jiang, Hualin,Zhong, Fangfang,Sun, Lu,Feng, Weiyue,Huang, Zhong-Xian,Tan, Xiangshi. "Structural and functional insights into polymorphic enzymes of cytochrome P450 2C8". . p. 1195 - 1204. Retrieved 2011.
• 3、 Yang, Xin,Johnson, Nathaniel,Di, Li. "Evaluation of Cytochrome P450 Selectivity for Hydralazine as an Aldehyde Oxidase Inhibitor for Reaction Phenotyping". . p. 1627 - 1630. Retrieved 2019/01/16.
• 4、 Albertolle, Matthew E.,Kim, Donghak,Nagy, Leslie D.,Yun, Chul-Ho,Pozzi, Ambra,Savas, üzen,Johnson, Eric F.,Guengerich, F. Peter. "Heme-thiolate sulfenylation of human cytochrome P450 4A11 functions as a redox switch for catalytic inhibition". . p. 11230 - 11242. Retrieved 2017/08/08.