1,4,5,8-TETRAHYDROXYANTHRAQUINONE

• CAS: 81-60-7
• Catalog Number: ACM81607
• Category: Main Products
• Molecular Weight: 272.21
• Molecular Formula: C14H8O6
• Synonyms: 1,4,5,8-Leucotetraoxyanthraquinone
• Appearance: White solid

Case Study

1,4,5,8-Tetrahydroxyanthraquinone as a Precursor for a High-Voltage Organic Lithium Salt Cathode

Huang, Liang, et al. Chemical Engineering Journal 481 (2024): 148447.

1,4,5,8-Tetrahydroxyanthraquinone (THAQ) is a highly conjugated, symmetric quinone derivative. It serves as the key precursor for synthesising the trilithium salt Li3THAQ, which exhibits exceptional structural stability and electrochemical performance as an organic cathode material for rechargeable lithium metal and lithium-ion batteries.
Synthesis: Li3THAQ was prepared via a simple acid-base neutralisation reaction of THAQ with a lithium base. Although the tetralithium salt was expected, the product was identified as the trilithium salt. Li3THAQ possesses a layered crystalline structure with large interlayer spacings, which remains stable during reversible conversion between Li4THAQ and Li2THAQ.
Performance Evaluation: When tested as a cathode in lithium batteries (2.0-3.6 V), Li3THAQ delivered a high reversible capacity of 192 mAh/g, an average discharge potential of 2.93 V vs. Li+/Li, and 75% capacity retention at 5000 mA/g compared with 50 mA/g. After 500 cycles, 95% of the initial capacity was retained. The material also paired successfully with a natural graphite anode to form a lithium-ion full cell, a rare demonstration for organic lithium salts.

1,4,5,8-Tetrahydroxyanthraquinone as a Potent Inhibitor of Hepatitis C Virus NS3 Helicase

Furuta, Atsushi, et al. International journal of molecular sciences 16.8 (2015): 18439-18453.

1,4,5,8-Tetrahydroxyanthraquinone is a highly conjugated, symmetric hydroxyanthraquinone. It acts as a potent inhibitor of the hepatitis C virus (HCV) NS3 helicase, an essential enzyme for viral replication, by blocking RNA unwinding, ATP hydrolysis and RNA binding. Among a series of hydroxyanthraquinones tested, this compound exhibited the strongest inhibitory activity, with an IC50 value of 6 μM.
Experimental Protocol: A fluorescence resonance energy transfer (FRET)-based helicase assay was used. The double-stranded RNA substrate consisted of a 5'-Alexa Fluor 700-labelled strand annealed to a 3'-Black Hole Quencher-3-labelled complementary strand. The reaction mixture (20 μL) contained 50 nM dsRNA substrate, 400 nM capture strand, 5 mM ATP, 240 nM full-length HCV NS3 protein, and serial dilutions of the test compound in DMSO. The reaction was started by adding NS3 and incubated at 37 °C for 30 min. Fluorescence increase due to strand separation was monitored, and IC50 values were calculated by fitting the dose-response curves.
Performance Evaluation: 1,4,5,8-Tetrahydroxyanthraquinone inhibited NS3 helicase with an IC50 of 6 μM, significantly stronger than 1,4-dihydroxyanthraquinone (IC50 = 54 μM) and other regioisomers (IC50 > 200 μM). Its activity was also higher than trihydroxyanthraquinones (IC50 = 11-18 μM). The compound possesses four keto-phenol systems, each pair sharing a ketone group on the same benzene ring, a structural feature critical for inhibition.

Custom Q&A

What is the molecular formula of 1,4,5,8-tetrahydroxyanthraquinone?

The molecular formula of 1,4,5,8-tetrahydroxyanthraquinone is C14H8O6.

What is the molecular weight of 1,4,5,8-tetrahydroxyanthraquinone?

The molecular weight of 1,4,5,8-tetrahydroxyanthraquinone is 272.21 g/mol.

What is another name for 1,4,5,8-tetrahydroxyanthraquinone?

Another name for 1,4,5,8-tetrahydroxyanthraquinone is 1,4,5,8-tetrahydroxyanthracene-9,10-dione.

What is the CAS number of 1,4,5,8-tetrahydroxyanthraquinone?

The CAS number of 1,4,5,8-tetrahydroxyanthraquinone is 81-60-7.

What is the InChIKey of 1,4,5,8-tetrahydroxyanthraquinone?

The InChIKey of 1,4,5,8-tetrahydroxyanthraquinone is SOGCSKLTQHBFLP-UHFFFAOYSA-N.

How many hydrogen bond donor counts does 1,4,5,8-tetrahydroxyanthraquinone have?

1,4,5,8-tetrahydroxyanthraquinone has 4 hydrogen bond donor counts.

How many hydrogen bond acceptor counts does 1,4,5,8-tetrahydroxyanthraquinone have?

1,4,5,8-tetrahydroxyanthraquinone has 6 hydrogen bond acceptor counts.

How many rotatable bond counts does 1,4,5,8-tetrahydroxyanthraquinone have?

1,4,5,8-tetrahydroxyanthraquinone has 0 rotatable bond counts.

What is the topological polar surface area of 1,4,5,8-tetrahydroxyanthraquinone?

The topological polar surface area of 1,4,5,8-tetrahydroxyanthraquinone is 115Ų.

Is 1,4,5,8-tetrahydroxyanthraquinone a canonicalized compound?

Yes, 1,4,5,8-tetrahydroxyanthraquinone is a canonicalized compound.