Catenarin

Base Information

• Chemical Name: Catenarin
• CAS No.: 476-46-0
• Molecular Formula: C15H10 O6
• Molecular Weight: 286.241
• NSC Number: 344022
• UNII: EHN5P96V6S
• DSSTox Substance ID: DTXSID50197212
• Nikkaji Number: J12.544J
• Wikidata: Q83070157
• Metabolomics Workbench ID: 130083
• ChEMBL ID: CHEMBL29860
• Mol file: 476-46-0.mol

Synonyms:4-hydroxyemodin

Chemical Property of Catenarin

Chemical Property:

• Vapor Pressure: 1.9E-16mmHg at 25°C
• Melting Point: 246℃
• Boiling Point: 629.6°Cat760mmHg
• Flash Point: 348.6°C
• PSA: 115.06000
• Density: 1.693g/cm³
• LogP: 1.59280
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 286.04773803
• Heavy Atom Count: 21
• Complexity: 463

Purity/Quality:

99%, ^*data from raw suppliers

1,4,6,8-Tetrahydroxy-3-methylanthraquinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C2C(=C1O)C(=O)C3=C(C2=O)C(=CC(=C3)O)O)O
• Uses: 1,4,6,8-Tetrahydroxy-3-methylanthraquinone is an anthraquinones in the fungus Talaromyces stipitatus.

Technology Process of Catenarin

There total 17 articles about Catenarin 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: 91.0%

Rubrocristin-β-benzylether (84542-37-0) → catenarin (476-46-0) + rubrocristin (74815-59-1)

Guidance literature:

With boron trichloride; In dichloromethane; chloroform; for 0.0333333h;

DOI:10.1002/jlac.198219821210

Reference yield:

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone (518-82-1) → 7-hydroxyemodin (10228-40-7) + catenarin (476-46-0)

Guidance literature:

With N-Acetylcysteine; recombinant human P₄₅₀ enzyme 1A₂; NADPH; at 37 ℃; for 0.5h; Enzymatic reaction;

DOI:10.1021/acs.chemrestox.6b00191

Reference yield:

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone (518-82-1) → citreorosein (481-73-2) + 7-hydroxyemodin (10228-40-7) + catenarin (476-46-0)

Guidance literature:

With N-Acetylcysteine; recombinant human P₄₅₀ enzyme 3A₄; NADPH; at 37 ℃; for 0.5h; Enzymatic reaction;

DOI:10.1021/acs.chemrestox.6b00191

upstream raw materials:

2-(5-bromo-2-hydroxy-4-methyl-benzoyl)-3,5-dimethoxy-benzoic acid

5,7-Diethoxy-1,4-dihydroxy-2-methyl-anthraquinone

3,5-dimethoxyphthalic anhydride

1-bromo-2,5-dimethoxy-3-methylbenzene

Downstream raw materials:

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

oxalic acid

7-Benzyloxy-4,5-dihydroxy-1-methoxy-2-methyl-9,10-anthrachinon

Rubrocristin-β-benzylether

Refernces

• 1、 Qin, Boyang,Xu, Yang,Chen, Jiaming,Huang, Wenlin,Peng, Ying,Zheng, Jiang. "Chemical Reactivity of Emodin and Its Oxidative Metabolites to Thiols". . p. 2114 - 2124. Retrieved 2016/12/26.
• 2、 Laatsch,Anke. "Metabolic products of microorganisms. 214. Viocristin, isoviocristin, and hydroxyviocristin. Structure and synthesis of naturally occurring 1,4-anthraquinones". . p. 2189 - 2215. Retrieved 2007/10/02.