Tetroquinone | CAS# 319-89-1 | Redox-active hydroxyquinone

MedKoo Cat#: 558208 | Name: Tetrahydroxyquinone

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tetrahydroxyquinone is a redox-active hydroxyquinone. It inhibits HIV-1 proteinase and is active against T. brucei brucei. Tetrahydroxyquinone induces the formation of reactive oxygen species (ROS) in, as well as apoptosis of, HL-60 leukemia cells. It has also been used in the manufacturing of lithium-ion batteries.

Chemical Structure

Tetrahydroxyquinone

CAS# 319-89-1 (free base)

Theoretical Analysis

MedKoo Cat#: 558208

Name: Tetrahydroxyquinone

CAS#: 319-89-1 (free base)

Chemical Formula: C6H4O6

Exact Mass: 172.0008

Molecular Weight: 172.09

Elemental Analysis: C, 41.88; H, 2.34; O, 55.78

Price and Availability

Size	Price	Availability	Quantity
5g	USD 450.00	2 Weeks
10g	USD 750.00	2 Weeks

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Related CAS #

319-89-1 (free base) 1887-02-1 (disodium) 5676-48-2 (dihydrate)

Synonym

Tetrahydroxyquinone; Tetroquinone; Tetroquinona; Tetroquinonum; NSC 112931; NSC112931; NSC-112931; THQ;

IUPAC/Chemical Name

2,3,5,6-tetrahydroxycyclohexa-2,5-diene-1,4-dione

InChi Key

DGQOCLATAPFASR-UHFFFAOYSA-N

InChi Code

InChI=1S/C6H4O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h7-8,11-12H

SMILES Code

O=C1C(O)=C(O)C(C(O)=C1O)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 172.09 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Majidi L, Ahmadiparidari A, Shan N, Misal SN, Kumar K, Huang Z, Rastegar S, Hemmat Z, Zou X, Zapol P, Cabana J, Curtiss LA, Salehi-Khojin A. 2D Copper Tetrahydroxyquinone Conductive Metal-Organic Framework for Selective CO2 Electrocatalysis at Low Overpotentials. Adv Mater. 2021 Feb 1:e2004393. doi: 10.1002/adma.202004393. Epub ahead of print. PMID: 33522009. 2: Chen G, Gee LB, Xu W, Zhu Y, Lezama-Pacheco JS, Huang Z, Li Z, Babicz JT Jr, Choudhury S, Chang TH, Reed E, Solomon EI, Bao Z. Valence-Dependent Electrical Conductivity in a 3D Tetrahydroxyquinone-Based Metal-Organic Framework. J Am Chem Soc. 2020 Dec 23;142(51):21243-21248. doi: 10.1021/jacs.0c09379. Epub 2020 Dec 14. PMID: 33315385. 3: Park J, Hinckley AC, Huang Z, Feng D, Yakovenko AA, Lee M, Chen S, Zou X, Bao Z. Synthetic Routes for a 2D Semiconductive Copper Hexahydroxybenzene Metal- Organic Framework. J Am Chem Soc. 2018 Nov 7;140(44):14533-14537. doi: 10.1021/jacs.8b06666. Epub 2018 Oct 30. PMID: 30176142. 4: Lo Cicero M, Della Pia A, Riello M, Colazzo L, Sedona F, Betti MG, Sambi M, De Vita A, Mariani C. A long-range ordered array of copper tetrameric units embedded in an on-surface metal organic framework. J Chem Phys. 2017 Dec 7;147(21):214706. doi: 10.1063/1.5004082. PMID: 29221400. 5: Fouad DM, Ismail NM, El-Gahami MA, Ibrahim SA. Kinetics of the substitution of dehydroacetic acid in tris (dehydroacetato) Fe(III) complex by 8-hydroxyquinoline, di- and tetra-hydroxyquinone. Spectrochim Acta A Mol Biomol Spectrosc. 2007 Jun;67(2):564-7. doi: 10.1016/j.saa.2006.05.039. Epub 2006 Aug 18. PMID: 17049303. 6: Martins Cavagis AD, Ferreira CV, Versteeg HH, Assis CF, Bos CL, Bleuming SA, Diks SH, Aoyama H, Peppelenbosch MP. Tetrahydroxyquinone induces apoptosis of leukemia cells through diminished survival signaling. Exp Hematol. 2006 Feb;34(2):188-96. doi: 10.1016/j.exphem.2005.11.001. PMID: 16459187. 7: Ching R. Tetrahydroxyquinone (THQ): its use in ophthalmology. Eye Ear Nose Throat Mon. 1971 Apr;50(4):144-9. PMID: 5572985. 8: Ching R. Tetrahydroxyquinone (THQ) its use in ophthalmology. I. Eye Ear Nose Throat Mon. 1971 Mar;50(3):101-7 contd. PMID: 5552869. 9: Takeuchi S, Inoue Y. Hypoglycemic actions of tetrahydroxyquinone, rhodizonic acid and trichinoyl in mice and rabbits. Jpn J Pharmacol. 1968 Sep;18(3):312-20. doi: 10.1254/jjp.18.312. PMID: 5304400. 10: Satoh GJ, Kelly EW Jr. Changes in the collagen and acid mucopolysaccharides of rat skin during the calciphylactic calciferol-albumin syndrome and the effect of simultaneous administration of tetrahydroxyquinone. J Invest Dermatol. 1967 Jan;48(1):1-6. doi: 10.1038/jid.1967.1. PMID: 4225134. 11: Keech MK, McCann DS, Boyle AJ, Pinkus H. Effect of ethylenediaminetetraacetic acid (EDTA) and tetrahydroxyquinone on sclerodermatous skin. Histologic and chemical studies. J Invest Dermatol. 1966 Sep;47(3):235-46. doi: 10.1038/jid.1966.136. PMID: 4958819. 12: KELLY EW Jr. TETRAHYDROXYQUINONE (THQ) EFFECTS ON SPONGE IMPLANTS IN THE ALBINO RAT. Arch Pathol. 1964 Mar;77:317-23. PMID: 14095749. 13: KELLY EW Jr. The effects of tetrahydroxyquinone on connective tissue. J Chronic Dis. 1963 Apr;16:335-42. doi: 10.1016/0021-9681(63)90084-5. PMID: 14031813. 14: SERIS JL, BRU A. [The protective effect of tetrahydroxyquinone against the action of x-rays on baker's yeasts]. C R Hebd Seances Acad Sci. 1962 Jul 23;255:791-3. French. PMID: 13910826. 15: PREISLER PW, BERGER L, HILL ES. Oxidation-reduction potentials and ionization constants of the reversible series; hexahydroxybenzene- tetrahydroxyquinone-rhodizonic acid. J Am Chem Soc. 1948 Feb;70(2):871. doi: 10.1021/ja01182a515. PMID: 18933297.