A cyclohexanetetrol is a

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

consisting of 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 ...

molecule 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 (–OH) replacing four of the twelve

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. It is therefore a

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 ...

(cyclic

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 ...

). Its generic formula is or . Some cyclohexanetetrols have biologically important roles in some organisms.

Isomers

There are several cyclohexanetetrol isomers that differ on the position of the hydroxyl groups along the ring, and on their orientation relative to the mean plane of the ring. The isomers with each hydroxyl on a distinct carbon are: *

1,2,3,4-Cyclohexanetetrol 1,2,3,4-Cyclohexanetetrol (also named cyclohexane-1,2,3,4-tetrol, 1,2,3,4-tetrahydroxycyclohexane, or ''ortho''-cyclohexanetetrol) is an organic compound whose molecule can be described as a cyclohexane with four hydroxyl (OH) groups substituted fo ...

or ''ortho''- (10 isomers, including 4

enantiomer In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...

pairs) * 1,2,3,5-Cyclohexanetetrol or ''meta''- (8 isomers, including 2 enantiomer pairs) * 1,2,4,5-Cyclohexanetetrol or ''para''- (7 isomers, including 2 enantiomer pairs) 1,2,3,4-cyclohexanetetrol (generic).png, 1,2,3,4
''ortho'' 1,2,3,5-cyclohexanetetrol (generic).png, 1,2,3,5
''meta'' 1,2,4,5-cyclohexanetetrol (generic).png, 1,2,4,5
''para'' Possible isomers with two

geminal In chemistry, the descriptor geminal () refers to the relationship between two atoms or functional groups that are attached to the same atom. A geminal diol, for example, is a diol (a molecule that has two alcohol functional groups) attached to ...

hydroxyls (on the same carbon) are * 1,1,2,3-Cyclohexanetetrol (4 isomers);

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 ...

of 2,3-dihydroxy-cyclohexanone * 1,1,2,4-Cyclohexanetetrol (4 isomers); hydrate of 2,4-dihydroxy-cyclohexanone * 1,1,3,4-Cyclohexanetetrol (4 isomers); hydrate of 3,4-dihydroxy-cyclohexanone Possible isomers with two pairs of geminal hydroxyls: * 1,1,2,2-Cyclohexanetetrol (1 isomer); twofold hydrate of

1,2-cyclohexanedione 1,2-Cyclohexanedione is an organic compound with the formula . It is one of three isomeric cyclohexanediones. It is a colorless compound that is soluble in a variety of organic solvents. It can be prepared by oxidation of cyclohexanone by sel ...

* 1,1,3,3-Cyclohexanetetrol (1 isomer); twofold hydrate of

1,3-cyclohexanedione 1,3-Cyclohexanedione is an organic compound with the formula (CH2)4(CO)2. It is one of three isomeric cyclohexanediones. It is a colorless compound that occurs naturally. It is the substrate for cyclohexanedione hydrolase. The compound exist ...

* 1,1,4,4-Cyclohexanetetrol (1 isomer); twofold hydrate of 1,4-cyclohexanedione

Preparation

The synthesis of cyclohexanetetrols can be achieved by, among other methods: reduction or hydrogenation of (1)

cyclohexene Cyclohexene is a hydrocarbon with the formula . It is a cycloalkene. At room temperature, cyclohexene is a colorless liquid with a sharp odor. Among its uses, it is an chemical intermediate, intermediate in the commercial synthesis of nylon. Prod ...

tetrols, (2) tri-hydroxycyclohexanones, (3) pentahydroxycyclohexanones, (4) hydroxylated

aromatic hydrocarbon Aromatic compounds or arenes are organic compounds "with a chemistry typified by benzene" and "cyclically conjugated." The word "aromatic" originates from the past grouping of molecules based on odor, before their general chemical properties were ...

s, or (5) hydroxylated

quinone The quinones are a class of organic compounds that are formally "derived from aromatic compounds benzene.html" ;"title="uch as benzene">uch as benzene or naphthalene] by conversion of an even number of –CH= groups into –C(=O)– groups with ...

s; the (6)

hydrogenolysis Hydrogenolysis is a chemical reaction whereby a carbon–carbon or carbon–heteroatom single bond is cleaved or undergoes lysis (breakdown) by hydrogen.Ralph Connor, Homer Adkins. Hydrogenolysis Of Oxygenated Organic Compounds. J. Am. Chem. Soc. ...

of dibromocyclohexanetetrols; the (7) hydration of diepoxycyclohexanes; and the

hydroxylation In chemistry, hydroxylation refers to the installation of a hydroxyl group () into an organic compound. Hydroxylations generate alcohols and phenols, which are very common functional groups. Hydroxylation confers some degree of water-solubility ...

of (8)

cyclohexadiene Cyclohexadiene may refer to: * Cyclohexa-1,3-diene, * Cyclohexa-1,4-diene, See also

* Benzene or its theoretical isomer ''1,3,5-Cyclohexatriene'' * Cyclohexene {{chemistry index ...

s or (9) cyclohexenediols.

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. Fernando Garza‐Sánchez, David J. Chapman, and James B. Cooper (2009): "''Nitzschia Ovalis'' (Bacillariophyceae) Mono Lake strain accumulates 1,4/2,5 cyclohexanetetrol in response to increased salinity". ''Journal of Phycology'', volume 45, issue 2, pages 395-403. 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. {{doi, 10.1021/jo01039a002 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. Z. Zeying and Z. Mingzhe (1987): ''Jiegou Huaxue'', volume 1987, pages 128-131 Z. Zeying and Z. Mingzhe (1988): ''Chemical Abstracts'', page 167846r. Polyols Cyclohexanols