22489-66-3

Basic information

• Product Name: (3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-9-methyl-3,6-dimethylideneoctahydroazuleno[4,5-b]furan-2,8(3H,4H)-dione
• Synonyms: (3aR-(3aa,4a,6aa,9a,9aa,9bb))-Octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)azuleno[4,5-b]furan-2,8(3H,4H)-dione; (3aR,4S,6aR,9S,9aR,9bR)-4-Hydroxy-9-methyl-3,6-bis(methylene)octahydroazuleno[4,5-b]furan-2,8(3H,4H)-dione; 22489-66-3; azuleno[4,5-b]furan-2,8(3H,4H)-dione, octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR,4S,6aR,9S,9aR,9bR)-
• CAS NO: 22489-66-3
• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.301
• Mol File: 22489-66-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 480.7°C at 760 mmHg
• Flash Point: 183.2°C
• Density: 1.24g/cm³
• Vapor Pressure: 2.93E-11mmHg at 25°C
• Refractive Index: 1.554
• CAS DataBase Reference: (3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-9-methyl-3,6-dimethylideneoctahydroazuleno[4,5-b]furan-2,8(3H,4H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-9-methyl-3,6-dimethylideneoctahydroazuleno[4,5-b]furan-2,8(3H,4H)-dione(22489-66-3)
• EPA Substance Registry System: (3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-9-methyl-3,6-dimethylideneoctahydroazuleno[4,5-b]furan-2,8(3H,4H)-dione(22489-66-3)

Safety Data

• Hazardous Substances Data: 22489-66-3(Hazardous Substances Data)

Usage

General Description

The chemical "(3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-9-methyl-3,6-dimethylideneoctahydroazuleno[4,5-b]furan-2,8(3H,4H)-dione" is a complex organic compound with a fused furan and lactone ring structure. It has a molecular formula of C15H18O4 and a molecular weight of 262.3 g/mol. This chemical is a naturally occurring compound and is found in certain plants. Its exact biological activity and potential applications are not well-established, but its unique structure suggests that it may have potential pharmaceutical or medicinal properties. Further research is needed to understand its role and applications in various fields.

Upstream product

• 248584-41-0 N-[4-((3S,3aR,4S,6aR,9S,9aR,9bR)-4-Hydroxy-9-methyl-6-methylene-2,8-dioxo-dodecahydro-azuleno[4,5-b]furan-3-ylmethylsulfanyl)-phenyl]-acetamide 
• 248584-42-1 (3S,3aR,4S,6aR,9S,9aR,9bR)-4-Hydroxy-3-(4-methoxy-phenylsulfanylmethyl)-9-methyl-6-methylene-octahydro-azuleno[4,5-b]furan-2,8-dione 
• 248584-38-5 (3S,3aR,4S,6aR,9S,9aR,9bR)-4-Hydroxy-9-methyl-6-methylene-3-m-tolylsulfanylmethyl-octahydro-azuleno[4,5-b]furan-2,8-dione 
• 248584-40-9 (3S,3aR,4S,6aR,9S,9aR,9bR)-4-Hydroxy-9-methyl-6-methylene-3-phenylsulfanylmethyl-octahydro-azuleno[4,5-b]furan-2,8-dione 
• 100187-62-0 crepiside D 
• 84305-03-3 grosheiminol 
• 248584-37-4 (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 
• 248584-39-6 (3S,3aR,4S,6aR,9S,9aR,9bR)-4-Hydroxy-9-methyl-6-methylene-3-o-tolylsulfanylmethyl-octahydro-azuleno[4,5-b]furan-2,8-dione 
• 248584-43-2 (3S,3aR,4S,6aR,9S,9aR,9bR)-4-Hydroxy-3-(3-methoxy-phenylsulfanylmethyl)-9-methyl-6-methylene-octahydro-azuleno[4,5-b]furan-2,8-dione 
• 248584-44-3 (3S,3aR,4S,6aR,9S,9aR,9bR)-4-Hydroxy-3-(2-methoxy-phenylsulfanylmethyl)-9-methyl-6-methylene-octahydro-azuleno[4,5-b]furan-2,8-dione 

Downstream Products

• 125403-32-9 11-H-13-Se-phenyl grosheimin 
• 125403-31-8 11-H, 13-ethoxy grosheimin 
• 518034-55-4 cynarascolide 
• 84305-03-3 grosheiminol 
• 248584-40-9 (3S,3aR,4S,6aR,9S,9aR,9bR)-4-Hydroxy-9-methyl-6-methylene-3-phenylsulfanylmethyl-octahydro-azuleno[4,5-b]furan-2,8-dione 
• 248584-37-4 (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 

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.

SESQUITERPENIC LACTONES FROM Grossheimia macrocephala. STRUCTURE OF GROSHEIMINOL

From the leaves of Grossheimia macrocephala (MUSS.-PUSCHK.) D.SOSN. et TAKHT. cynaropicrin (II), isolipidiol (III) and the so far undescribed lactone grosheiminol (IV) were isolated in addition to grosheimin (I), detected in this species earlier.For grosheiminol the structure IV was derived, including relative and absolute configuration, on the basis of chemical correlation.