92013-82-6

Basic information

• Product Name: 2,5-Pyrrolidinedione, 3-(4-hydroxypentylidene)-, (E)-
• CAS NO: 92013-82-6
• Molecular Formula: C9H13NO3
• Molecular Weight: 183.207
• Mol File: 92013-82-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2,5-Pyrrolidinedione, 3-(4-hydroxypentylidene)-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Pyrrolidinedione, 3-(4-hydroxypentylidene)-, (E)-(92013-82-6)
• EPA Substance Registry System: 2,5-Pyrrolidinedione, 3-(4-hydroxypentylidene)-, (E)-(92013-82-6)

Safety Data

• Hazardous Substances Data: 92013-82-6(Hazardous Substances Data)

Usage

Class

Lactams (a type of organic compound)

Usage

Reagent in organic synthesis, potential use in pharmaceuticals and natural health products

Biological activity

Potential for pharmaceutical and health product applications

Antioxidant properties

Investigated for potential benefits in skin and hair care products

Upstream product

• 18545-25-0 5-methyl-tetrahydro-furan-2-ol 
• 18092-16-5 triphenylphosphoranylidene succinimide 

Downstream Products

• 100017-03-6 3(S(R))-<5(R(S))-methyl-2(S(R))-tetrahydrofuryl>-3-(phenylselenyl)-2,5-pyrrolidinedione 

Relevant articles and documents

Two Total Syntheses of Showdomycin and Related Studies

After a series of model reactions, D-ribose (2) was reacted with 3-(triphenylphosphoranylidene)-2,5-pyrrolidinedione (8a) in THF at reflux to produce 3(E)-2(S),3(S),4(R),5-tetrahydroxy-1-pentylidene)-2,5-pyrrolidinedione (35) (75 percent).Subsequent cyclization of 35 using phenylselenyl chloride followed by hydrogen peroxide gave showdomycin (1) (13 percent) and epi-showdomycin (36) (41 percent).Using a similar strategy 2,3-O-isopropylidene-D-ribose (37b) was reacted sequentially with 1-(triphenylmethyl)-3-(triphenylphosphoranylidene)-2,5-pyrrolidinedione (8b), phenylselenyl chloride, hydrogen peroxide, and trifluoroacetic acid to give (1) (3 percent overall).