2,5-Dihydroxy-1,4-benzoquinone  (Synonyms: DHBQ)

2,5-Dihydroxy-1,4-benzoquinone (DHBQ) is a redox-active quinone-based organic ligand with antibacterial activity that can be obtained from fungal metabolites. After 2,5-Dihydroxy-1,4-benzoquinone is incorporated into the Fe (dhbq) metal-organic framework, a two-electron redox process occurs, which helps improve the discharge capacity of Li⁺-ion battery cathodes. 2,5-Dihydroxy-1,4-benzoquinone can be used to construct conductive metal-organic frameworks suitable for Li⁺-ion battery cathodes^[1][2].

2,5-Dihydroxy-1,4-benzoquinone (DHBQ) is a redox-active cathode material for lithium-ion batteries (LIBs)^[1]:\n
For instance, as a ligand for constructing Fe (dhbq) complexes, it achieves an initial discharge specific capacity of 264 mA·h·g^-1 via a two-electron redox process, and the capacity retention depends on the content of conductive additives;\n
Alternatively, as a ligand for anhydrous Fe (dhbq) prepared at 180 °C, it exhibits permanent microporosity, a narrower optical band gap, and a room-temperature conductivity of 5×10^-6·S·cm^-1, which is 10⁴ times higher than that of the hydrated form Fe (dhbq)(H₂O)₂.\n

Various derivatives of 2,5-Dihydroxy-1,4-benzoquinone exhibit diverse in vitro antibacterial and cellular activities^[2]. For example:
(1)Polyporic acid(40 μg/mL) inhibits the growth of Bacillus subtilis and Micrococcus luteus;
(2)Atromentin inhibits the growth of Bacteroides succinogenes at 50 μg/mL, suppresses the growth of Butyrivibrio fibrisolvens and Megasphaera elsdenii at 600 μg/mL, and significantly inhibits the production of total volatile acids from glucose fermentation by Selenomonas ruminantium at 40 μg/mL, completely blocks the production of lactic acid and succinic acid, and results in acetic acid accounting for approximately 70% of the total acids. Meanwhile, Atromentin induces the formation of chain-like structures consisting of up to 20 cells from non-filamentous Butyrivibrio fibrisolvens cells at 100 μg/mL, causes Succinivibrio dextrinosolvens cells to arrange in chains and lose their tip structures at 80 μg/mL, and inhibits cell separation of Megasphaera elsdenii to form chain-like structures with 10-30 cells at 400 μg/mL;
(3)Osporein inhibits the growth of Micrococcus luteus at 100 μg/mL;
(4)Bovinone inhibits the growth of Bacillus subtilis and Micrococcus luteus at 10 μg/mL;
(5)Cochliodinol inhibits the growth of Butyrivibrio fibrisolvens and causes approximately 10% of cells to become filamentous at 1 μg/mL, suppresses the growth of Micrococcus luteus at 50 μg/mL, inhibits the growth of Megasphaera elsdenii at 60 μg/mL, and restrains the growth of Mycobacterium smegmatis, Bacteroides succinogenes, Selenomonas ruminantium and Succinivibrio dextrinosolvens while increasing the cell volume of Succinivibrio dextrinosolvens at 200 μg/mL. Meanwhile, Cochliodinol inhibits cell separation of Megasphaera elsdenii to form chain-like structures with 10-30 cells at 20 μg/mL, reduces the production of n-butyric acid, n-valeric acid and n-caproic acid by Megasphaera elsdenii by approximately 75% at 400 μg/mL, decreases the utilization rates of acetic acid and propionic acid, and increases the production of formic acid.

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

140.09

C₆H₄O₄

615-94-1

Solid

Light brown to brown

O=C(C=C1O)C(O)=CC1=O

Room temperature in continental US; may vary elsewhere.

• [1]. Brewer D, et al. The antibacterial activity of some naturally occurring 2, 5-dihydroxy-l, 4-benzoquinones[J]. Canadian journal of microbiology, 1984, 30(8): 1068-1072.

  [2]. Kon K, et al. Electron-Conductive Metal-Organic Framework, Fe(dhbq)(dhbq = 2,5-Dihydroxy-1,4-benzoquinone): Coexistence of Microporosity and Solid-State Redox Activity. ACS Appl Mater Interfaces. 2021;13(32):38188-38193.  [Content Brief]