2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-, methyl ester

Base Information

• Chemical Name: 2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-, methyl ester
• CAS No.: 6155-37-9
• Molecular Formula: C16H10O6
• Molecular Weight: 298.252

Synonyms:4,5-Dihydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-carbonsaeure-methylester;1,3-dihydroxy-anthraquinone-3-carboxylic acid methyl ester;4,5-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid methyl ester;Rheinmethylester;rhein methyl ester;

Chemical Property of 2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-, methyl ester

Chemical Property:

• PSA: 100.90000
• LogP: 1.65980

Purity/Quality:

99% ^*data from raw suppliers

RheinMethylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Rhein Methylate is an intermediate in synthesizing Rhein 8-Glucoside (R318520), which has been seen to exhibit cytotoxic and DNA-damaging properties towards tumor and normal human cells. In addition it has been shown to be an inhibitor of PTP1B (Human Protein Tyrosine Kinase 1B) in vitro. It is an analog of Rhein (318500) which is found in the free state and as glucoside in Rheum spp, Polygonaceae (rhubarb) and in Senna leaves. It is a potential antioxidant resource: endophytic fungi from medicinal plants.

Technology Process of 2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-, methyl ester

There total 10 articles about 2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-, methyl ester 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: 94.0%

4-Hydroxy-5-methoxy-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid methyl ester (80301-53-7) → Rhein methyl ester (6155-37-9)

Guidance literature:

With boron tribromide; In dichloromethane; at -50 ℃; for 7h;

DOI:10.1021/jo00341a050

Reference yield: 93.0%

1,8-dihydroxy-3-carboxy-anthraquinone (478-43-3) + methyl iodide (74-88-4) → Rhein methyl ester (6155-37-9)

Guidance literature:

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 80 ℃;

Reference yield:

methanol (67-56-1) + 1,8-dihydroxy-3-carboxy-anthraquinone (478-43-3) → Rhein methyl ester (6155-37-9)

Guidance literature:

With sulfuric acid;

upstream raw materials:

methanol

1,8-dihydroxy-3-carboxy-anthraquinone

4-Hydroxy-5-methoxy-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid methyl ester

7-methoxy-3-(phenylsulfonyl)-1(3H)-isobenzofuranone

Downstream raw materials:

1,8-dihydroxy-3-carboxy-anthraquinone

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

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