520-31-0

Basic information

• Product Name: Tricetin
• Synonyms: TRICETIN WITH HPLC;5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one;TRICETIN(SH)
• CAS NO: 520-31-0
• Molecular Formula: C₁₅H₁₀O₇
• Molecular Weight: 302.2357
• Product Categories: Penta-substituted Flavones
• Mol File: 520-31-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: >330 °C (decomp)
• Boiling Point: 721.7 °C at 760 mmHg
• Flash Point: 277.9 °C
• Appearance: /
• Density: 1.763 g/cm³
• Vapor Pressure: 1.61E-21mmHg at 25°C
• Refractive Index: 1.804
• PKA: 6.48±0.40(Predicted)
• CAS DataBase Reference: Tricetin(CAS DataBase Reference)
• NIST Chemistry Reference: Tricetin(520-31-0)
• EPA Substance Registry System: Tricetin(520-31-0)

Safety Data

• Hazardous Substances Data: 520-31-0(Hazardous Substances Data)

Usage

Definition

ChEBI: Flavone hydroxylated at positions 3', 4', 5, 5' and 7.

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

Synthetic route

5,7-Dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one (53350-26-8) → tricetin (520-31-0)

Conditions	Yield
With pyridine hydrochloride at 240 - 245℃; for 0.833333h;	80%
With hydrogen bromide In water Reflux;	28%

5,7-dihydroxy-3',4',5'-trimethoxyflavone (18103-42-9) → tricetin (520-31-0)

Conditions	Yield
With hydrogen bromide In acetic acid for 23h; Heating;	38%
With hydrogen iodide; acetic anhydride

4,6-bis(methoxymethyl)-2-(3,4,5-triacetoxybenzoyloxy)acetophenone → tricetin (520-31-0)

Conditions	Yield
Stage #1: 4,6-bis(methoxymethyl)-2-(3,4,5-triacetoxybenzoyloxy)acetophenone With potassium hydroxide In pyridine at 50℃; for 0.333333h; Stage #2: With acetic acid In pyridine; water for 0.5h; Stage #3: With hydrogenchloride In methanol Reflux;	10%

1-(2,4,6-trimethoxy-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propane-1,3-dione → tricetin (520-31-0)

Conditions	Yield
With hydrogen iodide

5,7-trimethoxy-2-<3,4,5-trimethoxy-phenyl>-chromen-4-one → tricetin (520-31-0)

Conditions	Yield
With hydrogen iodide; acetic anhydride

tricine → tricetin (520-31-0)

Conditions	Yield
With hydrogen iodide; acetic anhydride

2,4,6-trihydroxyacetophenone (480-66-0) → tricetin (520-31-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium-<3,4,5-trimethoxy benzoate> / 175 °C / anschliessend Erwaermen mit wss.-aethanol. Kalilauge und Erwaermen des Reaktionsprodukts mit Essigsaeure 2: aqueous hydriodic acid; acetic acid anhydride View Scheme
Multi-step reaction with 2 steps 1: sodium-<3,4,5-trimethoxy benzoate> / 175 °C / Erwaermen des Reaktionsprodukts mit wss.-aethanol. Kalilauge 2: aqueous hydriodic acid; acetic acid anhydride View Scheme
Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 16 h / 20 °C 2: potassium carbonate / acetone / 24 h / 20 °C / Inert atmosphere 3: pyridine; sodium hydroxide / 2 h / 50 °C / Inert atmosphere 4: acetic acid; sulfuric acid / 5 h / 90 °C 5: pyridine hydrochloride / 0.83 h / 240 - 245 °C View Scheme
Multi-step reaction with 4 steps 1: potassium carbonate / acetone / 4 h / Inert atmosphere; Reflux 2: potassium hydroxide / ethanol / 24 h / 0 - 20 °C / Inert atmosphere 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 12 h / 80 °C / Sealed tube 4: hydrogen bromide / water / Reflux View Scheme

3,4,5-trimethoxybenzoic anhydride (1719-88-6) → tricetin (520-31-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium-<3,4,5-trimethoxy benzoate> / 175 °C / anschliessend Erwaermen mit wss.-aethanol. Kalilauge und Erwaermen des Reaktionsprodukts mit Essigsaeure 2: aqueous hydriodic acid; acetic acid anhydride View Scheme
Multi-step reaction with 2 steps 1: sodium-<3,4,5-trimethoxy benzoate> / 175 °C / Erwaermen des Reaktionsprodukts mit wss.-aethanol. Kalilauge 2: aqueous hydriodic acid; acetic acid anhydride View Scheme

3,4,5-trimethoxybenzoic acid methyl ester (1916-07-0) → tricetin (520-31-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium / 140 °C 2: hydriodic acid View Scheme

1-(2,4,6-trimethoxyphenyl)ethanone (832-58-6) → tricetin (520-31-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium / 140 °C 2: hydriodic acid View Scheme

3,4,5-triacetoxybenzoyl chloride (70475-59-1) + 1-(2-Hydroxy-4,6-bis(methoxymethyl)phenyl)ethanone → tricetin (520-31-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: pyridine / 20 °C 2.1: potassium hydroxide / pyridine / 0.33 h / 50 °C 2.2: 0.5 h 2.3: Reflux View Scheme

C11H14O5 → tricetin (520-31-0)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water / 0.17 h / 0 °C 1.2: 0 °C 2.1: pyridine / 20 °C 3.1: potassium hydroxide / pyridine / 0.33 h / 50 °C 3.2: 0.5 h 3.3: Reflux View Scheme

3,4,5-triacetoxy-benzoic acid methyl ester (20189-90-6) → tricetin (520-31-0)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: thionyl chloride / chloroform; N,N-dimethyl-formamide / Reflux 2.1: pyridine / 20 °C 3.1: potassium hydroxide / pyridine / 0.33 h / 50 °C 3.2: 0.5 h 3.3: Reflux View Scheme

2-hydroxy-4,6-dimethoxyacetophenone (90-24-4) → tricetin (520-31-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium carbonate / acetone / 24 h / 20 °C / Inert atmosphere 2: pyridine; sodium hydroxide / 2 h / 50 °C / Inert atmosphere 3: acetic acid; sulfuric acid / 5 h / 90 °C 4: pyridine hydrochloride / 0.83 h / 240 - 245 °C View Scheme
Multi-step reaction with 3 steps 1: potassium hydroxide / ethanol / 24 h / 0 - 20 °C / Inert atmosphere 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 12 h / 80 °C / Sealed tube 3: hydrogen bromide / water / Reflux View Scheme

2-acetyl-3,5-dimethoxyphenyl-3,4,5-trimethoxyphenyl ester (121817-16-1) → tricetin (520-31-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine; sodium hydroxide / 2 h / 50 °C / Inert atmosphere 2: acetic acid; sulfuric acid / 5 h / 90 °C 3: pyridine hydrochloride / 0.83 h / 240 - 245 °C View Scheme

(E)-1-(2′-hydroxy-4′,6′-dimethoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (53350-27-9) → tricetin (520-31-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 12 h / 80 °C / Sealed tube 2: hydrogen bromide / water / Reflux View Scheme

chlorosulfuric acid 2,2,2-trichloroethyl ester (764-09-0) + tricetin (520-31-0) → C25H15Cl15O22S5

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran at 20℃;	92%

tricetin (520-31-0) → 7-acetoxy-5-hydroxy-2-(3,4,5-triacetoxy-phenyl)-chromen-4-one

tricetin (520-31-0) + S-adenosyl-L-methionine (485-80-3, 15519-60-5, 60018-85-1, 60018-86-2, 79845-28-6) → 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1)

Conditions	Yield
With Citrus reticulata O-methyltransferase gene-pET32a recombinant In aq. buffer at 37℃; for 2h; pH=8; Kinetics; Enzymatic reaction;

Upstream product

• 18103-42-9 5,7-dihydroxy-3',4',5'-trimethoxyflavone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 1719-88-6 3,4,5-trimethoxybenzoic anhydride 
• 1916-07-0 3,4,5-trimethoxybenzoic acid methyl ester 
• 832-58-6 1-(2,4,6-trimethoxyphenyl)ethanone 
• 70475-59-1 3,4,5-triacetoxybenzoyl chloride 
• 20189-90-6 3,4,5-triacetoxy-benzoic acid methyl ester 
• 53350-26-8 5,7-Dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 121817-16-1 2-acetyl-3,5-dimethoxyphenyl-3,4,5-trimethoxyphenyl ester 
• 53350-27-9 (E)-1-(2′-hydroxy-4′,6′-dimethoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 

Downstream Products

• 520-32-1 5,7,4'trihydroxy-3',5'-dimethoxyflavone 

Relevant articles and documents

Unraveling the anti-influenza effect of flavonoids: Experimental validation of luteolin and its congeners as potent influenza endonuclease inhibitors

The biological effects of flavonoids on mammal cells are diverse, ranging from scavenging free radicals and anti-cancer activity to anti-influenza activity. Despite appreciable effort to understand the anti-influenza activity of flavonoids, there is no clear consensus about their precise mode-of-action at a cellular level. Here, we report the development and validation of a screening assay based on AlphaScreen technology and illustrate its application for determination of the inhibitory potency of a large set of polyols against PA N-terminal domain (PA-Nter) of influenza RNA-dependent RNA polymerase featuring endonuclease activity. The most potent inhibitors we identified were luteolin with an IC50 of 72 ± 2 nM and its 8-C-glucoside orientin with an IC50 of 43 ± 2 nM. Submicromolar inhibitors were also evaluated by an in vitro endonuclease activity assay using single-stranded DNA, and the results were in full agreement with data from the competitive AlphaScreen assay. Using X-ray crystallography, we analyzed structures of the PA-Nter in complex with luteolin at 2.0 ? resolution and quambalarine B at 2.5 ? resolution, which clearly revealed the binding pose of these polyols coordinated to two manganese ions in the endonuclease active site. Using two distinct assays along with the structural work, we have presumably identified and characterized the molecular mode-of-action of flavonoids in influenza-infected cells.

A new synthesis for acacetin, chrysoeriol, diosmetin, tricin and other hydroxylated flavones by modified Baker-Venkataraman transformation

Baker-Venkataraman (BV) rearrangement is the method of choice for the synthesis of flavones. The major limitation of BV is that it requires extensive protections and deprotections of hydroxyl groups which make the process lengthy and cumbersome. In the present study, a three step efficient method has been developed using simple protecting groups and easily available starting materials. New syntheses for acacetin, chrysoeriol, diosmetin, tricin and other hydroxylated flavones are described.