Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H4O6 |
Molecular Weight | 172.0924 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=C(O)C(=O)C(O)=C(O)C1=O
InChI
InChIKey=DGQOCLATAPFASR-UHFFFAOYSA-N
InChI=1S/C6H4O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h7-8,11-12H
Molecular Formula | C6H4O6 |
Molecular Weight | 172.0924 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/29298374Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/19476355 | https://www.ncbi.nlm.nih.gov/pubmed/8721612
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29298374
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/19476355 | https://www.ncbi.nlm.nih.gov/pubmed/8721612
Tetroquinone (Tetrahydroxy-1,4-benzoquinone, tetrahydroxy-p-benzoquinone, tetrahydroxybenzoquinone) is cyclohexadiene derivative with four hydroxyl groups and two ketone groups in opposite (para) positions, with potent prooxidant activity. The exposure of exponentially growing cultures to Tetroquinone, in the presence of Ca2+, caused a dose-dependent inhibition of cell growth and DNA synthesis. The chemical reactivity of Tetroquinone is strongly similar to those of physiological polyphenols, such as catechols and catecholamines. Despite their physiological and pharmacological roles, these compounds may, in addition, present toxicological properties due to their ability to autoxidize generating ROS and quinones Similar to catechols, the OH-substituents confer to Tetroquinone the ability to autoxidize readily in neutral aqueous solutions generating intermediate superoxide anion radicals, semiquinone radicals, and the corresponding quinone. The compound can be synthesized from glyoxal or from myo-inositol (phytic acid), a natural compound widely present in plants.
Approval Year
Sample Use Guides
Daphnia magna and zebra fish (Brachydanio rerio) were exposured for 2, 4, 6, and 24 h at 1, 3.5, 10, 35, and 100 mg/L.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8721612
V79 Chinese hamster lung fibroblasts cell line was used for activity evaluation. Assays were performed with cells in exponential phase of growth. Cells were seeded in 24-well plates (from Coming), at a density of 3 x l0^4 cells/well, and incubated in complete medium for 44 h. Exposure to Tetroquinone was performed in phosphate-buffered saline (PBS) alone, or containing 1.0 mM CaCl, (PBS/Ca2+), for 30 min at 37°C. THQ solutions were prepared at the desired concentrations immediately before addition to cultures. After treatment, cells were washed twice with PBS and incubated in fresh medium for a further 24-h period. At the end of this growth period cells were lysed with 0.5 M NaOH ( 1.0 ml/well). Cell population was determined by measuring lysate absorbance at 260 nm, a parameter directly correlated with cell number, in the range of 10^5-l0^6 cells.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:10:39 GMT 2023
by
admin
on
Fri Dec 15 15:10:39 GMT 2023
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Record UNII |
U7L4P6H0SU
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C796
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Tetrahydroxy-1,4-benzoquinone
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SUB10952MIG
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DTXSID9045897
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319-89-1
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112931
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206-275-5
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U7L4P6H0SU
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C152579
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m10667
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5424
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CHEMBL1329029
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100000082741
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SOLVATE->ANHYDROUS |
Related Record | Type | Details | ||
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ACTIVE MOIETY |