Baccatin III

Base Information

• Chemical Name: Baccatin III
• CAS No.: 27548-93-2
• Molecular Formula: C31H38O11
• Molecular Weight: 586.636
• Hs Code.: 29329990
• European Community (EC) Number: 636-675-9
• UNII: 40K5PZ0K67
• DSSTox Substance ID: DTXSID301029474
• Nikkaji Number: J82.234E
• Wikipedia: Baccatin_III
• Wikidata: Q15410249
• NCI Thesaurus Code: C1436
• Metabolomics Workbench ID: 52081
• ChEMBL ID: CHEMBL288043
• Mol file: 27548-93-2.mol

Synonyms:baccatin III

Chemical Property of Baccatin III

Chemical Property:

• Appearance/Colour: White to off-white powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 229-234 °C
• Refractive Index: 1.5455-1.5475
• Boiling Point: 713.6 °C at 760 mmHg
• PKA: 12.76±0.70(Predicted)
• Flash Point: 226.9 °C
• PSA: 165.89000
• Density: 1.38 g/cm³
• LogP: 1.65260
• Storage Temp.: 2-8°C
• Water Solubility.: insoluble
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 7
• Exact Mass: 586.24141202
• Heavy Atom Count: 42
• Complexity: 1200

Purity/Quality:

99% ^*data from raw suppliers

Baccatin III ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 45-46-22-36/37/38-48/20/22
• Safety Statements: 53-22-26-36/37/39-45-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C(C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1O)O)OC(=O)C5=CC=CC=C5)(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]1O)O)OC(=O)C5=CC=CC=C5)(CO4)OC(=O)C)O)C)OC(=O)C
• Uses: A precursor to Paclitaxel, a neoplasm inhibitor to ovarian and breast cancers found in Taxus species immunomodulator, induces apoptosis Precursor to paclitaxel

Technology Process of Baccatin III

There total 118 articles about Baccatin III 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: 99.0%

C31H38O11*C3H4N2 → baccatin III (27548-93-2)

Guidance literature:

With water-d2; In dichloromethane-d2; at 20 ℃; for 0.5h;

DOI:10.1021/ol006332q

Reference yield: 97.0%

10-deacetylbaccatin III (32981-86-5,172018-16-5) + acetic anhydride (108-24-7) → baccatin III (27548-93-2)

Guidance literature:

lanthanum(lll) triflate; In tetrahydrofuran; for 2h;

DOI:10.1016/S0040-4039(98)01253-2

Reference yield: 97.0%

taxol (33069-62-4) → baccatin III (27548-93-2)

Guidance literature:

With tetrabutylammonium borohydride; In dichloromethane; for 1h;

DOI:10.1021/jo00366a043

upstream raw materials:

10-desacetylbaccatin III

acetic anhydride

methanol

Cephalomannine

Downstream raw materials:

7-(2,2,2-trichloroethyloxycarbonyl)baccatin III

7-(triethylsilyl)baccatin III

10-deacetylbaccatin III

10-desacetoxybaccatin

Refernces

• 1、 You, Lin-Feng,Huang, Jia-Jun,Lin, Shu-Ling,Wei, Tao,Zheng, Qian-Wang,Jiang, Bing-Hua,Lin, Jun-Fang,Guo, Li-Qiong. "In vitro enzymatic synthesis of baccatin III with novel and cheap acetyl donors by the recombinant taxoid 10β-O-acetyl transferase". . p. 239 - 245. Retrieved 2019.
• 2、 Chida, Noritaka,Fukaya, Keisuke,Iiyama, Shota,Mochizuki, Shota,Noguchi, Takashi,Oishi, Takeshi,Saio, Ryosuke,Sato, Takaaki,Watanabe, Ami,Yamaguchi, Yu,Yamamoto, Hiroaki. "Total Synthesis of Paclitaxel". supporting information. . Retrieved 2021/12/27.
• 3、 -. "Fluorinated taxane compound, preparation method therefor and application of fluorinated taxane compound". Paragraph 0048; 0085; 0093-0095. . Retrieved 2019/08/30.