| 
                                    
                                        gptkbp:instanceOf
                                    
                                 | 
                                
                                    
                                        
                                            gptkb:chemical_compound
                                        
                                         
                                    
                                        
                                            gptkb:aromatic_ketone
                                        
                                         
                                    
                                 | 
                            
                        
                            
                                | 
                                    
                                        gptkbp:boilingPoint
                                    
                                 | 
                                
                                    
                                        
                                            
                                            379 °C
                                        
                                        
                                         
                                    
                                 | 
                            
                        
                            
                                | 
                                    
                                        gptkbp:CASNumber
                                    
                                 | 
                                
                                    
                                        
                                            
                                            84-65-1
                                        
                                        
                                         
                                    
                                 | 
                            
                        
                            
                                | 
                                    
                                        gptkbp:category
                                    
                                 | 
                                
                                    
                                        
                                            
                                            natural products
                                        
                                        
                                         
                                    
                                        
                                            
                                            quinones
                                        
                                        
                                         
                                    
                                        
                                            
                                            polycyclic aromatic compounds
                                        
                                        
                                         
                                    
                                 | 
                            
                        
                            
                                | 
                                    
                                        gptkbp:chemicalFormula
                                    
                                 | 
                                
                                    
                                        
                                            
                                            C14H8O2
                                        
                                        
                                         
                                    
                                 | 
                            
                        
                            
                                | 
                                    
                                        gptkbp:color
                                    
                                 | 
                                
                                    
                                        
                                            gptkb:orange
                                        
                                         
                                    
                                        
                                            
                                            red
                                        
                                        
                                         
                                    
                                        
                                            
                                            yellow
                                        
                                        
                                         
                                    
                                 | 
                            
                        
                            
                                | 
                                    
                                        gptkbp:core_structure_of
                                    
                                 | 
                                
                                    
                                        
                                            
                                            alizarin
                                        
                                        
                                         
                                    
                                        
                                            
                                            emodin
                                        
                                        
                                         
                                    
                                        
                                            
                                            phthalic anhydride
                                        
                                        
                                         
                                    
                                        
                                            
                                            rhein
                                        
                                        
                                         
                                    
                                        
                                            
                                            purpurin
                                        
                                        
                                         
                                    
                                        
                                            
                                            chrysophanol
                                        
                                        
                                         
                                    
                                        
                                            
                                            danthron
                                        
                                        
                                         
                                    
                                        
                                            
                                            quinizarin
                                        
                                        
                                         
                                    
                                 | 
                            
                        
                            
                                | 
                                    
                                        gptkbp:derivative_of
                                    
                                 | 
                                
                                    
                                        
                                            gptkb:anthracene
                                        
                                         
                                    
                                 | 
                            
                        
                            
                                | 
                                    
                                        gptkbp:firstSynthesized
                                    
                                 | 
                                
                                    
                                        
                                            gptkb:August_Wilhelm_von_Hofmann
                                        
                                         
                                    
                                        
                                            
                                            1868
                                        
                                        
                                         
                                    
                                 | 
                            
                        
                            
                                | 
                                    
                                        gptkbp:foundIn
                                    
                                 | 
                                
                                    
                                        
                                            
                                            fungi
                                        
                                        
                                         
                                    
                                        
                                            
                                            lichens
                                        
                                        
                                         
                                    
                                        
                                            
                                            plants
                                        
                                        
                                         
                                    
                                 | 
                            
                        
                            
                                | 
                                    
                                        gptkbp:IUPACName
                                    
                                 | 
                                
                                    
                                        
                                            
                                            9,10-anthracenedione
                                        
                                        
                                         
                                    
                                 | 
                            
                        
                            
                                | 
                                    
                                        gptkbp:meltingPoint
                                    
                                 | 
                                
                                    
                                        
                                            
                                            286 °C
                                        
                                        
                                         
                                    
                                 | 
                            
                        
                            
                                | 
                                    
                                        gptkbp:metabolism
                                    
                                 | 
                                
                                    
                                        
                                            
                                            gut bacteria
                                        
                                        
                                         
                                    
                                 | 
                            
                        
                            
                                | 
                                    
                                        gptkbp:molecularWeight
                                    
                                 | 
                                
                                    
                                        
                                            
                                            208.21 g/mol
                                        
                                        
                                         
                                    
                                 | 
                            
                        
                            
                                | 
                                    
                                        gptkbp:parent
                                    
                                 | 
                                
                                    
                                        
                                            
                                            many natural dyes
                                        
                                        
                                         
                                    
                                 | 
                            
                        
                            
                                | 
                                    
                                        gptkbp:solubility
                                    
                                 | 
                                
                                    
                                        
                                            
                                            slightly soluble in water
                                        
                                        
                                         
                                    
                                        
                                            
                                            soluble in organic solvents
                                        
                                        
                                         
                                    
                                 | 
                            
                        
                            
                                | 
                                    
                                        gptkbp:toxicity
                                    
                                 | 
                                
                                    
                                        
                                            
                                            animals in high doses
                                        
                                        
                                         
                                    
                                        
                                            
                                            humans in high doses
                                        
                                        
                                         
                                    
                                 | 
                            
                        
                            
                                | 
                                    
                                        gptkbp:used_in
                                    
                                 | 
                                
                                    
                                        
                                            
                                            pulp and paper industry
                                        
                                        
                                         
                                    
                                        
                                            
                                            dye manufacturing
                                        
                                        
                                         
                                    
                                 | 
                            
                        
                            
                                | 
                                    
                                        gptkbp:usedFor
                                    
                                 | 
                                
                                    
                                        
                                            gptkb:antioxidant
                                        
                                         
                                    
                                        
                                            gptkb:antiviral_drug
                                        
                                         
                                    
                                        
                                            gptkb:antifungal_agent
                                        
                                         
                                    
                                        
                                            gptkb:entomologist
                                        
                                         
                                    
                                        
                                            gptkb:antibiotic
                                        
                                         
                                    
                                        
                                            gptkb:herbicide
                                        
                                         
                                    
                                        
                                            
                                            intermediate in chemical synthesis
                                        
                                        
                                         
                                    
                                        
                                            
                                            anticancer agent
                                        
                                        
                                         
                                    
                                        
                                            
                                            laxatives
                                        
                                        
                                         
                                    
                                        
                                            
                                            molluscicide
                                        
                                        
                                         
                                    
                                        
                                            
                                            bird repellent
                                        
                                        
                                         
                                    
                                 | 
                            
                        
                            
                                | 
                                    
                                        gptkbp:bfsParent
                                    
                                 | 
                                
                                    
                                        
                                            gptkb:Aloes
                                        
                                         
                                    
                                 | 
                            
                        
                            
                                | 
                                    
                                        gptkbp:bfsLayer
                                    
                                 | 
                                
                                    
                                        
                                            
                                            8
                                        
                                        
                                         
                                    
                                 | 
                            
                        
                            
                                | 
                                    
                                        https://www.w3.org/2000/01/rdf-schema#label
                                    
                                 | 
                                
                                    
                                        
                                            
                                            Anthraquinones
                                        
                                        
                                         
                                    
                                 |