1-(6-Hydroxy-2,3,4-trimethoxyphenyl)ethanone

Base Information

• Chemical Name: 1-(6-Hydroxy-2,3,4-trimethoxyphenyl)ethanone
• CAS No.: 22248-14-2
• Molecular Formula: C11H14O5
• Molecular Weight: 226.229
• Hs Code.: 2914509090
• European Community (EC) Number: 847-981-9
• Nikkaji Number: J455.934G
• Mol file: 22248-14-2.mol

Synonyms:1-(6-hydroxy-2,3,4-trimethoxyphenyl)ethanone;22248-14-2;6-Hydroxy-2,3,4-trimethoxyacetophenone;1-(6-Hydroxy-2,3,4-trimethoxyphenyl)ethan-1-one;SCHEMBL735664;MLYYVUJNBLMMPE-UHFFFAOYSA-N;CS-0232302;FT-0638203;2',3',4'-Trimethoxy-6'-hydroxyacetophenone;6'-hydroxy-2',3',4'-trimethoxy-acetophenone;1-(6-hydroxy-2,3,4,-trimethoxyphenyl)ethanone;EN300-1268193

Chemical Property of 1-(6-Hydroxy-2,3,4-trimethoxyphenyl)ethanone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 164–165°C
• Boiling Point: 366.771oC at 760 mmHg
• Flash Point: 140.811oC
• PSA: 64.99000
• Density: 1.182g/cm3
• LogP: 1.62060
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 226.08412354
• Heavy Atom Count: 16
• Complexity: 243

Purity/Quality:

98%min ^*data from raw suppliers

6-Hydroxy-2,3,4-trimethoxyacetophenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=C(C(=C(C=C1O)OC)OC)OC
• 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.

Technology Process of 1-(6-Hydroxy-2,3,4-trimethoxyphenyl)ethanone

There total 22 articles about 1-(6-Hydroxy-2,3,4-trimethoxyphenyl)ethanone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

acetic acid 3,4,5-trimethoxy-phenyl ester (17742-46-0) → 6-hydroxy-2,3,4-trimethoxyacetophenone (22248-14-2)

Guidance literature:

With boron trifluoride diethyl etherate; acetic acid; at 70 ℃; for 2h;

DOI:10.1007/s12039-016-1042-z

Reference yield: 95.0%

3,4,5-trimethoxyphenol (642-71-7) + acetic anhydride (108-24-7) → 6-hydroxy-2,3,4-trimethoxyacetophenone (22248-14-2)

Guidance literature:

3,4,5-trimethoxyphenol; acetic anhydride; With boron trifluoride diethyl etherate; at 0 - 60 ℃; for 3h;

With water; triethylamine; at 20 ℃; for 1h;

Reference yield: 94.0%

acetic acid 3,4,5-trimethoxy-phenyl ester (17742-46-0) + acetic acid (64-19-7,77671-22-8) → 6-hydroxy-2,3,4-trimethoxyacetophenone (22248-14-2)

Guidance literature:

With boron trifluoride diethyl etherate; at 70 ℃; for 2h; Inert atmosphere;

upstream raw materials:

3,4,5-trimethoxyphenol

acetic acid

acetyl chloride

5-(benzyloxy)-1,2,3-trimethoxybenzene

Downstream raw materials:

2-Acetyl-3,4,4,5-tetramethoxycyclohexa-2,5-dienon

(E)-3-(2,5-Bis-benzyloxy-phenyl)-1-(6-hydroxy-2,3,4-trimethoxy-phenyl)-propenone

2-hydroxy-4,5,6-trimethoxy-3-C-prenylacetophenone

3,4',5,6,7-pentahydroxyflavone

Refernces

• 1、 Huang, Wen-Hsin,Chien, Pei-Yu,Yang, Ching-Huey,Lee, An-Rong. "Novel synthesis of flavonoids of Scutellaria baicalensis Georgi.". . p. 339 - 340. Retrieved 2003.
• 2、 Panichpol,Waterman. "". . p. 1363,1364-1366. Retrieved 1978.
• 3、 -. "Baicalein or derivative thereof, preparation method and application of baicalein or derivative of baicalein". Paragraph 0088; 0163; 0165. . Retrieved 2020/04/17.
• 4、 -. "chromane derivatives, and pharmaceutical composition for preventing or treating neovascular eye disease or cancer containing the same as an active ingredient". Paragraph 0272-0277. . Retrieved 2020/12/01.