82-09-7

Basic information

• Product Name: 5-HYDROXYDEQUELIN
• Synonyms: TOXICAROL;5-HYDROXYDEQUELIN;(7aS)-13,13aα-Dihydro-6-hydroxy-9,10-dimethoxy-3,3-dimethyl-3H-bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7(7aαH)-one;(7aS,13aS)-13,13a-Dihydro-6-hydroxy-9,10-dimethoxy-3,3-dimethyl-3H-bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7(7aH)-one;alpha-Toxicarol
• CAS NO: 82-09-7
• Molecular Formula: C₂₃H₂₂O₇
• Molecular Weight: 410.42
• Product Categories: Miscellaneous Natural Products
• Mol File: 82-09-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 222℃
• Boiling Point: 607.2 °C at 760 mmHg
• Flash Point: 213 °C
• Appearance: /
• Density: 1.312 g/cm³
• Vapor Pressure: 2.46E-15mmHg at 25°C
• Refractive Index: >1.768
• CAS DataBase Reference: 5-HYDROXYDEQUELIN(CAS DataBase Reference)
• NIST Chemistry Reference: 5-HYDROXYDEQUELIN(82-09-7)
• EPA Substance Registry System: 5-HYDROXYDEQUELIN(82-09-7)

Safety Data

• Hazardous Substances Data: 82-09-7(Hazardous Substances Data)

Usage

General Description

5-HYDROXYDEQUELIN is a chemical compound that belongs to the quinoline family. It is a derivative of dequalinium, a quaternary ammonium compound with antiseptic properties. This chemical has been studied for its potential use as an antimicrobial agent, particularly as a treatment for infections caused by multi-drug resistant bacteria. 5-HYDROXYDEQUELIN has also been investigated for its antifungal properties and its potential to inhibit the growth of certain strains of yeast. It may have applications in the development of new pharmaceuticals for treating various infectious diseases. Further research is needed to fully understand the potential uses and mechanisms of this chemical compound.

InChI:InChI=1/C23H22O7/c1-23(2)6-5-11-15(30-23)8-13(24)20-21(25)19-12-7-16(26-3)17(27-4)9-14(12)28-10-18(19)29-22(11)20/h5-9,18-19,24H,10H2,1-4H3/t18-,19?/m1/s1

Upstream product

• 139664-41-8 Sumatrolic acid 
• 82-10-0 sumatrol 
• 59086-93-0 6a,12a-dehydro-α-toxicarol 

Downstream Products

• 54388-93-1 (-)-Dihydro-α-toxicarol 
• 13133-20-5 cis-α-toxicarol 
• 82-09-7 (+/-)-trans-α-toxicarol 
• 54388-93-1 (+/-)-Dihydro-α-toxicarol 
• 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 
• 59086-93-0 6a,12a-dehydro-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.