27548-93-2

Basic information

• Product Name: Baccatine III
• Synonyms: BACCATINE III;BACCATIN III;baccatin Ⅲ;BACCATIN III 98%;(1S)-4α,10β-Bis(acetoxy)-2α-(benzoyloxy)-5β,20-epoxy-1,7β,13α-trihydroxytaxa-11-ene-9-one;(2aR)-6α,12bβ-Bisacetoxy-12β-(benzoyloxy)-1,2aβ,3,4,4a,6,9,10,11,12,12aβ,12b-dodecahydro-4α,9β,11β-trihydroxy-4aα,8,13,13-tetramethyl-7,11-methano-5H-cyclodeca[3,4]benzo[1,2-b]oxete-5-one;(2aR)-6α,12bβ-Diacetoxy-12β-benzoyloxy-1,2aβ,3,4,4a,6,9,10,11,12,12aβ,12b-dodecahydro-4α,9β,11β-trihydroxy-4aα,8,13,13-tetramethyl-7,11α-methano-5H-cyclodeca[3,4]benzo[1,2-b]oxete-5-one;6α,12bβ-Diacetoxy-12β-benzoyloxy-1,2aβ,3,4,4a,6,9,10,11,12,12aβ,12b-dodecahydro-4α,9β,11β-trihydroxy-4aα,8,13,13-tetramethyl-7,11α-methano-5H-cyclodeca[3,4]benzo[1,2-b]oxete-5-one
• CAS NO: 27548-93-2
• Molecular Formula: C₃₁H₃₈O₁₁
• Molecular Weight: 586.63
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics;Chiral Reagents;Heterocycles;Inhibitors
• Mol File: 27548-93-2.mol

Chemical Properties

• Melting Point: 229-234 °C
• Boiling Point: 562.81°C (rough estimate)
• Flash Point: 226.9 °C
• Appearance: White to off-white/Solid
• Density: 1.2062 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5455-1.5475
• Storage Temp.: 2-8°C
• PKA: 12.76±0.70(Predicted)
• Water Solubility: insoluble
• Stability: 4 Year Shelf Life
• CAS DataBase Reference: Baccatine III(CAS DataBase Reference)
• NIST Chemistry Reference: Baccatine III(27548-93-2)
• EPA Substance Registry System: Baccatine III(27548-93-2)

Safety Data

• Hazard Codes: T
• Statements: 45-46-22-36/37/38-48/20/22
• Safety Statements: 53-22-26-36/37/39-45-24/25
• RIDADR: 1544
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 27548-93-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Baccatine III is used as a precursor for the production of paclitaxel, a neoplasm inhibitor effective against ovarian and breast cancers. Its role in the synthesis of paclitaxel is vital, as it contributes to the development of life-saving cancer treatments.
Used in Cancer Treatment:
Baccatine III is used as an immunomodulator and apoptosis inducer in cancer treatment. Its ability to modulate the immune system and induce programmed cell death in cancer cells makes it a valuable compound in the fight against various types of cancer.
Used in Drug Synthesis:
As a precursor to paclitaxel, Baccatine III plays a crucial role in the development of new and innovative drug synthesis methods. Its use in the pharmaceutical industry is essential for the production of effective cancer treatments, ultimately contributing to improved patient outcomes and survival rates.

InChI:InChI=1/C31H38O11/c1-15-19(34)13-31(38)26(41-27(37)18-10-8-7-9-11-18)24-29(6,20(35)12-21-30(24,14-39-21)42-17(3)33)25(36)23(40-16(2)32)22(15)28(31,4)5/h7-11,19-21,23-24,26,34-35,38H,12-14H2,1-6H3/t19-,20-,21+,23+,24+,26-,29+,30-,31+/m0/s1

Upstream product

• 32981-86-5 10-desacetylbaccatin III 
• 108-24-7 acetic anhydride 
• 71610-00-9 Cephalomannine 
• 33069-62-4 taxol 
• 32981-86-5 10-deacetylbaccatin III 
• 591-51-5 phenyllithium 
• 187961-12-2 C₂₈H₃₃Cl₃O₁₃ 
• 72-89-9 acetylcoenzyme A 
• 76446-91-8 13-acetyl baccatin III 
• 64180-78-5 4-bromopent-4-en-1-ol 
• 35804-44-5 ethyl 4-bromo-4-pentenoate 
• 202341-11-5 (1S,2S,3R,4R,6S,7S,8R,12S)-3,7-Dibenzyloxy-6-(3-butenyl)-6-(tert-butyldimethylsiloxy)-2,12-(isopropylidenedioxy)-1,5,5-trimethyl-9-methylenebicyclo[6.4.0]dodecan-4-ol 
• 202341-06-8 (1S,2S,3S,4R,6S,7S,8R,12S)-3,7-Dibenzyloxy-6-(3-butenyl)-4,6-(tert-butylmethylsilylenedioxy)-2,12-(isopropylidenedioxy)-1,5,5-trimethyl-9-methylenebicyclo[6.4.0]dodecane 
• 202341-17-1 (4S,4aS,5S,6S,7R,8R,11S,12S,12aR)-6,12-Dibenzyloxy-11-(tert-butyldimethylsiloxy)-4,5-(isopropylidenedioxy)-4a,8,13,13-tetramethyl-1-methylenetetradecahydro-7,11-methanobenzocyclodecene-7,8-diol 

Downstream Products

• 76497-09-1 C₃₁H₃₆O₁₁ 
• 32981-89-8 13-oxobaccatin III 
• 31077-81-3 7-epi-baccatin III 

Relevant articles and documents

Synthesis, utility, and x-ray crystal structure of novel complexes of baccatin III with imidazole and 2-propanol

(matrix presented) Baccatin III forms crystalline complexes 4 and 5 with imidazole and 2-propanol, respectively. These compounds are useful in the purification of baccatin III from mixtures of taxanes derived from plant-cell fermentation.

In vitro enzymatic synthesis of baccatin III with novel and cheap acetyl donors by the recombinant taxoid 10β-O-acetyl transferase

Despite the importance of baccatin III as a precursor to paclitaxel, a widely used chemotherapeutic agent, efficient enzymatic synthesis methods are lacking. Therefore, in this study, the recombinant taxoid 10β-O-acetyl transferase was prepared to produce baccatin III in vitro. The recombinant enzyme could use vinyl acetate, butyl acetate, sec-butyl acetate, isobutyl acetate, amyl acetate, and isoamyl acetate as novel and cheap alternative acetyl group donors to replace the expensive acetyl CoA for the enzymatic synthesis of baccatin III. A molecular docking study further confirmed that these acetyl donors could reasonably bind to the enzyme molecule. Using the aqueous two-phase bio-catalytic reaction system, hexane and ethyl acetate could increase the yield of product baccatin III by 2.8% and 1.1% respectively. This approach using novel and cheap acetyl donors is promising for the enzymatic synthesis of baccatin III for the future industrial production of paclitaxel.

Selective protection of the C(7) and C(10) hydroxyl groups in 10- deacetyl baccatin III

New protocols for the selective protection of the C(7) and C(10) hydroxyl groups of 10-deacetyl baccatin III are described, leading to more efficient semisyntheses of taxol and taxol analogs. The C(10) hydroxyl group of 10-DAB can be highly selectively acylated or silylated, and subsequent selective protection of the C(7) hydroxyl group then becomes straightforward.

Total Synthesis of Paclitaxel

The total synthesis of paclitaxel (Taxol) is described. Double Rubottom oxidation of the bis(silyl enol ether) derived from a tricarbocyclic diketone effectively installed a bridgehead olefin and C-5/C-13 hydroxy groups in a one-step operation. The novel Ag-promoted oxetane formation smoothly constructed the tetracyclic framework of paclitaxel.

Fluorinated taxane compound, preparation method therefor and application of fluorinated taxane compound

The invention discloses a fluorinated taxane compound, a preparation method therefor and an application of the fluorinated taxane compound. The compound has a structural general formula represented bya formula I. Proven by pharmacological experiments, compared with paclitaxel, a series of fluorinated taxane derivatives synthesized by the method have cytotoxicity superior to that of the paclitaxelto a multidrug-resistant human mammary cancer cell line MCF-7/Adr and an ovarian cancer cell line NCI/Adr and represent cytotoxicity superior to that of the paclitaxel to a colon cancer cell line HCT-116 with overexpressed neoplasm stem cells.

A semi-synthetic taxane derivative and its preparation method and application

The invention discloses a semi-synthetic taxane derivative. An anti-tumor effect test shows that the semi-synthetic taxane derivative has relatively good anti-tumor activity on a human lung adenocarcinoma cell line A549, a human breast cancer cell line MCF-7, a human glioblastoma cell line U251, a human pancreatic cancer cell line PANC-1, a human colon cancer cell line HCT116 and a human non-small lung cancer cell line H460. The semi-synthetic taxane derivative can be used for preparing anti-tumor drugs.

Antagonizing NOD2 Signaling with Conjugates of Paclitaxel and Muramyl Dipeptide Derivatives Sensitizes Paclitaxel Therapy and Significantly Prevents Tumor Metastasis

A noncleavable paclitaxel (PTX) and N-acetylmuramyl-l-alanyl-d-isoglutamine (MDP) derivative conjugate, 22 (DY-16-43), and its analogues were prepared and characterized as antagonists of NOD2 signaling. This conjugate enhanced the antitumor and antimetastatic efficacy of PTX in Lewis lung carcinoma (LLC) tumor-bearing mice. This work first describes a molecular strategy that enables the sensitization of a chemotherapeutic response via antagonizing NOD2 inflammatory signaling and suggests NOD2 antagonist as potential adjunct in treating non-small-cell lung cancer (NSCLC).

Docetaxel side chain 2'-derived novel taxanes antitumor compound as well as synthesis method and application thereof

The invention discloses a docetaxel side chain 2'-derived novel taxanes antitumor compound shown as the general structure formula (I) as well as a synthesis method and application thereof. In the formula, X is N or O, R is H or acetyl, and R' is H, nitryl, cyano, methoxyl or a halogen group. The synthesis method takes 10-deacetylbaccatin is used as a raw material; after 7-OH and 10-OH are protected, condensation with phenylisoserine (side chain) protecting 3'-NHBoc and 2'-OH in the presence of condensation agents DCC (Dicyclohexylcarbodiimide) and DMAP (Dimethylaminopyridine) is performed; esterification with substituted phenyl isoxazole carboxylic acid or substituted phenyl oxadiazole methyl carboxylic acid in the presence of the DCC and the DMAP is performed; finally, a protecting group is removed to obtain the compound. The compound disclosed by the invention has relatively high activity on tumor cells.

Novel taxane anti-tumor compound as well as synthesis method and application thereof

The invention discloses a novel taxane anti-tumor compound shown in a structural formula (I). 10-DAB (10-deacetylbaccatin) is adopted as a raw material, and is condensed with phenylisoserine (side chain) with protected 3'-NH2 and 2'-OH in the presence of condensing agents DCC and DMAP after 7-OH and 10-OH are protected, the side chain and a protecting group on a baccatin ring are simultaneously removed in the presence of zinc powder, and coupling is performed with substituted phenylisoxazole in an alkaline medium to obtain a target product. The compound has relatively high anti-tumor activity. (The structural formula (I) is shown in the description.).

Organocatalytic site-selective acylation of 10-deacetylbaccatin III

Organocatalytic site-selective diversification of 10-deacetylbaccatin III, a key natural product for the semisynthesis of taxol, has been achieved. Various acyl groups were selectively introduced into the C(10)-OH of 10-deacetylbaccatin III. The C(10)-OH selective acylation was also applied to acylative site-selective dimerization of 10-deacetylbaccatin III to provide the structurally defined dimer.