5876-17-5

Basic information

• Product Name: 4,8-Dimethoxyfuro[2,3-b]quinolin-7-ol
• Synonyms: 4,8-Dimethoxyfuro[2,3-b]quinolin-7-ol;Haplopine;Furo(2,3-B)quinolin-7-ol, 4,8-dimethoxy-;Heliparvifoline;7-Hydroxy-8-methoxydictamnine
• CAS NO: 5876-17-5
• Molecular Formula: C₁₃H₁₁NO₄
• Molecular Weight: 245.2307
• Mol File: 5876-17-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 202-204 °C
• Boiling Point: 545.8°Cat760mmHg
• Flash Point: 283.9°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 5.74E-12mmHg at 25°C
• Refractive Index: 1.621
• PKA: 5.60±0.30(Predicted)
• CAS DataBase Reference: 4,8-Dimethoxyfuro[2,3-b]quinolin-7-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 4,8-Dimethoxyfuro[2,3-b]quinolin-7-ol(5876-17-5)
• EPA Substance Registry System: 4,8-Dimethoxyfuro[2,3-b]quinolin-7-ol(5876-17-5)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• Hazardous Substances Data: 5876-17-5(Hazardous Substances Data)

Usage

Description

A further Haplophyllum alkaloid, this base occurs in H. perforatum (MB) Kar. et Kir. and in H. robustum Bge. It crystallizes as small colourless needles from MeOH and has been characterized as the crystalline hydrochloride, m.p. 168- 9°C. The base may be isomerized to isohaplopine, which forms colourless rods from MeOH with m.p. 170-2°C.

References

Sidyakin, Yunusov, Dokl. Akad. Nauk. Uzbek SSR, 4, 39 (1962) Fakhritdinova, Sidyakin, Yunusov,Khim.Prir. Soedin., 1, 107 (1965)

InChI:InChI=1/C13H11NO4/c1-16-11-7-3-4-9(15)12(17-2)10(7)14-13-8(11)5-6-18-13/h3-6,14H,1-2H3

Upstream product

• 115345-33-0 haplosinine 
• 186581-53-3 diazomethane 
• 119188-51-1 4-methoxyfuro[2,3-b]quinoline-7,8-diol 
• 55740-46-0 4,8-dimethoxy-furo[2,3-b]quinolin-7-yl tri-O-acetyl-α-L-6-deoxy-mannopyranoside 
• 865878-27-9 4-chloro-7,8-dimethoxy-furo[2,3-b]quinoline 
• 865878-14-4 (7S,8R)-4-methoxy-7,8-dihydrofuro[2,3-b]quinoline-7,8-diol 
• 107783-37-9 haplobine 
• 58480-58-3 acetylhaplatine 
• 56775-80-5 7-(2'-hydroxy-3'-methoxy-prenyloxy)-4,8-dimethoxyfuroquinoline 
• 52336-91-1 7-benzyloxy-4,8-dimethoxy-furo[2,3-b]quinoline 
• 58480-57-2 4-(4,8-dimethoxy-furo[2,3-b]quinolin-7-yloxy)-2-methyl-but-2-en-1-ol 
• 110548-95-3 evoxine 
• 115345-32-9 haplosidine 
• 83-95-4 skimmianine 

Downstream Products

• 482-32-6 kokusagine 
• 23417-92-7 7-isopentenyloxy-γ-fagarine 
• 83-95-4 skimmianine 
• 5876-30-2 O-(3,4,5-trimethoxybenzoyl)haplopine 

Relevant articles and documents

Biphenyl dioxygenase-catalysed cis-dihydroxylation of tricyclic azaarenes: Chemoenzymatic synthesis of arene oxide metabolites and furoquinoline alkaloids

Biotransformation of acridine, dictamnine and 4-chlorofuro[2,3-b]quinolone, using whole cells of Sphingomonas yanoikuyae B8/36, yielded five enantiopure cyclic cis-dihydrodiols, from biphenyl dioxygenase-catalysed dihydroxylation of the carbocyclic rings.

STRUCTURE OF HAPLOSIDINE

A new glycoalkaloid, haplosidine, has been isolated from the epigeal part of the plant Haplophyllum perforatum, and its structure has been established as 7- 3)-2'-O-acetyl-α-L-rhamnopyranosyloxy>-4,8-dimethoxyfuranoquinoline.

ALKALOIDS OF THE ROOTS OF THE Haplophyllum obtusifolium

The roots of the Haplophyllum obtusifolium Lebed. have been yielded robustine, dictamnine, skimmianine, γ-fagarine, and evoxine and the new alkaloid haplobine for which on the basis of spectral characteristics and a passage to the main alkaloid haplopine (7-hydroxy-4,8-dimethoxylfuranoquinoline) the structure of 7-(3'-chloromethylbut-2'-enyloxy)-4,8-dimethoxyfuranoquinoline has been established.