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

Uses

6-Hydroxy-2,3,4-trimethoxyacetophenone is an intermediate in synthesizing Eupatorin 5-Methyl Ether (E938850), Sinensetin, eupatorin, 3''-hydroxy-5,6,7,4''-tetramethoxyflavone and rosmarinic acid contents and antioxidative effect of Orthosiphon stamineus from Malaysia.

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 
• 17742-46-0 acetic acid 3,4,5-trimethoxy-phenyl ester 
• 108-24-7 acetic anhydride 
• 100-52-7 benzaldehyde 
• 78-79-5 isoprene 
• 86-81-7 3,4,5-trimethoxy-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

• 340816-26-4 2-hydroxy-4,5,6-trimethoxy-3-C-prenylacetophenone 
• 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 
• 96071-56-6 2'-Hydroxy-4.4'.5'.6'-tetramethoxy-3-benzyloxy-chalkon 
• 105827-32-5 2',4'-dibenzyloxy-3-hydroxy-5,5',6,7-tetramethoxyflavone 
• 95412-53-6 3'-benzyloxy-2',4',5,6,6',7-hexamethoxyflavone 
• 95412-52-5 2'-isopropyloxy-3',4',5,6,6',7-hexamethoxyflavone 
• 95412-51-4 6'-isopropyloxy-2',3',4',5,6,7-hexamethoxyflavone 
• 105827-24-5 3'-hydroxy-2',4',5,6,6',7-hexamethoxyflavone 
• 95412-50-3 3',5-dihydroxy-2',4',6,6',7-pentamethoxyflavone 
• 95412-49-0 2',5-dihydroxy-3',4',6,6',7-pentamethoxyflavone 
• 93124-90-4 4'-hydroxy-3',5,5',6,7-pentamethoxyflavone 

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

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