1,2,4,5-Cyclohexanetetrol (also named cyclohexane-1,2,4,5-tetrol, 1,2,4,5-tetrahydroxycyclohexane, or ''para''-cyclohexanetetrol) is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

whose molecule can be described as a

cyclohexane Cyclohexane is a cycloalkane with the molecular formula . Cyclohexane is non-polar. Cyclohexane is a colourless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohexan ...

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 ...

(OH)

groups A group is a number of persons or things that are located, gathered, or classed together. Groups of people * Cultural group, a group whose members share the same cultural identity * Ethnic group, a group whose members share the same ethnic iden ...

substituted for

hydrogen Hydrogen is a chemical element; it has chemical symbol, symbol H and atomic number 1. It is the lightest and abundance of the chemical elements, most abundant chemical element in the universe, constituting about 75% of all baryon, normal matter ...

atoms on two non-adjacent pairs of adjacent

carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...

atoms. Its

formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...

can be written , , or ��(–)₂––sub>2. There are 7

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...

s with this same

structural formula The structural formula of a chemical compound is a graphic representation of the molecular structure (determined by structural chemistry methods), showing how the atoms are connected to one another. The chemical bonding within the molecule is al ...

, which are among the 43 isomers of

cyclohexanetetrol A cyclohexanetetrol is a chemical compound consisting of a cyclohexane molecule with four hydroxyl groups (–OH) replacing four of the twelve hydrogen atoms. It is therefore a cyclitol (cyclic polyol). Its generic formula is or . Some cyclohexane ...

. They are all

polyol In organic chemistry, a polyol is an organic compound containing multiple hydroxyl groups (). The term "polyol" can have slightly different meanings depending on whether it is used in food science or polymer chemistry. Polyols containing two, th ...

s, more specifically

tetrol In organic chemistry, a polyol is an organic compound containing multiple hydroxyl groups (). The term "polyol" can have slightly different meanings depending on whether it is used in food science or polymer chemistry. Polyols containing two, thre ...

s and

cyclitol In organic chemistry, a cyclitol is a cycloalkane containing at least three hydroxyl, each attached to a different ring carbon atom. The general formula for an unsubstituted cyclitol is or where 3 ≤ ''x'' ≤ ''n''. The name is also used for ...

s. Some of them have biologically important roles in some organisms.

Isomers and nomenclature

There are 7 different

s of this compound, that differ in the orientation of the four hydroxyls relative to the mean plane of the ring. They can be denoted by the letter "α" or "β" after each carbon index ("2α","2β","4β", etc.), to indicate the corresponding side of the plane relative to the 1-hydroxyl; or by listing all the "α" indices, then a slash "/", then the "β" indices (or "0" if the second list is empty). The possible isomers are: * 1α,2α,4α,5α-, 1,2,4,5/0-, or all-''cis'', with all hydroxyls on the same side (achiral). * 1α,2α,4α,5β- or 1,2,4/5-, and its enantiomer. * 1α,2α,4β,5β- or 1,2/4,5- (achiral). * 1α,2β,4β,5α- or 1,4/2,5- (achiral). * 1α,2β,4α,5β- or 1,2/4,5-, and its enantiomer.

Synthesis

Methods which have been employed for the preparation of 1,2,4,5-cyclohexanetetrols include: reduction or hydrogenation of (1) tri-hydroxycyclohexanones, (2) hydroxylated aromatics, or (3) hydroxylated quinones; the (4) hydrogenolysis of dibromocyclohexanetetrols; the (5) hydration of diepoxycyclohexanes; and the hydroxylation of (6) cyclohexadienes or (7) cyclohexenediols. In 1998, Ahmet Maras and others reported the synthesis of racemic 1,4/2,5-cyclohexanetetrol (the chiral ''trans''-''trans'' ''para'' isomer) by hydroxyla-tion of

1,4-cyclohexadiene 1,4-Cyclohexadiene is an organic compound with the formula C6H8. It is a colourless, flammable liquid that is of academic interest as a prototype of a large class of related compounds called terpenoids, an example being γ-terpinene. An isomer of ...

with

stoichiometric Stoichiometry () is the relationships between the masses of reactants and products before, during, and following chemical reactions. Stoichiometry is based on the law of conservation of mass; the total mass of reactants must equal the total m ...

amount of

hydrogen peroxide Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscosity, viscous than Properties of water, water. It is used as an oxidizer, bleaching agent, and antiseptic, usua ...

(, 30% in

1-butanol 1-Butanol, also known as butan-1-ol or ''n''-butanol, is a primary alcohol with the chemical formula C4H9OH and a linear structure. Isomers of 1-butanol are isobutanol, butan-2-ol and ''tert''-butanol. The unmodified term butanol usually refers ...

), with

selenium dioxide Selenium dioxide is the chemical compound with the formula SeO2. This colorless solid is one of the most frequently encountered compounds of selenium. It is used in making specialized glasses as well as a reagent in organic chemistry. Properties ...

as catalyzer. The yield was 88%, with no trace of the 1,5/2,4 isomer. The racemic 1,4/2,5 isomer is soluble in

ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...

, and yields colorless crystals with melting point 194–196 °C. The (+) enantiomer is betitol, a natural product first identified in

sugar beet A sugar beet is a plant whose root contains a high concentration of sucrose and that is grown commercially for sugar production. In plant breeding, it is known as the Altissima cultivar group of the common beet (''Beta vulgaris''). Together with ...

s. The pure 1α,2α,4α,5α enantiomer crystallize as a monohydrate in the

monoclinic In crystallography, the monoclinic crystal system is one of the seven crystal systems. A crystal system is described by three Vector (geometric), vectors. In the monoclinic system, the crystal is described by vectors of unequal lengths, as in t ...

C2 group (a = 10.675 Å, b = 7.3502 Å, c = 5.1968 Å, β = 103.877°)

References

CON and CBN IUPAC Commissions on Nomenclature (1968): "The Nomenclature of Cyclitols - Tentative Rules". ''European Journal of Biochemistry'', volume 5, pages 1-12. Nihat Akbulut and Metin Balci (1988): "A new and stereospecific synthesis of cyclitols: (1,2,4/3)-, (1,2/3,4)-, and (1,3/2,4)-cyclohexanetetrols". ''Journal of Organic Chemistry'', volume 53, issue 14, pages 3338-3342. J. S. Craigie (1969): "Some Salinity-Induced Changes in Growth, Pigments, and Cyclohexanetetrol Content of ''Monochrysis lutheri''". ''Journal of the Fisheries Research Board of Canada'', volume 26, issue 11, pages 2959-2967. G. E. McCasland, Stanley Furuta, L. F. Johnson, and J. N. Shoolery (1963): ''Synthesis of the Five Diastereomeric 1,2,4,5-Cyclohexanetetrols. Nuclear Magnetic Resonance Configurational Proofs''. ''Journal of Organic Chemistry'', volume 28, issue 4, pages 894-900. Th. Posternak and H. Friedli (1953): "Recherches dans la série des cyclitols XVI. Sur quelques cyclohexane-tétrols-1,2,3,4". ''Helvetica Chimica Acta'', volume 36, issue 1, pages 251-259. Théodore Posternak and Dominique Reymond (1953): "Recherches dans la série des cyclitols XVII. Sur l'oxydation de divers cyclitols par Acetobacter suboxydans". ''Helvetica Chimica Acta'', volume 36, issue 1, pages 260-268. T. Posternak et al. (1955): ''Helvetica Chimica Acta'', volume 38, pages 208-. T. Posternak and D. Reymond (1955): "Recherches dans la série des cyclitols XXI. Sur la configuration de cyclohexane-tétrols et -triols optiquement actifs. Sur l'oxydation biochimique du cyclohexane-tétrol-1,4/2,3 (dihydro-conduritol)". ''Helvetica Chimica Acta'', volume 38, issue 1, pages 195-205. R. Criegee and P. Becher (1957): ''Chemische Berichte'', volume 90, pages 2516-. Ahmet Maras, Mesut Erden, Hasan Seçen, and Yasar Sütbeyaz (1998): "One-pot synthesis from 1,4-cyclohexadiene of (±)-1,4/2,5-cyclohexanetetrol, a naturally occurring cyclitol derivative". ''Carbohydrate Research'', volume 308, issues 3–4, April , Pages 435-437. G. Mehta, S. Sen and S. Dey (2005). "(1S*,2S*,4S*,5S*)-Cyclohexane-1,2,4,5-tetrol monohydrate". ''Acta Crystallographica'', volume C-61, pages o358-o360. E.O. von Lippmann (1901), ''Chemische Berichte'', volume 34, pages 1159-1162. J.D. Ramanathan, J.S. Craigie, J. McLachlan, D.G. Smith, and A.G. McInnes (1966): ''Tetrahedron Letters'', volume 1966, pages 1527-1531. J. S. Craigie, J. McLachlan, and R. D. Tocher (1968): ''Canadian Journal of Botany'', volume 46, pages 605-611. {{DEFAULTSORT:Cyclohexanetetrol, 1,2,3,4- Tetrols Cyclohexanols