3660-86-4

Basic information

• Product Name: 1,3,5,6-Tetramethoxy-9H-xanthen-9-one
• Synonyms: 1,3,5,6-Tetramethoxy-9H-xanthen-9-one;1,3,5,6-Tetramethoxyxanthone
• CAS NO: 3660-86-4
• Molecular Formula: C17H16O6
• Molecular Weight: 0
• Mol File: 3660-86-4.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3,5,6-Tetramethoxy-9H-xanthen-9-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5,6-Tetramethoxy-9H-xanthen-9-one(3660-86-4)
• EPA Substance Registry System: 1,3,5,6-Tetramethoxy-9H-xanthen-9-one(3660-86-4)

Safety Data

• Hazardous Substances Data: 3660-86-4(Hazardous Substances Data)

Usage

Chemical class

Xanthene class of organic compounds

Type of compound

Heterocyclic compound

Backbone structure

Xanthene backbone

Substituents

Four methoxy groups

Position of methoxy groups

1, 3, 5, and 6 positions

Usage

Organic synthesis and as a building block for other chemical compounds

Potential applications

Biological activities, including anti-tumor properties

Significance

Valuable tool in organic chemistry and medicinal chemistry due to its unique structure and properties

Molecular weight

Approximately 328.31 g/mol

Appearance

Yellow crystalline solid

Solubility

Soluble in organic solvents like ethanol, methanol, and acetone

Melting point

Around 195-198°C (382-388°F)

Stability

Stable under normal conditions, but sensitive to light and heat

Reactivity

Can undergo various chemical reactions, such as oxidation, reduction, and substitution reactions

Synthesis methods

Can be synthesized through various methods, including condensation reactions and electrophilic aromatic substitution reactions

Safety precautions

Handle with care, as it may be harmful if inhaled, ingested, or comes into contact with the skin

Storage

Store in a cool, dry, and well-ventilated area, away from light and heat sources, and in a sealed container to prevent degradation or contamination.

Upstream product

• 42833-67-0 2,4,6-trimethoxy-2'-hydroxy-3',4'-dimethoxybenzophenone 
• 7169-07-5 3,4,5-(trimethoxy)benzoyl chloride 
• 4090-81-7 1,3,5,6-tetrahydroxyxanthone tetraacetate 
• 859779-56-9 3-(1-carboxy-1-methyl-ethoxy)-1,5,6-trimethoxy-9-oxo-xanthene-2-carboxylic acid 
• 573-11-5 2,3,4-Trimethoxy-benzoic acid 
• 77-78-1 dimethyl sulfate 
• 94936-03-5 1,3-dimethoxy-5,6-dihydroxyxanthone 
• 621-23-8 1,2,3-trimethoxybenzene 
• 56124-67-5 1,3-dihydroxy-5,6-dimethoxy-9H-xanthen-9-one 
• 5084-31-1 1,3,5,6-tetrahydroxy-xanthen-9-one 

Downstream Products

• 1489235-90-6 1,3,5,6-tetramethoxy-4-phenyl-9H-xanthen-9-one 
• 1489235-91-7 4-(3,5-bis(trifluoromethyl)phenyl)-1,3,5,6-tetramethoxy-9H-xanthen-9-one 
• 1489235-92-8 4-(1,3,5,6-tetramethoxy-9-oxo-9H-xanthen-4-yl)benzaldehyde 
• 1489235-93-9 4-(3,5-difluorophenyl)-1,3,5,6-tetramethoxy-9H-xanthen-9-one 
• 1489235-94-0 1,3,5,6-Tetramethoxy-4-(4-(trifluoromethoxy)phenyl)-9H-xanthen-9-one 
• 1489235-95-1 4-(4-fluorophenyl)-1,3,5,6-tetramethoxy-9H-xanthen-9-one 
• 1489235-96-2 4-(4-ethylphenyl)-1,3,5,6-tetramethoxy-9H-xanthen-9-one 
• 1489235-97-3 1,3,5,6-tetramethoxy-4-p-tolyl-9H-xanthen-9-one 
• 1489235-98-4 4-(4-isopropylphenyl)-1,3,5,6-tetramethoxy-9H-xanthen-9-one 
• 1489236-00-1 4-(4-tert-butylphenyl)-1,3,5,6-tetramethoxy-9H-xanthen-9-one 
• 1489236-01-2 4-(4-acetylphenyl)-1,3,5,6-tetramethoxy-9H-xanthen-9-one 
• 1489236-02-3 methyl 4-(1,3,5,6-tetramethoxy-9-oxo-9H-xanthen-4-yl)benzoate 
• 1489236-03-4 1,3,5,6-tetramethoxy-4-(4-(methylsulfonyl)phenyl)-9H-xanthen-9-one 
• 1489236-04-5 4-(1,3,5,6-tetramethoxy-9-oxo-9H-xanthen-4-yl)benzonitrile 

Relevant articles and documents

Chemical constituents of gentianaceae. IV. New xanthones of Canscora decussata.

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FERRXANTHONE, A 1,3,5,6-TETRAOXYGENATED XANTHONE FROM MESUA FERREA

A new xanthone was isolated from the heartwood of Mesua ferrea and its structure determined by UV, IR, NMR and mass spectrometry as 1,3-dimethoxy-5,6-dihydroxyxanthone.Key Word Index -- Mesua ferrea; Guttiferae; heartwood; 1,3-dimethoxy-5,6-dihydroxanthone; ferrxanthone.

Synthesis and biological evaluation of phenyl substituted polyoxygenated xanthone derivatives as anti-hepatoma agents

A series of novel derivatives of phenyl substituted tetramethoxy xanthone were synthesized and evaluated for their in vitro cytotoxicity against human hepatocellular carcinoma (HCC) and non-tumor hepatic cells. Among these derivatives, compound 6 was more potent than positive control 5-fluorouracil (5-Fu) on QGY-7703 and SMMC-7721 cells with IC50 values of 6.27 μM, 7.50 μM and 15.56 μM, 14.55 μM, respectively. Furthermore, compounds 6, 14, 16, and 29 exhibited much better selectivity toward the normal hepatic cell line QSG-7701 than 5-Fu. Additionally, compound 6 significantly induced cell apoptosis in QGY-7703 cells. Our findings suggested that these phenylxanthone derivatives may hold promise as chemotherapeutic agents for the treatment of human HCC.

γ-Pyrone compounds. II: Synthesis and antiplatelet effects of tetraoxygenated xanthones

Norathyriol and its analogues, 1,3,5,6-, 3,4,5,6-, 3,4,6,7- and 2,3,6,7- tetrahydroxyxanthone, were synthesized from benzophenone precursors by Friedel-Crafts acylation and subsequent base-catalyzed cyclization to eliminate methanol. Both 3,4,6,7- and 2,3,6,7-tetrahydroxyxanthone tetraacetate showed potent anti-platelet aggregation effects on arachidonic acid-induced platelet aggregation. 3,4,6,7-Tetrahydroxyxanthone tetraacetate and 1,3,5,6-tetrahydroxyxanthone showed potent and significant anti-platelet aggregation effects on collagen-induced platelet aggregation.