490-31-3

Basic information

• Product Name: ROBINETIN
• Synonyms: ROBINETIN;3,3’,4’,5’,7-pentahydroxy-flavon;3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-4h-1-benzopyran-4-on;norkanugin;3,7,3',4',5'-PENTAHYDROXYFLAVONE;5-HYDROXYFISETIN;3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-4-benzopyrone;3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl-4H-1-benzopyran-4-one) (Robinetin)
• CAS NO: 490-31-3
• Molecular Formula: C₁₅H₁₀O₇
• Molecular Weight: 302.24
• EINECS: 207-709-6
• Product Categories: Flavanols;Penta-substituted Flavones
• Mol File: 490-31-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 326-328°C
• Boiling Point: 363.28°C (rough estimate)
• Flash Point: 258.6 °C
• Appearance: /
• Density: 1.3616 (rough estimate)
• Vapor Pressure: 7.35E-19mmHg at 25°C
• Refractive Index: 1.4790 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Sparingly), Methanol (Slightly, Heated)
• PKA: 6.82±0.40(Predicted)
• CAS DataBase Reference: ROBINETIN(CAS DataBase Reference)
• NIST Chemistry Reference: ROBINETIN(490-31-3)
• EPA Substance Registry System: ROBINETIN(490-31-3)

Safety Data

• Statements: 22
• Safety Statements: 22-45
• RIDADR: 2811
• Hazardous Substances Data: 490-31-3(Hazardous Substances Data)

Usage

Definition

ChEBI: A pentahydroxyflavone that is flavone substituted by hydroxy groups at positions 3, 7, 3, 4' and 5'.

InChI:InChI=1/C15H10O7/c16-7-1-2-8-11(5-7)22-15(14(21)12(8)19)6-3-9(17)13(20)10(18)4-6/h1-5,16-18,20-21H

Synthetic route

7-benzyloxy-3-hydroxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one (354119-95-2) → robinetin (490-31-3)

Conditions	Yield
With boron tribromide In dichloromethane at 20℃; for 22h;	99%

3-Hydroxy-7,3',4',5'-tetramethoxyflavone → robinetin (490-31-3)

Conditions	Yield
With boron tribromide In dichloromethane at 20℃; for 48h; Inert atmosphere;	81%

Robinetin trimethyl ether (132594-09-3) → robinetin (490-31-3)

Conditions	Yield
With hydrogen iodide; acetic anhydride

3,7,3'-trimethoxy-4',5'-dihydroxyflavone (223902-81-6) → robinetin (490-31-3)

Conditions	Yield
With hydrogen iodide; acetic anhydride

7-hydroxy-3-methoxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one (20979-43-5) → robinetin (490-31-3)

Conditions	Yield
With hydrogen iodide; acetic anhydride

Dihydrorobinetin (4382-33-6) → robinetin (490-31-3)

Conditions	Yield
With sulfuric acid Durchleiten von Luft;

1-[4-(benzyloxy)-2-hydroxyphenyl]ethanone (29682-12-0) → robinetin (490-31-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium hydroxide / ethanol / 144 h 2: 84 mg / H2O2; NaOH / tetrahydrofuran; H2O / 47 h / cooling 3: 99 percent / boron tribromide / CH2Cl2 / 22 h / 20 °C View Scheme

2',4'-dihydroxy-4-acetophenone (89-84-9) → robinetin (490-31-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 87 percent / potassium carbonate / acetone / 18 h / Heating 2: potassium hydroxide / ethanol / 144 h 3: 84 mg / H2O2; NaOH / tetrahydrofuran; H2O / 47 h / cooling 4: 99 percent / boron tribromide / CH2Cl2 / 22 h / 20 °C View Scheme

1-(4-benzyloxy-2-hydroxy-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propenone → robinetin (490-31-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 84 mg / H2O2; NaOH / tetrahydrofuran; H2O / 47 h / cooling 2: 99 percent / boron tribromide / CH2Cl2 / 22 h / 20 °C View Scheme

2',4'-dihydroxy-2-methoxyacetophenone (57280-75-8) → robinetin (490-31-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium-<3,4,5-trimethoxy benzoate> / 180 °C / Erwaermen des Reaktionsprodukts mit wss.-aethanol. Kalilauge 2: acetic acid anhydride; aqueous hydriodic acid View Scheme

3,4,5-trimethoxybenzoic anhydride (1719-88-6) → robinetin (490-31-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium-<3,4,5-trimethoxy benzoate> / 180 °C / Erwaermen des Reaktionsprodukts mit wss.-aethanol. Kalilauge 2: acetic acid anhydride; aqueous hydriodic acid View Scheme

3-hydroxy-7-methoxymethoxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one (109980-57-6) → robinetin (490-31-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; aqueous sulfuric acid 2: acetic acid anhydride; aqueous hydriodic acid View Scheme

(E)‐1‐(2‐hydroxy‐4‐methoxyphenyl)‐3‐(3,4,5‐trimethoxyphenyl)prop‐2‐en‐1‐one (13745-26-1, 142955-69-9) → robinetin (490-31-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; dihydrogen peroxide / ethanol; water / 20 °C 2: boron tribromide / dichloromethane / 48 h / 20 °C / Inert atmosphere View Scheme

1-(2-hydroxy-4-methoxyphenyl)ethanone (552-41-0) → robinetin (490-31-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / ethanol / 20 °C 2: sodium hydroxide; dihydrogen peroxide / ethanol; water / 20 °C 3: boron tribromide / dichloromethane / 48 h / 20 °C / Inert atmosphere View Scheme

3,4,5-trimethoxy-benzaldehyde (86-81-7) → robinetin (490-31-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / ethanol / 20 °C 2: sodium hydroxide; dihydrogen peroxide / ethanol; water / 20 °C 3: boron tribromide / dichloromethane / 48 h / 20 °C / Inert atmosphere View Scheme

diazomethane (186581-53-3, 908094-01-9) + robinetin (490-31-3) → 3,7,3',4',5'-O-pentamethylrobinetin (19056-76-9)

Conditions	Yield
With methanol; diethyl ether

robinetin (490-31-3) + acetic anhydride (108-24-7) → 3,7-diacetoxy-2-(3,4,5-triacetoxy-phenyl)-chromen-4-one (73489-98-2)

Conditions	Yield
With pyridine

robinetin (490-31-3) + dimethyl sulfate (77-78-1) → 3,7,3',4',5'-O-pentamethylrobinetin (19056-76-9)

Conditions	Yield
With potassium carbonate; acetone

robinetin (490-31-3) → C15H7O7

Conditions	Yield
With 2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl In methanol at 25℃; Kinetics; Further Variations:; Solvents;

Upstream product

• 132594-09-3 Robinetin trimethyl ether 
• 4382-33-6 Dihydrorobinetin 
• 57280-75-8 2',4'-dihydroxy-2-methoxyacetophenone 
• 1719-88-6 3,4,5-trimethoxybenzoic anhydride 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 13745-26-1 (E)‐1‐(2‐hydroxy‐4‐methoxyphenyl)‐3‐(3,4,5‐trimethoxyphenyl)prop‐2‐en‐1‐one 
• 109980-57-6 3-hydroxy-7-methoxymethoxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 29682-12-0 1-[4-(benzyloxy)-2-hydroxyphenyl]ethanone 
• 223902-81-6 3,7,3'-trimethoxy-4',5'-dihydroxyflavone 
• 354119-95-2 7-benzyloxy-3-hydroxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one 
• 20979-43-5 7-hydroxy-3-methoxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one 

Downstream Products

• 19056-76-9 3,7,3',4',5'-O-pentamethylrobinetin 
• 73489-98-2 3,7-diacetoxy-2-(3,4,5-triacetoxy-phenyl)-chromen-4-one 

Relevant articles and documents

Profiling of flavonol derivatives for the development of antitrypanosomatidic drugs

Flavonoids represent a potential source of new antitrypanosomatidic leads. Starting from a library of natural products, we combined target-based screening on pteridine reductase 1 with phenotypic screening on Trypanosoma brucei for hit identification. Flavonols were identified as hits, and a library of 16 derivatives was synthesized. Twelve compounds showed EC50 values against T. brucei below 10 μM. Four X-ray crystal structures and docking studies explained the observed structure-activity relationships. Compound 2 (3,6-dihydroxy-2-(3-hydroxyphenyl)-4H-chromen-4-one) was selected for pharmacokinetic studies. Encapsulation of compound 2 in PLGA nanoparticles or cyclodextrins resulted in lower in vitro toxicity when compared to the free compound. Combination studies with methotrexate revealed that compound 13 (3-hydroxy-6-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one) has the highest synergistic effect at concentration of 1.3 μM, 11.7-fold dose reduction index and no toxicity toward host cells. Our results provide the basis for further chemical modifications aimed at identifying novel antitrypanosomatidic agents showing higher potency toward PTR1 and increased metabolic stability.