22248-14-2

Basic information

• Product Name: 2,3,4-TRIMETHOXY-6-HYDROXYACETOPHENONE
• Synonyms: 6-HYDROXY-2,3,4-TRIMETHOXYACETOPHENONE;2,3,4-TRIMETHOXY-6-HYDROXYACETOPHENONE;6-HYDROXY-2,3,4-TRIMETHOXYACET OPHENONE 97%;2,3,4-TRIMETHOXY-6-HYDROXYACETOPHENONE 97%;1-(6-Hydroxy-2,3,4-trimethoxyphenyl)ethanone
• CAS NO: 22248-14-2
• Molecular Formula: C₁₁H₁₄O₅
• Molecular Weight: 226.23
• Product Categories: Aromatic Acetophenones & Derivatives (substituted)
• Mol File: 22248-14-2.mol
• Article Data: 31

Chemical Properties

• Melting Point: 164–165°C
• Boiling Point: 366.771°C at 760 mmHg
• Flash Point: 140.811°C
• Appearance: /
• Density: 1.182g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.52
• CAS DataBase Reference: 2,3,4-TRIMETHOXY-6-HYDROXYACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-TRIMETHOXY-6-HYDROXYACETOPHENONE(22248-14-2)
• EPA Substance Registry System: 2,3,4-TRIMETHOXY-6-HYDROXYACETOPHENONE(22248-14-2)

Safety Data

• Hazardous Substances Data: 22248-14-2(Hazardous Substances Data)

Usage

Description

2,3,4-TRIMETHOXY-6-HYDROXYACETOPHENONE is an organic compound that serves as an intermediate in the synthesis of various flavonoids and other related compounds. It is characterized by its chemical structure, which includes three methoxy groups at the 2, 3, and 4 positions, and a hydroxy group at the 6 position, attached to an acetophenone backbone.

Uses

Used in Pharmaceutical Industry:
2,3,4-TRIMETHOXY-6-HYDROXYACETOPHENONE is used as an intermediate for the synthesis of various pharmaceutical compounds, such as Eupatorin 5-Methyl Ether (E938850), Sinensetin, eupatorin, 3''-hydroxy-5,6,7,4''-tetramethoxyflavone, and rosmarinic acid. These compounds have potential applications in the development of new drugs and therapies due to their diverse biological activities.
Used in Nutraceutical Industry:
2,3,4-TRIMETHOXY-6-HYDROXYACETOPHENONE is also used in the synthesis of compounds with antioxidative properties, such as those found in Orthosiphon stamineus from Malaysia. These compounds can be utilized in the development of nutraceutical products, which aim to provide health benefits beyond basic nutrition.

Preparation

Preparation by Fries rearrangement of antiarol acetate (3,4,5-trimethoxyphenyl acetate) with aluminium chloride in nitrobenzene at r.t. (54%).

InChI:InChI=1/C11H14O5/c1-6(12)9-7(13)5-8(14-2)10(15-3)11(9)16-4/h5,13H,1-4H3

Upstream product

• 642-71-7 3,4,5-trimethoxyphenol 
• 108-24-7 acetic anhydride 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 17742-46-0 acetic acid 3,4,5-trimethoxy-phenyl ester 
• 64-19-7 acetic acid 
• 78-79-5 isoprene 
• 100-52-7 benzaldehyde 
• 7702-17-2 4-(acetyloxy)-3,5-dimethoxyphenyl acetate 
• 96410-44-5 5-hydroxy-2',4',5',6,7-pentamethoxyflavone 
• 63635-39-2 2,3,4,6-tetrahydroxyacetophenone 
• 77-78-1 dimethyl sulfate 
• 7446-70-0 aluminium trichloride 
• 60-29-7 diethyl ether 
• 61780-34-5 5-(benzyloxy)-1,2,3-trimethoxybenzene 

Downstream Products

• 4324-55-4 3,4',5,6,7-pentahydroxyflavone 
• 1168-42-9 5,6,7,4'-tetramethoxyflavone 
• 5867-71-0 3-hydroxy-5,6,7,4'-tetramethoxymethoxyflavone 
• 870480-20-9 (E)-3-(dimethylamino)-6'-hydroxy-2',3',4'-trimethoxyacrylophenone 
• 59567-92-9 (E)-1-(6-hydroxy-2,3,4-trimethoxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one 
• 6938-18-7 5,7-dihydroxy-2-(3,4,5-trimethoxyphenyl)-4Hchromen-4-one 

Relevant articles and documents

TWO POLYMETHOXYFLAVONES FROM AGERATUM HOUSTONIANUM

Besides agecorynin C, eupalestin and lucidin dimethyl ether, two new highly oxygenated flavones were isolated from Ageratum houstonianum.Their structures were established by spectroscopic and degradative evidence as 5,6,7,8,2',3',4',5'-octamethoxyflavone and 5,6,7,2',3',4',5'-heptamethoxyflavone. - Key Word Index: Ageratum houstonianum; Asteraceae; Eupatorieae; new octasubstituted and heptasubstituted flavones.

Total synthesis of baicalein

In this paper, a simple and novel synthesis of baicalein is described. This transformation features the novel synthesis of helilandin B and a different way to demethylate. The overall yield of 59% is acceptable.

Synthesis and anti-proliferative activities of 5,6,7-trimethoxyflavones and their derivatives

A series of 5,6,7-trimethoxyflavones 1a-1g and their derivatives 2a-2g, 3a-3d, 4 and 5, including the natural products 5,6,7-trimethoxy-4’-hydroxyflavone (1a), 5,6,7,3’,4’ -pentamethoxyflavone (sinensetin, 1 b), 5,6,7-trimethoxy-3’,4’-methyl enedioxy flavone (1c), 5,6,7,3’-tetramethoxy-4,5’-methylenedioxyflavone (1e), 5,6,7, 3’,4’,5’-hextamethoxyflavone (1 g), 5-hydroxy-3,4,2’,3’,4’-pentamethoxy chal-cone (2 b), 5,4’-dihydroxy-6,7-dimethoxy flavone (cirsimaritin, 3a) and 5-hydroxy-6,7,3’, 4’-tetramethoxyflavone (5-demethylsinensetin, 3 b), 3,5,6,7,3’,4’-hexamethoxyflavone (3-methoxysinensetin, 4) and 5’-hydroxy-3,6,7,3’,4’-pentamethoxyflavone (5) were synthesized. Their anti-proliferative activity in?vitro was evaluated against a panel of four human cancer cell lines (Aspc-1, HCT-116, HepG-2 and SUN-5) by the CTG assay. The results showed that most of the synthetic compounds exhibited moderate to high anti-proliferative activities. In particular, compound 3c possess IC50 (5.30 μM) values below 10 μM against Aspc-1 cells and are worthy of further investigation.

Baicalein or derivative thereof, preparation method and application of baicalein or derivative of baicalein

The invention discloses baicalein or a derivative thereof. The structure is shown in the specification, wherein R1 is hydrogen, alkyl, substituted or unsubstituted aryl; R2 is hydrogen, halogen, alkyl, alkoxy, substituted or unsubstituted amino, and subst

Natural products hybrids: 3,5,4′-Trimethoxystilbene-5,6,7-trimethoxyflavone chimeric analogs as potential cytotoxic agents against diverse human cancer cells

Cancer still represents a major global health problem. All currently available anticancer agents have disadvantages like resistance or side effects. Therefore, introduction of novel anticancer agents is needed. Intrigued by the high success rate for natural products-based drug discovery, we designed and synthesized antiproliferative chemical entities as hybrids of two natural products; 3,5,4′-trimethoxystilbene and 5,6,7-trimethoxyflavone. To probe the spectrum of the synthesized compounds, in vitro evaluation was conducted against nine panels representing major cancer diseases. The results revealed the hybrid analogs 4f, 4h, 4k and 4q as promising broad-spectrum anticancer lead compounds eliciting high growth inhibition of several cell lines representing multiple cancers diseases. Evaluation of the promising lead compounds against normal human cell lines suggested a selective cytotoxic effect on cancer cells. Mechanistic investigation of the cytotoxic activity of compound 4f in human cervical cancer HeLa cells showed that it triggers cell death through induction of apoptosis. As a whole, this study presents the natural products hybrid analogs 4f, 4h, 4k and 4q as potential lead compounds for further development of novel anticancer therapeutics.