Tetrahydroxy-1,4-benzoquinone, also called tetrahydroxy-''p''-benzoquinone, tetrahydroxybenzoquinone, or tetrahydroxyquinone (THBQ, THQ), is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with formula . Its molecular structure consists of a

cyclohexadiene Cyclohexadiene may refer to: * 1,3-Cyclohexadiene, * 1,4-Cyclohexadiene, See also * Benzene or its theoretical isomer ''1,3,5-Cyclohexatriene'' * Cyclohexene Cyclohexene is a hydrocarbon with the formula C6H10. This cycloalkene is a colorle ...

ring with four

hydroxyl In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

groups and two

ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...

groups in opposite (''para'') positions. The compound gives a light red solution in water, and crystallizes as the glistening bluish-black (but non-conducting)

dihydrate In chemistry, a hydrate is a substance that contains water or its constituent elements. The chemical state of the water varies widely between different classes of hydrates, some of which were so labeled before their chemical structure was understo ...

. The compound can be synthesized from

glyoxal Glyoxal is an organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of ...

or from ''myo''-inositol, a natural compound widely present in plants. THBQ forms an

adduct An adduct (from the Latin ''adductus'', "drawn toward" alternatively, a contraction of "addition product") is a product of a direct addition of two or more distinct molecules, resulting in a single reaction product containing all atoms of all co ...

with 4,4′-bipyridine in a 2:3 ratio.

Salts of THBQ

Like most

phenol Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it req ...

s, THBQ is

acid In computer science, ACID ( atomicity, consistency, isolation, durability) is a set of properties of database transactions intended to guarantee data validity despite errors, power failures, and other mishaps. In the context of databases, a sequ ...

ic and easily loses the four

hydrogen ions A hydrogen ion is created when a hydrogen atom loses or gains an electron. A positively charged hydrogen ion (or proton) can readily combine with other particles and therefore is only seen isolated when it is in a gaseous state or a nearly particle ...

from the

groups, yielding anions such as and . The latter is symmetric and

aromatic In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...

, as the

double bond In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betw ...

s and negative charges are evenly distributed over the six CO groups. The

calcium Calcium is a chemical element with the symbol Ca and atomic number 20. As an alkaline earth metal, calcium is a reactive metal that forms a dark oxide-nitride layer when exposed to air. Its physical and chemical properties are most similar to ...

salt is the dark purple pigment produced from inositol by '' Chromohalobacter beijerinckii'' in the fermentation of salt

bean A bean is the seed of several plants in the family Fabaceae, which are used as vegetables for human or animal food. They can be cooked in many different ways, including boiling, frying, and baking, and are used in many traditional dishes th ...

s, already noted by T. Hof in 1935. The dark purple and insoluble dipotassium salt was prepared by Preisler and

Berger Berger is a surname in both German language, German and French language, French, although there is no etymological connection between the names in the two languages. The French surname is an occupational name for a shepherd, from Old French ''bergi ...

in 1942, by oxidizing

inositol Inositol, or more precisely ''myo''-inositol, is a carbocyclic sugar that is abundant in the brain and other mammalian tissues; it mediates cell signal transduction in response to a variety of hormones, neurotransmitters, and growth factors and ...

with

nitric acid Nitric acid is the inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but older samples tend to be yellow cast due to decomposition into oxides of nitrogen. Most commercially available nitri ...

and reacting the result with

potassium carbonate Potassium carbonate is the inorganic compound with the formula K2 CO3. It is a white salt, which is soluble in water. It is deliquescent, often appearing as a damp or wet solid. Potassium carbonate is mainly used in the production of soap and gl ...

in the presence of oxygen. Reaction of this salt with

hydrochloric acid Hydrochloric acid, also known as muriatic acid, is an aqueous solution of hydrogen chloride. It is a colorless solution with a distinctive pungent smell. It is classified as a strong acid Acid strength is the tendency of an acid, symbol ...

produces THBQ in good yield. The black tetrapotassium salt was prepared by

West West or Occident is one of the four cardinal directions or points of the compass. It is the opposite direction from east and is the direction in which the Sunset, Sun sets on the Earth. Etymology The word "west" is a Germanic languages, German ...

and Niu in 1962, by reacting THBQ with potassium

methoxide In organic chemistry, methoxides are organic salts with a anion. They are the simplest alkoxides. Sodium methoxide and potassium methoxide have widespread use, though other metal-cation variants such as lithium methoxide, rubidium methoxide, ...

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a ...

. The salt is diamagnetic and the infrared spectrum suggests that the C–C and C–O distances are all equal, with the ring slightly distorted in the "chair" conformation. Partial oxidation of affords a green, strongly

paramagnetic Paramagnetism is a form of magnetism whereby some materials are weakly attracted by an externally applied magnetic field, and form internal, induced magnetic fields in the direction of the applied magnetic field. In contrast with this behavior, d ...

solid, conjectured to be , and complete oxidation yields potassium rhodizonate . The greenish-black

sodium Sodium is a chemical element with the symbol Na (from Latin ''natrium'') and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable iso ...

salt was described by Fatiadi and Sanger in 1962. The dark-violet

lithium Lithium (from el, λίθος, lithos, lit=stone) is a chemical element with the symbol Li and atomic number 3. It is a soft, silvery-white alkali metal. Under standard conditions, it is the least dense metal and the least dense solid el ...

salt has been proposed as an electrode material for

batteries Battery most often refers to: * Electric battery, a device that provides electrical power * Battery (crime), a crime involving unlawful physical contact Battery may also refer to: Energy source *Automotive battery, a device to provide power t ...

as it can be oxidized to the rhodizonate and reduced to the

hexahydroxybenzene Benzenehexol, also called hexahydroxybenzene, is an organic compound with formula or . It is a six-fold Phenols, phenol of benzene. The product is also called hexaphenol, but this name has been used also for other substances. Benzenehexol is a c ...

salt . In the absence of oxygen, is stable to about 450 °C and then decomposes leaving a residue of

lithium carbonate Lithium carbonate is an inorganic compound, the lithium salt (chemistry), salt of carbonate with the chemical formula, formula . This white Salt (chemistry), salt is widely used in the processing of metal oxides. It is listed on the World Health O ...

. Indeed, the rhodizonate appears to

disproportionate In chemistry, disproportionation, sometimes called dismutation, is a redox reaction in which one compound of intermediate oxidation state converts to two compounds, one of higher and one of lower oxidation states. More generally, the term can ...

at about 400 °C into and

cyclohexanehexone Cyclohexanehexone, also known as hexaketocyclohexane and triquinoyl, is an organic compound with formula , the sixfold ketone of cyclohexane. It is an oxide of carbon (an oxocarbon), a hexamer of carbon monoxide. The compound is expected to be ...

that promptly decomposes into

carbon monoxide Carbon monoxide (chemical formula CO) is a colorless, poisonous, odorless, tasteless, flammable gas that is slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the simple ...

carbon dioxide Carbon dioxide (chemical formula ) is a chemical compound made up of molecules that each have one carbon atom covalently double bonded to two oxygen atoms. It is found in the gas state at room temperature. In the air, carbon dioxide is transpar ...

, and carbon. forms a

hydrate In chemistry, a hydrate is a substance that contains water or its constituent elements. The chemical state of the water varies widely between different classes of hydrates, some of which were so labeled before their chemical structure was understo ...

that loses its water at about 250 °C.

References

{{reflist Organic acids 1,4-Benzoquinones Tetrols Hydroxybenzoquinones Polyphenols