13133-20-5

Basic information

• Product Name: cis-α-toxicarol
• Synonyms: cis-α-toxicarol
• CAS NO: 13133-20-5
• Molecular Weight: 410.423
• Mol File: 13133-20-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: cis-α-toxicarol(CAS DataBase Reference)
• NIST Chemistry Reference: cis-α-toxicarol(13133-20-5)
• EPA Substance Registry System: cis-α-toxicarol(13133-20-5)

Safety Data

• Hazardous Substances Data: 13133-20-5(Hazardous Substances Data)

Upstream product

• 82-09-7 alpha-toxicarol 
• 59086-93-0 6a,12a-dehydro-α-toxicarol 
• 82-09-7 (+/-)-trans-α-toxicarol 

Downstream Products

• 13122-02-6 (+/-)-13-hydroxy-2,3-dimethoxy-10,10-dimethyl-(6ar,14ac)-6a,14a-dihydro-6H,10H-pyrano[2,3-c;5,6-g'] dichromium en-14-one 

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.