111057-92-2

Basic information

• Product Name: (7aR,13aR)-6-hydroxy-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one
• CAS NO: 111057-92-2
• Molecular Formula: C₂₃H₂₂O₇
• Molecular Weight: 410.4166
• Mol File: 111057-92-2.mol

Chemical Properties

• Boiling Point: 607.2°C at 760 mmHg
• Flash Point: 213°C
• Density: 1.312g/cm³
• Vapor Pressure: 2.46E-15mmHg at 25°C
• Refractive Index: 1.6
• CAS DataBase Reference: (7aR,13aR)-6-hydroxy-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (7aR,13aR)-6-hydroxy-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one(111057-92-2)
• EPA Substance Registry System: (7aR,13aR)-6-hydroxy-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one(111057-92-2)

Safety Data

• Hazardous Substances Data: 111057-92-2(Hazardous Substances Data)

Upstream product

• 59086-93-0 6a,12a-dehydro-α-toxicarol 
• 82-09-7 alpha-toxicarol 

Downstream Products

• 13133-20-5 cis-α-toxicarol 

Relevant articles and documents

Synthesis of trans-B/C-Rotenoids: X-Ray and NMR Data for cis- and trans-Forms of Isorotenone

Reduction of 6a,12a-didehydrorotenoids with diisobutylaluminium hydride gives clean 1,4-reduction leading to unstable trans-B/C-fusions, not previously known for enolisable rotenoids: they are epimerised to stable cis-forms under acid conditions.Applied initially to isorotenone, the method is extended to trans-B/C-deguelin, α-toxicarol, the 'core' rotenoid structure and the 6aS,12aR,5'R- and 6aR,12aS,5'R-rotenone stereoisomers. 1H and 13C NMR data are compared for the cis- and trans-forms and the geometry and conformations of the isorotenones are compared by X-ray analysis, providing insight into the reasons for the instability of the trans-forms.Reduction of the ridge-tile-like cis-isorotenone by sodium borohydride occurs from one face to give a cis-12α-hydroxy product, whilst the flatter trans-structure is attacked from both faces to give trans-12α- and 12β-hydroxy products.

Synthesis of Novel Labile Rotenoids with Unnatural trans-B/C Ring Systems

6a,12a-Dehydrorotenoids are cleanly reduced in 1,4-fashion by DIBAL to give rotenoids having the unstable, unnatural, trans-B/C fusion, readily epimerised by acid to the cis-forms: an X-ray structure for (+/-)-trans-isorotenone confirms the nature of the ring fusion.