248584-37-4

Basic information

• Product Name: (3S,3aR,4S,6aR,9S,9aR,9bR)-4-Hydroxy-9-methyl-6-methylene-3-p-tolylsulfanylmethyl-octahydro-azuleno[4,5-b]furan-2,8-dione
• Synonyms: (3S,3aR,4S,6aR,9S,9aR,9bR)-4-Hydroxy-9-methyl-6-methylene-3-p-tolylsulfanylmethyl-octahydro-azuleno[4,5-b]furan-2,8-dione
• CAS NO: 248584-37-4
• Molecular Weight: 386.512
• Mol File: 248584-37-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3S,3aR,4S,6aR,9S,9aR,9bR)-4-Hydroxy-9-methyl-6-methylene-3-p-tolylsulfanylmethyl-octahydro-azuleno[4,5-b]furan-2,8-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,3aR,4S,6aR,9S,9aR,9bR)-4-Hydroxy-9-methyl-6-methylene-3-p-tolylsulfanylmethyl-octahydro-azuleno[4,5-b]furan-2,8-dione(248584-37-4)
• EPA Substance Registry System: (3S,3aR,4S,6aR,9S,9aR,9bR)-4-Hydroxy-9-methyl-6-methylene-3-p-tolylsulfanylmethyl-octahydro-azuleno[4,5-b]furan-2,8-dione(248584-37-4)

Safety Data

• Hazardous Substances Data: 248584-37-4(Hazardous Substances Data)

Upstream product

• 22489-66-3 grosheimin 
• 106-45-6 para-thiocresol 

Downstream Products

• 22489-66-3 grosheimin 
• 106-45-6 para-thiocresol 
• 104-15-4 toluene-4-sulfonic acid 

Relevant articles and documents

Phenylthio-derivatives of α-methylene-γ-lactones as pro-drugs of cytotoxic agents

A series of substituted phenylthio-derivatives of grosheimin (1), a natural cytotoxic guaianolide, were investigated with the aim of providing insight into their mechanism of action as cytotoxic agents against KB cell lines. Hydrolysis data, kinetics, in the presence and in the absence of H2O2, and the valuation of lipophilicity were correlated with cytotoxicity values and with Hammett-σ-values of substituents (R) at the thiophenol ring. These compounds behave as 'pro-drugs' which release the cytotoxic agent grosheimin by sulphur-oxidation promoted by H2O2 and subsequent retro- elimination which depends on the nature and position of the R substituent.