Emodin 6,8-dimethyl ether

Base Information

• Chemical Name: Emodin 6,8-dimethyl ether
• CAS No.: 5018-84-8
• Molecular Formula: C17H14O5
• Molecular Weight: 298.295
• NSC Number: 624615
• UNII: 1DI503336G
• DSSTox Substance ID: DTXSID50326969
• Nikkaji Number: J269.596K
• Wikidata: Q27252287
• ChEMBL ID: CHEMBL451766
• Mol file: 5018-84-8.mol

Synonyms:Emodin 6,8-dimethyl ether;5018-84-8;Questin 6-methyl ether;NSC624615;1-hydroxy-6,8-dimethoxy-3-methylanthracene-9,10-dione;NSC-624615;9,10-Anthracenedione, 1-hydroxy-6,8-dimethoxy-3-methyl-;UNII-1DI503336G;1-Hydroxy-3-methyl-6,8-dimethoxyanthraquinone;1-Hydroxy-6,8-dimethoxy-3-methylanthraquinone;8-Hydroxy-1,3-dimethoxy-6-methylanthraquinone;Anthraquinone, 1-hydroxy-6,8-dimethoxy-3-methyl-;1DI503336G;Emodin,3-dimethyl ether;Emodin, 1,3-dimethyl ether;1-Hydroxy-6,8-dimethoxy-3-methylanthra-9,10-quinone;CHEMBL451766;SCHEMBL16227337;DTXSID50326969;5,7-dimethoxy-4-hydroxy-2-methyl-anthraquinone;1,3-Dimethoxy-6-methyl-8-hydroxy-9,10-anthraquinone;Q27252287;1-hydroxy-6,8-dimethoxy-3-methyl-anthracene-9,10-dione

Chemical Property of Emodin 6,8-dimethyl ether

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 298.08412354
• Heavy Atom Count: 22
• Complexity: 462

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=C(C=C3OC)OC

Technology Process of Emodin 6,8-dimethyl ether

There total 2 articles about Emodin 6,8-dimethyl ether 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: 10.0%

3-chloro-5-hydroxy-7-methoxy-1,4-naphthoquinone (65120-69-6) + (E)-((1-methoxy-3-methylbuta-1,3-dien-1-yl)oxy)trimethylsilane (76927-59-8) → physcion (521-61-9) + emodin-6,8-di-O-methyl ether (5018-84-8) + methyl 3-methyl-4-<3-chloro-5-hydroxy-7-methoxynaphthoquinonyl-2>-2-butenoate (95393-78-5)

Guidance literature:

In tetrahydrofuran; Ambient temperature;

DOI:10.1016/S0040-4020(01)91496-6

Reference yield:

3,5-dimethoxyphthalic anhydride (4670-17-1) + ortho-cresol (95-48-7,77504-84-8) → emodin-6,8-di-O-methyl ether (5018-84-8) + 3,5-dimethoxy-2-(4-hydroxy-3-methylbenzoyl)benzoic acid (144828-20-6)

Guidance literature:

With aluminium trichloride; at 40 - 160 ℃; for 1h; Title compound not separated from byproducts;

Reference yield: 71.0%

emodin-6,8-di-O-methyl ether (5018-84-8) → emodin-9-anthrone (38371-02-7)

Guidance literature:

With hydrogen iodide; acetic acid; for 3h; Heating;

DOI:10.1128/aac.42.9.2245

upstream raw materials:

3,5-dimethoxyphthalic anhydride

ortho-cresol

3-chloro-5-hydroxy-7-methoxy-1,4-naphthoquinone

(E)-((1-methoxy-3-methylbuta-1,3-dien-1-yl)oxy)trimethylsilane

Downstream raw materials:

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

physcion

emodin-9-anthrone

endocrocin

Refernces

• 1、 Savard, Jacques,Brassard, Paul. "REACTIONS OF KETENE ACETALS-14; THE USE OF SIMPLE MIXED VINYLKETENE ACETALS IN THE ANNULATION OF QUINONES". . p. 3455 - 3464. Retrieved 2007/10/02.