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

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

Uses

Used in Pharmaceutical Industry:
5-HYDROXYDEQUELIN is used as an antimicrobial agent for its potential to treat infections caused by multi-drug resistant bacteria. Its unique properties allow it to target and inhibit the growth of these bacteria, providing a potential solution to the growing problem of antibiotic resistance.
5-HYDROXYDEQUELIN is also used as an antifungal agent for its ability to inhibit the growth of certain strains of yeast. This application can be beneficial in the development of new treatments for fungal infections, which can be challenging to manage with existing antifungal drugs.
Furthermore, 5-HYDROXYDEQUELIN is used in the research and development of new pharmaceuticals for treating various infectious diseases. Its potential applications in this area are still being explored, and further research is needed to fully understand its mechanisms and potential uses in this field.

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

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

Downstream Products

• 82-09-7 (+/-)-trans-α-toxicarol 
• 13133-20-5 cis-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 
• 54388-93-1 (-)-Dihydro-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.

DEGUELIN CYCLASE, A PRENYL TO CHROMEN TRANSFORMING ENZYME FROM TEPHROSIA VOGELLII

Seeds and plant parts of Tephrosia vogellii were investigated in order to provide systems for the study of prenyl to chromen transformation in rotenoids, as exemplified by the conversion of rot-2-enonic acid into deguelin.No hydroxylated intermediate was found.A cell free preparation has been obtained from T. vogellii seedlings or seeds and shown to catalyse the reaction.The water soluble enzyme has been partially purified using ammonium sulphate precipitation, gel chromatography and ion exchange procedures.Data for the enzyme named degueline cyclase, are reported - optima for pH and temperature and Km (which indicates strong binding between enzyme and substrate).Results relevant to Mr determination are discussed.The enzyme has a requirement for oxygen, but not for cofactors.It is inhibited by chloride ion and chelating agents, particularly 1,10-phenanthroline.Deguelin cyclase can convert the 11-hydroxyrotenoid sumatrolic acid into α-toxicarol and lapachol into dehydro-α-lapachone, though the prenyl to chromen conversion is not general.It does not convert rot-2'-enonic acid into rotenone under the conditions studied.Deguelin cyclase seems not to belong to the P450 group and resembles more closely the non-heme iron protein isopenicillin N synthase. Key words: Tephrosia vogellii; Leguminosae; rotenoids; biosynthesis; deguelin; rot-2'-enonic acid; deguelin cyclase; enzyme isolation; enzyme properties.

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.