Tetrahydroxyquinone monohydrate (Tetrahydroxy-1,4-benzoquinone monohydrate), an anticataract agent, is a redox-active benzoquinone. Tetrahydroxyquinone monohydrate can participate in redox cycles with semiquinone radicals, leading to the formation of reactive oxygen species (ROS).

Physicochemical Properties

Molecular Formula	C6H6O7
Molecular Weight	190.107642650604
Exact Mass	190.011
CAS #	1215458-51-7
Related CAS #	Tetrahydroxyquinone;319-89-1
PubChem CID	6420048
Appearance	Brown to black solid powder
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	0
Heavy Atom Count	13
Complexity	272
Defined Atom Stereocenter Count	0
InChi Key	CJFTUKFVMMYYHH-UHFFFAOYSA-N
InChi Code	InChI=1S/C6H4O6.H2O/c7-1-2(8)4(10)6(12)5(11)3(1)9;/h7-8,11-12H;1H2
Chemical Name	2,3,5,6-tetrahydroxycyclohexa-2,5-diene-1,4-dione;hydrate
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro

Tetrahydroxyquinone (100-500 μM; 24 hours; HL60 cells) treatment exhibits cytotoxicity for HL60 leukemia cells as measured by MTT assay (IC50 of 45 µM), total protein content (IC50 of 20 µM), or phosphatase activity (IC50 of 40 µM). In HL60 leukaemia cells, tetrahydroxyquinone effectively induces the generation of ROS[1]. At concentrations greater than 25 µM, tetrahydroxyquinone effectively activates caspase 3, induces DNA fragmentation at the same concentration, and causes exposure to phosphatidylserine[1]. Even at 25 µM concentration, tetrahydroxyquinone causes the mitochondria to release cytochrome c. Moreover, treatment with tetrahydroxyquinone increases protein kinase B's phosphorylation of Ser473 (the Bad kinase for Ser112)[1].

References

[1]. Alexandre D Martins Cavagis, et al. Tetrahydroxyquinone induces apoptosis of leukemia cells through diminished survival signaling. Exp Hematol. 2006 Feb;34(2):188-96.

Solubility Data

Solubility (In Vitro)

DMSO : 100 mg/mL (526.01 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (13.15 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (13.15 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	5.2601 mL	26.3006 mL	52.6011 mL
	5 mM	1.0520 mL	5.2601 mL	10.5202 mL
	10 mM	0.5260 mL	2.6301 mL	5.2601 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.