16545-23-6

Basic information

• Product Name: 5,4''-DIHYDROXY-6,7,8-TRIMETHOXYFLAVONE
• Synonyms: 4',5-Dihydroxy-6,7,8-trimethoxyflavone;5-Hydroxy-2-(4-hydroxyphenyl)-6,7,8-trimethoxy-4H-1-benzopyran-4-one;5-hydroxy-2-(4-hydroxyphenyl)-6,7,8-trimethoxy-4H-chromen-4-one;4H-1-Benzopyran-4-one,5-hydroxy-2-(4-hydroxyphenyl)-6,7,8-trimethoxy-
• CAS NO: 16545-23-6
• Molecular Formula: C₁₈H₁₆O₇
• Molecular Weight: 344.32
• Product Categories: Penta-substituted Flavones
• Mol File: 16545-23-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 225 °C
• Boiling Point: 609.9°Cat760mmHg
• Flash Point: 225°C
• Appearance: /
• Density: 1.387g/cm³
• PKA: 6.85±0.40(Predicted)
• CAS DataBase Reference: 5,4''-DIHYDROXY-6,7,8-TRIMETHOXYFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,4''-DIHYDROXY-6,7,8-TRIMETHOXYFLAVONE(16545-23-6)
• EPA Substance Registry System: 5,4''-DIHYDROXY-6,7,8-TRIMETHOXYFLAVONE(16545-23-6)

Safety Data

• Hazardous Substances Data: 16545-23-6(Hazardous Substances Data)

Usage

Description

5,4''-DIHYDROXY-6,7,8-TRIMETHOXYFLAVONE is a trimethoxyflavone compound characterized by the presence of methoxy groups at positions 6, 7, and 8, and hydroxy groups at positions 5 and 4'. It is a flavonoid, a group of naturally occurring compounds found in plants, known for their diverse biological activities and potential health benefits.

Uses

Used in Pharmaceutical Industry:
5,4''-DIHYDROXY-6,7,8-TRIMETHOXYFLAVONE is used as a bioactive compound for its potential therapeutic applications. It has been found to possess various pharmacological properties, such as antioxidant, anti-inflammatory, and anticancer activities, making it a promising candidate for the development of new drugs and treatments.
Used in Anticancer Applications:
In the field of oncology, 5,4''-DIHYDROXY-6,7,8-TRIMETHOXYFLAVONE is used as an anticancer agent. It has been shown to inhibit the growth of certain cancer cell lines, such as human prostate cancer LNCaP cells, by epigenetically restoring p21 gene expression and inhibiting cancer stem-like cell proliferation. This suggests its potential use in the development of targeted cancer therapies.
Used in Nutraceutical Industry:
5,4''-DIHYDROXY-6,7,8-TRIMETHOXYFLAVONE can also be used in the nutraceutical industry as a dietary supplement or functional ingredient due to its antioxidant and anti-inflammatory properties. These properties may contribute to the overall health and well-being of consumers, supporting immune function and reducing the risk of chronic diseases.
Used in Cosmetic Industry:
In the cosmetic industry, 5,4''-DIHYDROXY-6,7,8-TRIMETHOXYFLAVONE may be utilized for its potential skin health benefits. Its antioxidant and anti-inflammatory properties could be harnessed in skincare products to protect the skin from environmental stressors, reduce inflammation, and promote a healthy, youthful appearance.
Used in Agricultural Industry:
5,4''-DIHYDROXY-6,7,8-TRIMETHOXYFLAVONE may also find applications in the agricultural industry, particularly in the development of natural pesticides or growth promoters. Its bioactive properties could be leveraged to enhance crop yield, improve resistance to diseases, or act as a natural alternative to synthetic chemicals in agriculture.

Synthetic route

4'-benzyloxy-5,6,7,8-tetramethoxyflavone (40110-96-1) → xanthomicrol (16545-23-6)

Conditions	Yield
Stage #1: 4'-benzyloxy-5,6,7,8-tetramethoxyflavone With boron trichloride In dichloromethane; toluene at -78 - 20℃; for 12h; Inert atmosphere; Stage #2: With water; sodium hydroxide In dichloromethane; toluene at 20℃; for 0.5h;	87%
Multi-step reaction with 2 steps 1: 120 mg / H2 / Pd-C / ethyl acetate 2: AlCl3 / nitrobenzene / Ambient temperature View Scheme

4'-hydroxy-5,6,7,8-tetramethoxy flavone (36950-98-8) → xanthomicrol (16545-23-6)

Conditions	Yield
With aluminium trichloride In nitrobenzene Ambient temperature;

p-benzyloxybenzaldehyde (4397-53-9) → xanthomicrol (16545-23-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.0 g / KOH / aq. ethanol / Ambient temperature 2: 450 mg / 85percent H3PO4 / ethanol / 50 h / Heating 3: 350 mg / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 10 h / Heating 4: 120 mg / H2 / Pd-C / ethyl acetate 5: AlCl3 / nitrobenzene / Ambient temperature View Scheme

4-benzyloxy-2'-hydroxy-3',4',5',6'-tetramethoxychalcone (40110-95-0) → xanthomicrol (16545-23-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 450 mg / 85percent H3PO4 / ethanol / 50 h / Heating 2: 350 mg / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 10 h / Heating 3: 120 mg / H2 / Pd-C / ethyl acetate 4: AlCl3 / nitrobenzene / Ambient temperature View Scheme

2-hydroxy-3,4,5,6-tetramethoxyacetophenone (3162-28-5) → xanthomicrol (16545-23-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.0 g / KOH / aq. ethanol / Ambient temperature 2: 450 mg / 85percent H3PO4 / ethanol / 50 h / Heating 3: 350 mg / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 10 h / Heating 4: 120 mg / H2 / Pd-C / ethyl acetate 5: AlCl3 / nitrobenzene / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1.1: dmap; triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice; Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 1 h / Reflux; Inert atmosphere 3.1: toluene-4-sulfonic acid / benzene / 7 h / Reflux; Inert atmosphere 4.1: boron trichloride / dichloromethane; toluene / 12 h / -78 - 20 °C / Inert atmosphere 4.2: 0.5 h / 20 °C View Scheme

4'-benzyloxy-5,6,7,8-tetramethoxyflavanone (73898-14-3) → xanthomicrol (16545-23-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 350 mg / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 10 h / Heating 2: 120 mg / H2 / Pd-C / ethyl acetate 3: AlCl3 / nitrobenzene / Ambient temperature View Scheme

2-(4-benzyloxybenzoyloxy)-3,4,5,6-tetramethoxyacetophenone (1350827-37-0) → xanthomicrol (16545-23-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium tert-butylate / tetrahydrofuran / 1 h / Reflux; Inert atmosphere 2.1: toluene-4-sulfonic acid / benzene / 7 h / Reflux; Inert atmosphere 3.1: boron trichloride / dichloromethane; toluene / 12 h / -78 - 20 °C / Inert atmosphere 3.2: 0.5 h / 20 °C View Scheme

1-(4-benzyloxyphenyl)-3-(2-hydroxy-3,4,5,6-tetramethoxyphenyl)propane-1,3-dione (85374-52-3) → xanthomicrol (16545-23-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: toluene-4-sulfonic acid / benzene / 7 h / Reflux; Inert atmosphere 2.1: boron trichloride / dichloromethane; toluene / 12 h / -78 - 20 °C / Inert atmosphere 2.2: 0.5 h / 20 °C View Scheme

4-(benzyloxy)benzoic acid chloride (1486-50-6) → xanthomicrol (16545-23-6)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: dmap; triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice; Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 1 h / Reflux; Inert atmosphere 3.1: toluene-4-sulfonic acid / benzene / 7 h / Reflux; Inert atmosphere 4.1: boron trichloride / dichloromethane; toluene / 12 h / -78 - 20 °C / Inert atmosphere 4.2: 0.5 h / 20 °C View Scheme

xanthomicrol (16545-23-6) + dimethyl sulfate (77-78-1) → gardenin B (2798-20-1)

Conditions	Yield
With potassium carbonate In dichloromethane; acetone for 4h; Reflux;	44.6%

xanthomicrol (16545-23-6) + dimethyl sulfate (77-78-1) → gardenin B (2798-20-1) + tangeritin (481-53-8)

Conditions	Yield
With potassium carbonate In dichloromethane; acetone for 4h; Reflux;	A 31.8% B 8%

xanthomicrol (16545-23-6) → 5,6,4'-trihydroxyl-7,8-dimethoxyflavone (76844-66-1)

Conditions	Yield
With hydrogenchloride In methanol; water at 100℃; for 48h;	5%

xanthomicrol (16545-23-6) → 8-demethylthymusin (98755-26-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 5 percent / 4N HCl / methanol; H2O / 48 h / 100 °C 2: 30 percent / 4N HCl / methanol; H2O / 4 h / 100 °C View Scheme

xanthomicrol (16545-23-6) → 6,7-dimethoxy-5,8,4′-trihydroxyflavone (98755-25-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 5 percent / 4N HCl / methanol; H2O / 48 h / 100 °C 2: 10 percent / 4N HCl / methanol; H2O / 4 h / 100 °C View Scheme

Upstream product

• 36950-98-8 4'-hydroxy-5,6,7,8-tetramethoxy flavone 
• 73898-14-3 4'-benzyloxy-5,6,7,8-tetramethoxyflavanone 
• 1486-50-6 4-(benzyloxy)benzoic acid chloride 
• 85374-52-3 1-(4-benzyloxyphenyl)-3-(2-hydroxy-3,4,5,6-tetramethoxyphenyl)propane-1,3-dione 
• 1350827-37-0 2-(4-benzyloxybenzoyloxy)-3,4,5,6-tetramethoxyacetophenone 
• 3162-28-5 2-hydroxy-3,4,5,6-tetramethoxyacetophenone 
• 40110-95-0 4-benzyloxy-2'-hydroxy-3',4',5',6'-tetramethoxychalcone 
• 40110-96-1 4'-benzyloxy-5,6,7,8-tetramethoxyflavone 
• 4397-53-9 p-benzyloxybenzaldehyde 

Downstream Products

• 2798-20-1 gardenin B 
• 481-53-8 tangeritin 
• 98755-25-0 6,7-dimethoxy-5,8,4′-trihydroxyflavone 
• 98755-26-1 8-demethylthymusin 
• 76844-66-1 5,6,4′-trihydroxy-7,8-dimethoxy flavone 

Relevant articles and documents

B-Ring-modified and/or 5-demethylated nobiletin congeners: Inhibitory activity against pro-MMP-9 production

Three metabolites and 12 analogues of nobiletin (1) were synthesized. Whereas nobiletin derivatives 2-4 inhibited pro-MMP-9 production similarly in both PMA- and TNF-α-stimulated human lens epithelial cells, the 2′-hydroxylated analogue 5a exerted marked inhibitory effects (IC 50: 0.4 μM) on PMA-treated cells, which were 170-fold more potent than those on TNF-α-treated cells. This activity may be closely related to PKC-mediated transcriptional regulation of pro-MMP-9.