484-29-7

Basic information

• Product Name: DICTAMNINE
• Synonyms: DICTAMNINE;3-b)quinoline,4-methoxy-furo(;dictamine;4-Methoxyfuro[2,3-b]quinoline;Dictamnine ,98%;Dictamnine 4-Methoxyfuro[2,3-b]quinoline
• CAS NO: 484-29-7
• Molecular Formula: C₁₂H₉NO₂
• Molecular Weight: 199.21
• Product Categories: Miscellaneous Natural Products;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 484-29-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 133°
• Boiling Point: 336.72°C (rough estimate)
• Flash Point: 161.387 °C
• Appearance: /
• Density: 1.1919 (rough estimate)
• Vapor Pressure: 0.000142mmHg at 25°C
• Refractive Index: 1.5880 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly, Heated)
• PKA: 7.24±0.40(Predicted)
• CAS DataBase Reference: DICTAMNINE(CAS DataBase Reference)
• NIST Chemistry Reference: DICTAMNINE(484-29-7)
• EPA Substance Registry System: DICTAMNINE(484-29-7)

Safety Data

• Hazardous Substances Data: 484-29-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 484-29-7 differently. You can refer to the following data:
1. antifungal, vasal relaxant, mooth muscle contractant
2. Dictamnine is an herbal extract from the root of Dictamnus dasycarpus, and exhibits anti-microbial activity against bacteria and fungi. Phytotoxic agent.

Synthesis Reference(s)

Tetrahedron Letters, 14, p. 843, 1973 DOI: 10.1016/S0040-4039(01)95731-4

InChI:InChI=1/C12H9NO2/c1-14-11-8-4-2-3-5-10(8)13-12-9(11)6-7-15-12/h2-7H,1H3

Upstream product

• 111163-82-7 4-chlorofuro[2,3-b]quinoline 
• 63536-51-6 4-chloro-2,3-dihydro-furo[2,3-b]quinoline 
• 112071-08-6 3-chloro-4-methoxy-furo[2,3-b]quinoline 
• 51179-18-1 2,4-dimethoxy-3-formylquinoline 
• 2181-42-2 trimethylsulphonium iodide 
• 60623-06-5 trans-2,3-dihydro-3-hydroxy-4-methoxy-α,α-dimethylfuro[2,3-b]quinoline-2-methanol 
• 38975-98-3 (2-hydroxy-4-methoxy-quinolin-3-yl)acetaldehyde 
• 67-56-1 methanol 
• 40335-00-0 2,4-dimethoxyquinoline 
• 827303-64-0 2,4-dimethoxy-3-oxiranylquinoline 
• 111736-15-3 3-(2,2-dichloroethyl)-4-methoxy-2-quinolone 
• 110744-47-3 2-(Trimethylsilyl)dictamnin 
• 95874-16-1 4-ethoxy-furo[2,3-b]quinoline 
• 16251-56-2 4-methoxy-2,3-dihydrofuro[2,3-b]quinoline 

Downstream Products

• 484-74-2 iso-dictamnine 
• 530-52-9 furo[2,3-b]quinolin-4(9H)-one 
• 523-61-5 Dictaminsaeure 
• 530-52-9 nordictamnine 
• 2255-50-7 robustine 
• 524-15-2 4,8-dimethoxyfuro[2,3-b]quinoline 
• 2221-41-2 pteleine 
• 627086-17-3 4-chlorofuro[3,2-c]quinoline 

Relevant articles and documents

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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.

Synthesis of (+)-myrtopsine, (+)-7,8-dimethoxymyrtopsine, and related 2,3-dihydro-3-hydroxy-2-(1-hydroxy-1-methyl-ethyl)benzofuran natural products

The first syntheses of myrtopsine (8t) and 7,8-dimethoxymyrtopsine (9t) have been carried out by halogen-metal exchange of 3-iodo-4-methoxy-quinolin-2(1H)-ones (15) and (21) with i-PrMgCl followed by addition of 3,3-dimethyloxirane-2-carboxaldehyde (1). A two-step sequence leads selectively to trans-2,3-dihydro-3-hydroxy-2-(1-hydroxy-1-methylethyl)benzofurans (7t), (8t), (9t), (28), and (32) by conversion of a 2-iodophenol or a 3-iodo-4-methoxyquinolin-2(1H)-one to an aryl Grignard reagent and addition of 3-methyl-2-butenal, followed by threo selective epoxidation of the resulting allylic alcohol and cyclization with inversion.