41451-75-6

Basic information

• Product Name: Bruceantin
• Synonyms: Bruceantin;2H-3,11c-(Epoxymethano)phenanthro[10,1-bc]pyran, picras-3-en-21-oic acid deriv.;NCI 165563;NSC 165563;Yadanziyou Oleum Bruceae
• CAS NO: 41451-75-6
• Molecular Formula: C₂₈H₃₆O₁₁
• Molecular Weight: 548.581
• Mol File: 41451-75-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 225-226℃
• Boiling Point: 540.78°C (rough estimate)
• Flash Point: 239.4°C
• Appearance: /
• Density: 1.2262 (rough estimate)
• Vapor Pressure: 1.14E-24mmHg at 25°C
• Refractive Index: 1.5970 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 8.81±0.70(Predicted)
• CAS DataBase Reference: Bruceantin(CAS DataBase Reference)
• NIST Chemistry Reference: Bruceantin(41451-75-6)
• EPA Substance Registry System: Bruceantin(41451-75-6)

Safety Data

• Hazardous Substances Data: 41451-75-6(Hazardous Substances Data)

Usage

Description

Bruceantin is a naturally occurring quassinoid compound found in the plant Brucea antidysenterica. It possesses potent bioactive properties and has been extensively studied for its potential therapeutic applications in various medical fields. Bruceantin exhibits a unique mechanism of action, making it a promising candidate for the development of novel pharmaceuticals.

Uses

Used in Anticancer Applications:
Bruceantin is used as an anticancer agent for its ability to induce apoptosis in human promyelocytic leukemia cells. It targets and disrupts essential cellular processes, leading to the programmed cell death of cancerous cells. This property makes it a valuable tool in the fight against various types of cancer.
Used in Antiamoebic Applications:
Bruceantin is also used as an antiamoebic agent, effectively combating infections caused by the protozoan parasite Entamoeba histolytica. This parasite is responsible for amoebiasis, a disease that can lead to severe gastrointestinal complications if left untreated. Bruceantin's antiamoebic properties make it a potential therapeutic option for treating amoebiasis and reducing the associated health risks.

InChI:InChI=1/C28H36O11/c1-11(2)12(3)7-17(30)39-20-22-27-10-37-28(22,25(35)36-6)23(33)19(32)21(27)26(5)9-15(29)18(31)13(4)14(26)8-16(27)38-24(20)34/h7,11,14,16,19-23,31-33H,8-10H2,1-6H3/b12-7+/t14-,16+,19+,20+,21+,22+,23-,26-,27+,28+/m0/s1

Synthetic route

bruceoside A (63306-30-9, 84607-61-4) → Bruceantin (41451-75-6)

Bruceantin (41451-75-6) + acetic anhydride (108-24-7) → bruceantin monoacetate (71887-23-5)

Conditions	Yield
In pyridine 1.) 0 grad C, 3.5 h, 2.) -20 grad C, overnight.;	97%

Bruceantin (41451-75-6) + acetic anhydride (108-24-7) → 3,11,12-Tri-O-acetylbruceantin (55812-88-9)

Conditions	Yield
With dmap In dichloromethane for 12h; Ambient temperature;	87%

Bruceantin (41451-75-6) + succinoyl dichloride (543-20-4) → bis(brucentinyl)succinate

Conditions	Yield
With pyridine

Bruceantin (41451-75-6) + malonoyl dichloride (1663-67-8) → bis(brucentinyl)malonate

Conditions	Yield
With pyridine

Upstream product

• 63306-30-9 bruceoside A 
• 55812-88-9 3,11,12-Tri-O-acetylbruceantin 
• 123427-42-9 C₃₈H₅₄O₁₃Si 
• 123376-94-3 C₃₁H₄₆O₁₂Si 
• 123376-96-5 C₃₁H₄₄O₁₂Si 
• 123376-92-1 C₃₁H₄₆O₁₁Si 
• 123376-93-2 C₃₁H₄₄O₁₀Si 
• 122554-54-5 11β,12α-Diacetoxy-3-(tert-butyldimethylsiloxy)-13,20-epoxy-2,16-dioxopicras-3-en-21-oic Acid Methyl Ester 
• 38972-59-7 trans-3,4-dimethyl-2-pentenoic acid 

Downstream Products

• 80096-79-3 bis(brucentinyl)malonate 
• 25514-30-1 bruceine C 
• 78338-24-6 bruceantin-5'-ol 
• 78338-23-5 bruceantin 4',5'-epoxide 

Relevant articles and documents

Total synthesis of (±)-bniceantin

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A formal synthesis of bruceantin

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