76215-41-3

Basic information

• Product Name: methyl (9xi,11beta,12alpha,13beta,15beta)-3-{[(2E)-3,4-dimethylpent-2-enoyl]oxy}-11,12,15-trihydroxy-2,16-dioxo-13,20-epoxypicras-3-en-21-oate
• CAS NO: 76215-41-3
• Molecular Formula: C₂₈H₃₆O₁₁
• Molecular Weight: 548.5788
• Mol File: 76215-41-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 742.2°C at 760 mmHg
• Flash Point: 243.5°C
• Density: 1.41g/cm³
• Vapor Pressure: 1.99E-25mmHg at 25°C
• Refractive Index: 1.597
• CAS DataBase Reference: methyl (9xi,11beta,12alpha,13beta,15beta)-3-{[(2E)-3,4-dimethylpent-2-enoyl]oxy}-11,12,15-trihydroxy-2,16-dioxo-13,20-epoxypicras-3-en-21-oate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (9xi,11beta,12alpha,13beta,15beta)-3-{[(2E)-3,4-dimethylpent-2-enoyl]oxy}-11,12,15-trihydroxy-2,16-dioxo-13,20-epoxypicras-3-en-21-oate(76215-41-3)
• EPA Substance Registry System: methyl (9xi,11beta,12alpha,13beta,15beta)-3-{[(2E)-3,4-dimethylpent-2-enoyl]oxy}-11,12,15-trihydroxy-2,16-dioxo-13,20-epoxypicras-3-en-21-oate(76215-41-3)

Safety Data

• Hazardous Substances Data: 76215-41-3(Hazardous Substances Data)

Upstream product

• 63306-30-9 bruceoside-A 
• 76215-42-4 15-desenecioyl bruceoside-A 
• 38972-59-7 trans-3,4-dimethyl-2-pentenoic acid 
• 21016-44-4 ethyl (E)-3,4-dimethyl-2-pentenoate 
• 563-80-4 3-methyl-butan-2-one 
• 76215-43-5 (E)-3,4-dimethylpent-4-enoyl chloride 

Downstream Products

• 76215-40-2 3,15-bis(3,4-dimethyl-2-pentenoyl)bruceolide 

Relevant articles and documents

Antitumor Agents. 43. Conversion of Bruceoside-A into Bruceantin

Bruceoside-A (1) has been converted by two methods to bruceantin (5), a potent antileukemic agent.The first method involved the hydrolysis of 1 with potassium hydroxide followed by p-toluenesulfonic acid in methanol to afford 49percent bruceolide (2).Esterification of 2 with 3,4-dimethyl-2-pentenoyl chloride (9) yielded the corresponding 3,15-diester (3) (47percent) and the 3-monoester (4) (31percent).Compound 4 was reconverted to 3 (77percent) by further esterification.Selective hydrolysis of 3 with p-toluenesulfonicacid afforded 5 in 40percent yield.The second method included the hydrolysis of 1 with potassium hydroxide to yield 57percent 15-desenecioyl bruceoside-A (6).Boron trifluoride etherate hydrolysis of the 3,4-dimethyl-2-pentenoyl ester (7), prepared by esterification of 6 with the corresponding acid chloride, gave 5 in 58percent yield.