A cyclohexanetetrol is a chemical compound consisting of a

cyclohexane Cyclohexane is a cycloalkane with the molecular formula . Cyclohexane is non-polar. Cyclohexane is a colorless, 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 the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-toxic, an ...

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 c ...

(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, thr ...

). 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 ( /ɪˈnænti.əmər, ɛ-, -oʊ-/ ''ih-NAN-tee-ə-mər''; from Ancient Greek ἐνάντιος ''(enántios)'' 'opposite', and μέρος ''(méros)'' 'part') – also called optical isomer, antipode, or optical ant ...

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 * 1,1,3,3-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 C6H10. This cycloalkene is a colorless liquid with a sharp smell. It is an intermediate in various industrial processes. Cyclohexene is not very stable upon long term storage with exposure to light an ...

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

aromatic hydrocarbon Aromatic compounds, also known as "mono- and polycyclic aromatic hydrocarbons", are organic compounds containing one or more aromatic rings. The parent member of aromatic compounds is benzene. The word "aromatic" originates from the past grouping ...

s, or (5) hydroxylated

quinone The quinones are a class of organic compounds that are formally "derived from aromatic compounds

uch as benzene or naphthalene Uch ( pa, ; ur, ), frequently referred to as Uch Sharīf ( pa, ; ur, ; ''"Noble Uch"''), is a historic city in the southern part of Pakistan's Punjab province. Uch may have been founded as Alexandria on the Indus, a town founded by Alexand ...

by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of double ...

s; the (6) hydrogenolysis of dibromocyclohexanetetrols; the (7) hydration of diepoxycyclohexanes; and the hydroxylation of (8)

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 ...

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