1,4-Anthraquinone

Base Information

• Chemical Name: 1,4-Anthraquinone
• CAS No.: 635-12-1
• Molecular Formula: C14H8O2
• Molecular Weight: 208.216
• Hs Code.: 2914690090
• European Community (EC) Number: 211-228-7
• NSC Number: 104530
• DSSTox Substance ID: DTXSID10212899
• Nikkaji Number: J6.908F
• Wikidata: Q83088128
• Mol file: 635-12-1.mol

Synonyms:1,4-anthraquinone

Chemical Property of 1,4-Anthraquinone

Chemical Property:

• Appearance/Colour: orange brown solid
• Vapor Pressure: 8.39E-07mmHg at 25°C
• Melting Point: 217 °C
• Refractive Index: 1.702
• Boiling Point: 406 °C at 760 mmHg
• Flash Point: 152 °C
• PSA: 34.14000
• Density: 1.328 g/cm³
• LogP: 2.77500
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Insoluble in water.
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 208.052429494
• Heavy Atom Count: 16
• Complexity: 322

Purity/Quality:

97% ^*data from raw suppliers

Anthracene-1,4-dione ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C=C3C(=O)C=CC(=O)C3=CC2=C1
• General Description: 1,4-ANTHRAQUINONE is a structural framework identified in naturally occurring compounds such as Viocristin, Isoviocristin, and Hydroxyviocristin, which were isolated from the fungus *Aspergillus cristatus*. These 1,4-anthraquinone derivatives, previously unreported in nature, exhibit unique chemical properties and potential antimicrobial activities. Their structures were confirmed through spectroscopic analysis and synthetic approaches, highlighting their significance in natural product chemistry and potential biomedical applications.

Technology Process of 1,4-Anthraquinone

There total 30 articles about 1,4-Anthraquinone 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: 98.0%

1,4-dihydroxy-9,10-anthracenedione (81-64-1,103220-12-8) → 1,4-anthraquinone (635-12-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; for 24h; Heating;

DOI:10.1039/P19810000689

Reference yield: 95.0%

C20H14O4 → 1,4-anthraquinone (635-12-1)

Guidance literature:

With triethylamine; In chloroform; at 20 ℃; for 1h;

DOI:10.1016/j.crci.2014.01.024

Reference yield: 75.0%

1,4,4a,9a-tetrahydro-9,10-dioxo-1,4-methanoanthracene-11-spiro-1'-cyclopropane (71155-60-7) → 1,4-anthraquinone (635-12-1)

Guidance literature:

In acetonitrile; for 12h; Heating;

DOI:10.1039/b604063b

upstream raw materials:

1-hydroxyanthracene

1,4-dihydroxy-9,10-anthracenedione

oxalic acid

1,2-bis(dibromomethyl)benzene

Downstream raw materials:

5,12-naphthacenequinone

tetraceno[2,3-b]thiophene-5,12-dione

1,4-dihydroxyanthracene

1,2,3,4-tetrahydroanthracene

Refernces

Metabolic products of microorganisms. 214. Viocristin, isoviocristin, and hydroxyviocristin. Structure and synthesis of naturally occurring 1,4-anthraquinones

10.1002/jlac.198219821210

The research focuses on the metabolic products of the fungus Aspergillus cristatus, specifically the identification and synthesis of naturally occurring 1,4-anthraquinones, including Viocristin (19a), Isoviocristin (18a), and Hydroxyviocristin (13). These compounds are unique as they belong to the 1,4-anthraquinone series, which had not been previously found in nature. The study involved the isolation of these pigments from the mycelium of A. cristatus and detailed their chemical structures through various spectroscopic methods, such as mass spectrometry, 'H-NMR, and IR spectroscopy. The researchers also synthesized these compounds and several model compounds to confirm their structures and to explore their biological activities. Key chemicals involved in the research include Acetanhydride, Methyliodide, Sodium hydroxide, and Dimethyl sulfoxide, which were used in various reactions to synthesize and modify the anthraquinones. The research also utilized solvents like Chloroform, Methanol, and Ethyl acetate for dissolving and crystallizing the compounds. The study provides insights into the biosynthetic pathways of these compounds and their potential applications, particularly in the context of their antimicrobial properties demonstrated in the plate diffusion test.