76191-52-1

Basic information

• Product Name: Antibiotic WS 5995B
• Synonyms: Antibiotic WS 5995B;WS-5995 B;2-(1,4-Dihydro-5-hydroxy-1,4-dioxonaphthalen-2-yl)-3-methoxy-5-methylbenzoic acid;6-(1,4-Dioxo-5-hydroxy-1,4-dihydronaphthalene-2-yl)-3-methyl-5-methoxybenzoic acid
• CAS NO: 76191-52-1
• Molecular Formula: C₁₉H₁₄O₆
• Molecular Weight: 338.314
• Mol File: 76191-52-1.mol

Chemical Properties

• Boiling Point: 626.2°C at 760 mmHg
• Flash Point: 231.5°C
• Appearance: /
• Density: 1.433g/cm³
• Vapor Pressure: 1.51E-16mmHg at 25°C
• Refractive Index: 1.665
• CAS DataBase Reference: Antibiotic WS 5995B(CAS DataBase Reference)
• NIST Chemistry Reference: Antibiotic WS 5995B(76191-52-1)
• EPA Substance Registry System: Antibiotic WS 5995B(76191-52-1)

Safety Data

• Hazardous Substances Data: 76191-52-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C19H14O6/c1-9-6-12(19(23)24)16(15(7-9)25-2)11-8-14(21)17-10(18(11)22)4-3-5-13(17)20/h3-8,20H,1-2H3,(H,23,24)

Upstream product

• 125187-17-9 2-2'-carboxy-6'-methoxy-4'-methylphenyl-5-hydroxy-3-phenylthio-1,4-naphthoquinone 
• 125187-10-2 2-2'-carbobenzyloxy-6'-methoxy-4'-methylphenyl-3,5-dichloro-1,4-benzoquinone 
• 125187-13-5 5-acetoxy-2-2'-carbobenzyloxy-6'-methoxy-4'-methylphenyl-3-chloro-1,4-naphthoquinone 
• 125187-11-3 2-2'-carbobenzyloxy-6'-methoxy-4'-methylphenyl-3,4a-dichloro-5,8,8a-trihydro-5-trimethylsilyloxy-1,4-naphthoquinone 
• 125187-15-7 5-acetoxy-2-2'-carboxy-6'-methoxy-4'-methylphenyl-3-chloro-1,4-naphthoquinone 
• 125187-16-8 2-2'-carboxy-6'-methoxy-4'-methylphenyl-3-chloro-5-hydroxy-1,4-naphthoquinone 
• 155722-67-1 3-bromo-2-(2-methoxycarbonyl-6-methoxy-4-methyl)phenyljuglone 
• 1026950-14-0 3-bromo-5,6,7,8-tetrahydrojuglone 
• 147699-89-6 N-acetyl-3-methoxy-5-methyl anthranilic acid 
• 147699-88-5 N-acetyl-2-bromo-6-methoxy p-toluidine 
• 147699-87-4 2-bromo-6-methoxy-p-toluidine 
• 80389-40-8 3-methoxy-5-methyl anthranilic acid 
• 85755-06-2 7-bromo-5,8-dimethoxy-1,2,3,4-tetrahydro-1-naphthol 
• 77199-82-7 7-bromo-5,8-dimethoxy-1-tetralone 

Downstream Products

• 76191-51-0 8-hydroxy-1-methoxy-3-methyl-5H-benzonaphtho<2,3-b>pyran-5,7,12-trione 
• 155722-68-2 2-(2-methoxycarbonyl-6-methoxy-4-methyl)phenyljuglone 

Relevant articles and documents

Synthesis of benzo[b]phenanthridines and related naturally occurring 2-aryl-1,4-naphthoquinones by palladium- and copper-catalyzed coupling of organostannanes with bromoquinones

Syntheses of phenanthroviridone, gilvocarcin BE-12406X2, antibiotic WS 5995B, and a key intermediate for the synthesis of jadomycin are described, based on palladium- and copper-catalyzed coupling reactions of sterically hindered arylstannanes

Syntheses of fenanthroviridone, gilvocarcin BE-12406X2, and antibiotic WS 599B based on the palladium and copper catalyzed coupling of organostannanes with bromoquinones

A total synthesis of fenanthroviridone, gilvocarcin BE-12406X2, antibiotic WS 5995B is described based on the palladium and copper catalyzed coupling reaction of sterically hindered aryl stannanes with a 2-bromonaphthoquinone. Copyright (C) 199

A new convergent synthesis of WS-5995-B, an anticoccidial antibiotic from Streptomyces auranticolor

A new synthesis of WS-5995-B, an anticoccidial antibiotic isolated from Streptomyces auranticolor is reported via the coupling reaction between 3-bromo-5,6,7,8-tetrahydrojuglone, and 3-methoxy-5-methyl anthranilic acid. A simple method for the preparation of the anthranilate 7 starting from p-toluidine by shorter sequence is reported.

THE TOTAL SYNTHESIS OF THE ANTI-COCCIDIAL AGENTS WS-5995

A total synthesis of the three anti-coccidial agents WS-5995 A, B, and C by a Diels-Alder route is described.An intramolecular lactonization involving the displacement of a chlorine atom on a napthoquinone was the key step in the synthesis of A.

1,4-Naphtoquinone derivatives and their use in treating coccidiosis

1,4-naphthoquinone derivatives represented by the following general formula: STR1 (wherein R1 represents a hydrogen atom, a hydroxy group, a lower alkoxy group or an arylthio group, R2 represents a carboxy group, an esterified carbox