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
• Article Data: 56

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

Description

Baccatine III is a tetracyclic diterpenoid compound isolated from plant species of the genus Taxus. It is a white to off-white powder and serves as a crucial precursor in the synthesis of the chemotherapeutic drug paclitaxel. Baccatine III possesses significant potential in various applications due to its unique chemical properties and biological activities.

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 
• 67-56-1 methanol 
• 71610-00-9 Cephalomannine 
• 33069-62-4 taxol 
• 32981-86-5 10-deacetylbaccatin III 
• 115437-21-3 7-(triethylsilyl)baccatin III 
• 150541-99-4 7,13-O,O-Bis(triethylsilyl)baccatin III 
• 591-51-5 phenyllithium 
• 187961-12-2 C₂₈H₃₃Cl₃O₁₃ 
• 72-89-9 acetylcoenzyme A 
• 76446-91-8 13-acetyl baccatin III 
• 142203-65-4 13-acetyl-9-dihydrobaccatin III 
• 290815-48-4 7-epi-13-acetylbaccatin III 

Downstream Products

• 76446-91-8 13-acetyl baccatin III 
• 92950-44-2 7,13-diacetyl baccatin III 
• 150930-82-8 C₃₃H₄₀O₁₁S₂ 
• 115437-21-3 7-(triethylsilyl)baccatin III 
• 32981-89-8 13-oxobaccatin III 
• 204579-93-1 C₄₄H₄₈O₁₂ 
• 848250-71-5 C₄₄H₄₆O₁₂ 
• 265659-42-5 7-(1,2-O-isopropylidene-malyl) baccatin III 
• 32981-86-5 10-deacetylbaccatin III 
• 71629-92-0 10-deacetyl-7-epi-baccatin III 
• 31077-81-3 7-epi-baccatine III 
• 155370-94-8 C₄₃H₆₆O₁₀Si₂ 
• 155370-93-7 7,13-Bis(triethylsilyl)baccatin 1-xanthane 

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.

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.

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.

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.