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 
• 64-19-7 acetic acid 
• 75-36-5 acetyl chloride 
• 61780-34-5 5-(benzyloxy)-1,2,3-trimethoxybenzene 
• 63591-70-8 2',4',5,5',6,7-hexamethoxyflavone 
• 87402-97-9 2',3',4',5,5',6,7-heptamethoxyflavone 
• 6962-57-8 3,6-dihydroxy-2,4-dimethoxyacetophenone 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 7446-70-0 aluminium trichloride 
• 17742-46-0 acetic acid 3,4,5-trimethoxy-phenyl ester 
• 98-95-3 nitrobenzene 
• 60-29-7 diethyl ether 
• 63635-39-2 2,3,4,6-tetrahydroxyacetophenone 

Downstream Products

• 198203-73-5 1,2-dihydroxy-3,4,5-trimethoxybenzene 
• 14401-58-2 2-ethyl-3,4,5-trimethoxy-phenol 
• 100126-11-2 1-(2,3,4-trimethoxy-5-bromo-6-hydroxyphenyl)ethan-1-one 
• 57197-14-5 2-Acetyl-3,4,4,5-tetramethoxycyclohexa-2,5-dienon 
• 123768-54-7 2'-hydroxy-2,4,5,4',5',6'-hexamethoxychalkone 
• 105827-27-8 2-benzyloxy-2'-hydroxy-4,4',5,5',6'-pentamethoxychalcone 
• 105827-25-6 4-benzyloxy-2'-hydroxy-2,3,4',5',6,6'-hexamethoxychalcone 
• 111786-39-1 2,4-dibenzyloxy-2'-hydroxy-3,4',5',6,6'-pentamethoxychalcone 
• 89354-98-3 2'-hydroxy-4-benzyloxy-3,5,4',5',6'-pentamethoxychalkone 
• 93092-17-2 2'-hydroxy-2,3,4',5,5',6'-hexamethoxychalcone 
• 93827-68-0 2'-Hydroxy-4',5',6',2,3,4,5-heptamethoxychalkone 
• 89426-73-3 3,4-dibenzyloxy-2'-hydroxy-4',5',6',5-tetramethoxychalcone 
• 109656-38-4 2,4-dibenzyloxy-2'-hydroxy-4',5,5',6'-tetramethoxychalcone 
• 105827-30-3 2,5-dibenzyloxy-2'-hydroxy-4,4',5',6'-tetramethoxychalcone 

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 derivative as well as preparation method and application thereof (by machine translation)

The invention discloses a baicalein derivative, structure as shown in the specification : In-flight, R1 A hydrogen, alkyl, is substituted or unsubstituted aryl ;R. 2 The hydrogen, halogen, alkyl, alkoxy, may be substituted or unsubst

Synthetic method for portulacanone compounds and their derivatives and anti-inflammatory pharmaceutical compounds containing thereof

The present inventors synthesized described portulacanone derivatives (compound 1: R^1, R^2 = H; and compound 2: R^1, R^2 = H), natural homoisoflavonoids (andplusmn;)-portulacanone A-C (compound 4: R^1 = OMe, R^2 = H; compound 8: R^1, R^2 = OMe; and compound 9: R^1 = OH, R^2 = OMe), and derivatives thereof (compound 3: R^1 = OMe, R^2 = H; compound 5: R^1 = OH, R^2 = H, and compound 7: R^1, R^2 = OMe), and thus evaluated ability to inhibit NO production in LPS-induced RAW 264.7 macrophages as an indicator of anti-inflammatory activity. All tested compounds showed no clear cytotoxicity and inhibited NO production in a concentration dependent manner in RAW 264.7 macrophages. A compound 3 (97.2% inhibition at 10 andmu;M; IC50 = 1.26 andmu;M) shows a significant inhibition effect compared to a compound 1 (91.4% inhibition at 10 andmu;M; IC50 = 1.75 andmu;M) and a compound 7 (83.0% inhibition at 10 andmu;M; IC50 = 2.91 andmu;M). Compounds of the present invention are useful for developing NO producing targeted anti-inflammatory drugs.COPYRIGHT KIPO 2019