679435-96-2

Basic information

• Product Name: Butanedioic acid, (4-methyl-4-pentenyl)-, dimethyl ester
• CAS NO: 679435-96-2
• Molecular Formula: C12H20O4
• Molecular Weight: 228.288
• Mol File: 679435-96-2.mol

Chemical Properties

• CAS DataBase Reference: Butanedioic acid, (4-methyl-4-pentenyl)-, dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Butanedioic acid, (4-methyl-4-pentenyl)-, dimethyl ester(679435-96-2)
• EPA Substance Registry System: Butanedioic acid, (4-methyl-4-pentenyl)-, dimethyl ester(679435-96-2)

Safety Data

• Hazardous Substances Data: 679435-96-2(Hazardous Substances Data)

Upstream product

• 25163-50-2 4-methyl-4-pentenyl-1-tosylate 
• 41182-50-7 5-bromo-2-methyl-1-pentene 
• 4911-54-0 ethyl 4-methyl-4-pentenoate 
• 22508-64-1 4-methyl-4-penten-1-ol 
• 679435-44-0 dimethyl (Z)-2-(2-methyl)pentenylbutenedioate 

Relevant articles and documents

Synthesis and biological activity of isopentenyl diphosphate analogues

A series of analogues of isopentenyl diphosphate (IPP) having a dicarboxylate moiety in place of the diphosphate were synthesized and investigated as inhibitors of undecaprenyl diphosphate (UPP) synthase and protein farnesyltransferase (PFTase). PFTase is involved in control of cell proliferation and is known to be inhibited by certain maleic acid derivatives bearing long alkyl substituents (≥12 carbons, e.g., chaetomellic acid). UPP synthase is a potential target for antimicrobial agents and utilizes isopentenyl diphosphate (IPP) as a substrate. A number of dicarboxylate- containing IPP analogues were prepared in 2-5 steps from commercially available starting materials with good overall yield (20-78%). These syntheses involved the conjugate addition of an organocuprate to dimethyl acetylenedicarboxylate (DMAD) followed by basic ester hydrolysis. The E-pentenylbutanedioic acid 32 showed inhibition of UPP synthase with an IC50 of 135 μM. Compound 30 displays competitive inhibition of PFTase with a Ki of 287 μM.