549-22-4

Basic information

• Product Name: (6aS,12aS)-8,9-dimethoxy-2-(1-methylethyl)-12,12a-dihydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one
• Synonyms: (1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one, 12,12a-dihydro-8,9-dimethoxy-2-(1-methylethyl)-, (6aS-cis)-
• CAS NO: 549-22-4
• Molecular Formula: C₂₃H₂₂O₆
• Molecular Weight: 394.4172
• Mol File: 549-22-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 184 °C
• Boiling Point: 530.1°C at 760 mmHg
• Flash Point: 274.4°C
• Density: 1.265g/cm³
• Vapor Pressure: 2.54E-11mmHg at 25°C
• Refractive Index: 1.6
• CAS DataBase Reference: (6aS,12aS)-8,9-dimethoxy-2-(1-methylethyl)-12,12a-dihydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (6aS,12aS)-8,9-dimethoxy-2-(1-methylethyl)-12,12a-dihydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one(549-22-4)
• EPA Substance Registry System: (6aS,12aS)-8,9-dimethoxy-2-(1-methylethyl)-12,12a-dihydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one(549-22-4)

Safety Data

• Hazardous Substances Data: 549-22-4(Hazardous Substances Data)

Upstream product

• 83-79-4 rotenone 
• 3466-09-9 6a,12a-dehydrorotenone 
• 123000-20-4 (6aS,12aR,5'R)-(trans)-(+)-rotenone 
• 5740-14-7 6a,12a-didehydroisorotenone 
• 144849-49-0 O-Ethoxycarbonylmethyl Isoderritol Isoflavone 
• 144849-56-9 O-Carboxymethyl Isoderritol Isoflavone 
• 1026433-52-2 [2-(8-Isopropyl-4-oxo-4H-furo[2,3-h]chromen-3-yl)-4,5-dimethoxy-phenoxy]-acetyl chloride 
• 27337-57-1 7-(2-hydroxy-4,5-dimethoxyphenyl)-2-isopropylfuro<2,3-h>benzopyran-6-one 
• 58137-37-4 O-allylisoderritol isoflavone 
• 125092-50-4 [2-(8-Isopropyl-4-oxo-4H-furo[2,3-h]chromen-3-yl)-4,5-dimethoxy-phenoxy]-acetic acid 2-thioxo-2H-pyridin-1-yl ester 
• 549-22-4 (+/-)-trans-isorotenone 
• 24946-59-6 6aα,12aα-rotenone 
• 30462-22-7 2-((2R,6aS,12aS)-8,9-dimethoxy-1,2,6,6a,12,12a-hexahydrochromeno[3,4-b]furo[2,3-h]chromen-2-yl)propan-2-ol 
• 870-63-3 prenyl bromide 

Downstream Products

• 29609-61-8 (+/-)-Isorotenolon-A 
• 29609-61-8 (+/-)-Isorotenolon-B 
• 549-22-4 (+/-)-cis-isorotenone 
• 4970-30-3 {2-[2-(4-hydroxy-2-isopropyl-benzofuran-5-yl)-2-oxo-ethyl]-4,5-dimethoxy-phenoxy}-acetic acid 
• 103674-04-0 (+/-)-Isorotenolon-A-methylaether 
• 103674-04-0 (+/-)-Isorotenolon B-methylaether 

Relevant articles and documents

General Synthetic Approach to Rotenoids via Stereospecific, Group-Selective 1,2-Rearrangement and Dual S N Ar Cyclizations of Aryl Fluorides

A general synthetic approach to rotenoids is described, featuring 1) stereospecific, group-selective 1,2-rearrangements of epoxy alcohols, and 2) S N Ar oxy-cyclizations of aryl fluorides. The common intermediate epoxyketone, en route to (-)-rotenone and (-)-deguelin, was prepared from d -araboascorbic acid in five steps. Also described is the conversion of (-)-deguelin into oxidized congeners, (-)-tephrosin and (+)-12a- epi -tephrosin.

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.