1,4-Dihydroxy-2-(hydroxymethyl)anthracene-9,10-dione

Base Information

• Chemical Name: 1,4-Dihydroxy-2-(hydroxymethyl)anthracene-9,10-dione
• CAS No.: 22296-59-9
• Molecular Formula: C15H10 O5
• Molecular Weight: 270.241
• Hs Code.: 2914690090
• DSSTox Substance ID: DTXSID701043551
• Nikkaji Number: J61.254E
• Wikidata: Q105143641
• ChEMBL ID: CHEMBL34584
• Mol file: 22296-59-9.mol

Synonyms:22296-59-9;1,4-dihydroxy-2-(hydroxymethyl)anthracene-9,10-dione;1,4-Dihydroxy-2-hydroxymethyl-anthraquinone;1,4-Dihydroxy-2-(hydroxymethyl)anthraquinone;Digiferrol;1,4-Dihydroxy-2-hydroxymethylanthraquinone;CHEMBL34584;DTXSID701043551;SB35556;CS-0449743;1,4-Dihydroxy-2-(hydroxymethyl)anthra-9,10-quinone #;9,10-Anthracenedione, 1,4-dihydroxy-2-(hydroxymethyl)-

Chemical Property of 1,4-Dihydroxy-2-(hydroxymethyl)anthracene-9,10-dione

Chemical Property:

• PSA: 94.83000
• LogP: 1.36550
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 270.05282342
• Heavy Atom Count: 20
• Complexity: 421

Purity/Quality:

98.5% ^*data from raw suppliers

1,4-Dihydroxy-2-hydroxymethyl-anthraquinone 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)C3=C(C=C(C(=C3C2=O)O)CO)O

Technology Process of 1,4-Dihydroxy-2-(hydroxymethyl)anthracene-9,10-dione

There total 7 articles about 1,4-Dihydroxy-2-(hydroxymethyl)anthracene-9,10-dione 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: 44.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 1,4-dihydroxy-9,10-anthracenedione (81-64-1,103220-12-8) → digiferrol (22296-59-9)

Guidance literature:

1,4-dihydroxy-9,10-anthracenedione; With sodium dithionite; sodium hydroxide; In methanol; water; at 0 ℃; for 0.166667h; Inert atmosphere;

formaldehyd; In methanol; water; at 0 ℃; for 3h; Inert atmosphere;

With dihydrogen peroxide; In methanol; water; for 0.166667h; Cooling;

DOI:10.1002/ejoc.201300891

Reference yield:

9,10-dihydroxy-2-hydroxymethyl-2,3-dihydro-anthracene-1,4-dione → digiferrol (22296-59-9)

Guidance literature:

With air; In tetrahydrofuran; at 0 ℃; for 0.166667h; Yield given;

Reference yield:

2-Hydroxymethyl-anthracene-1,4,9,10-tetraol → digiferrol (22296-59-9)

Guidance literature:

With oxygen; In ethanol; water; for 0.5h; Yield given;

DOI:10.1246/bcsj.53.3007

upstream raw materials:

1,4-dihydroxy-9,10-anthracenedione

9,10-Dihydroxy-2,3-dihydro-anthracene-1,4-dione

formaldehyd

Downstream raw materials:

1,4-dihydroxy-2-<(2-deoxy-2-amino-β-D-glucosyloxy)methyl>-9,10-dihydro-9,10-anthracenedione

1,2,4-trihydroxy-9,10-anthraquinone

Refernces

• 1、 Bingham, Steve J.,Tyman, John H. P.,Malik, K. M. A.,Hibbs, David E.,Hursthouse, Michael B.. "C-Alkylation of Methyl leuco 6-deoxykermesate by Aldol Reactions and its Application to Synthesis of Carminic acid (the colourant principle of cochineal)". . p. 2465 - 2496. Retrieved 2007/10/03.