2',6'-Dihydroxy-4'-methoxyacetophenone

Base Information

• Chemical Name: 2',6'-Dihydroxy-4'-methoxyacetophenone
• CAS No.: 7507-89-3
• Molecular Formula: C9H10O4
• Molecular Weight: 182.176
• NSC Number: 401443
• UNII: 82H3LB8M6Q
• DSSTox Substance ID: DTXSID80226044
• Nikkaji Number: J122.209K
• Wikidata: Q83105299
• Metabolomics Workbench ID: 43957
• ChEMBL ID: CHEMBL490514
• Mol file: 7507-89-3.mol

Synonyms:7507-89-3;2',6'-Dihydroxy-4'-methoxyacetophenone;1-(2,6-DIHYDROXY-4-METHOXYPHENYL)ETHANONE;4-O-Methylphloracetophenone;2,6-Dihydroxy-4-methoxyacetophenone;Ethanone, 1-(2,6-dihydroxy-4-methoxyphenyl)-;Acetophenone, 2',6'-dihydroxy-4'-methoxy-;2',6'-Dihydroxy-4'methoxyacetophenone;4-O-Methylphloroacetophenone;82H3LB8M6Q;CHEMBL490514;Acetophenone, 2',6'-dihydroxy-4'-methoxy- (8CI);MFCD00017518;NSC401443;NSC 401443;NSC-401443;1-(2,6-dihydroxy-4-methoxyphenyl)ethan-1-one;Desaspidinol-A;UNII-82H3LB8M6Q;SCHEMBL2811810;DTXSID80226044;HY-N9695;BDBM50071808;AKOS006230320;Acetophenone,6'-dihydroxy-4'-methoxy-;CCG-214359;Ethanone,6-dihydroxy-4-methoxyphenyl)-;NCI60_003771;SY288282;1-(2,6-dihydroxy-4-methoxy-phenyl)ethanone;2/',6/'-Dihydroxy-4/'-methoxyacetophenone;CS-0203540;Ethanone, 1-(2,6-hydroxy-4-methoxyphenyl);FT-0636518;A838319;SR-05000002418;SR-05000002418-1;Ethanone, 1-(2,6-dihydroxy-4-methoxyphenyl)- (9CI);2 inverted exclamation mark ,6 inverted exclamation mark -Dihydroxy-4 inverted exclamation mark -methoxyacetophenone

Chemical Property of 2',6'-Dihydroxy-4'-methoxyacetophenone

Chemical Property:

• Melting Point: 144 °C
• Boiling Point: 356.7 °C at 760 mmHg
• PKA: 9.27±0.15(Predicted)
• Flash Point: 146.3 °C
• PSA: 66.76000
• Density: 1.284 g/cm³
• LogP: 1.30900
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 182.05790880
• Heavy Atom Count: 13
• Complexity: 180

Purity/Quality:

99%, ^*data from raw suppliers

2',6'-Dihydroxy-4'-methoxyacetophenone 98% ^*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)O

Technology Process of 2',6'-Dihydroxy-4'-methoxyacetophenone

There total 29 articles about 2',6'-Dihydroxy-4'-methoxyacetophenone 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: 76.0%

5-methoxyresorcinol (2174-64-3) + acetyl chloride (75-36-5) → 2,6-dihydroxy-4-methoxy-acetophenone (7507-89-3)

Guidance literature:

5-methoxyresorcinol; With aluminum (III) chloride; In dichloromethane; at 0 ℃; for 0.25h; Inert atmosphere;

acetyl chloride; In dichloromethane; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1039/d0ob01985b

Reference yield: 74.0%

2-hydroxy-4,6-dimethoxyacetophenone (90-24-4) → 2,6-dihydroxy-4-methoxy-acetophenone (7507-89-3)

Guidance literature:

With lithium diphenylphosphide; In tetrahydrofuran; hexane; at 50 ℃; for 1h;

DOI:10.1002/1099-0690(200203)2002:6<1107::AID-EJOC1107>3.0.CO;2-4

Reference yield: 61.0%

bulbine-knipholone → Chrysophanol (481-74-3) + 2,6-dihydroxy-4-methoxy-acetophenone (7507-89-3)

Guidance literature:

With sodium dithionite; In sodium hydroxide; at 70 ℃; for 1h;

DOI:10.1002/1099-0690(200203)2002:6<1107::AID-EJOC1107>3.0.CO;2-4

upstream raw materials:

diazomethane

2,4,6-trihydroxyacetophenone

3-acetyl-2,4-dihydroxy-6-methoxy-benzoic acid methyl ester

2-acetyl-5-methoxy-4-trichloroacetyl-resorcinol

Downstream raw materials:

2',6'-dihydroxy-4'-methoxyacetophenone 2'-O-(2,3,4,6-O-tetraacetyl)-β-D-glucopyranoside

10-acetyl-3,4,6,7-tetrahydro-5-methoxy-2,2,8,8-tetramethyl-2H,8H-benzo<1,2-b:5,4-b'>dipyran

8-Acetyl-7-hydroxy-5-methoxy-3,4-dihydro-2,2-dimethyl-2H-<1>benzopyran

1-{2-[3-(2-Acetyl-3-hydroxy-5-methoxy-phenoxy)-2-hydroxy-propoxy]-6-hydroxy-4-methoxy-phenyl}-ethanone

Refernces

• 1、 Nagarajan,Parmar. "". . p. 614. Retrieved 1977.
• 2、 Chen, Huiyu,Lu, Xiuxiang,Tan, Haibo,Wang, Sasa,Zhang, Wenge,Zheng, Anquan,Zhou, Tingting. "Total syntheses of hyperaspidinols A and B enabled by a bioinspired diastereoselective cascade sequence". . . Retrieved 2021/09/03.
• 3、 Hofmann, Julian,Fayez, Shaimaa,Scheiner, Matthias,Hoffmann, Matthias,Oerter, Sabrina,Appelt-Menzel, Antje,Maher, Pamela,Maurice, Tangui,Bringmann, Gerhard,Decker, Michael. "Sterubin: Enantioresolution and Configurational Stability, Enantiomeric Purity in Nature, and Neuroprotective Activity in Vitro and in Vivo". . p. 7299 - 7308. Retrieved 2020/05/18.