In organic chemistry, a cyclitol is a cycloalkane containing at least three hydroxyl, each attached to a different ring carbon atom.
The name is also used for compounds that can be viewed as result of substituting various for the hydrogen atoms in such a molecule, as well as similar molecules with one or more in the ring.
Cyclitols and their derivatives are some of the osmoprotectant which are formed in a plant as a response to salt or water stress. Some cyclitols (e.g. quinic acid or shikimic acid) are parts of hydrolysable tannins.
Isomerism and nomenclature
Unsubstituted cyclitols with the same ring size and number of hydroxyls may exist in several structural isomers, depending on the position of the hydroxyls along the ring. For example, cyclohexanetriol exists in three distinct isomers (1,2,3-, 1,2,4-, and 1,3,5-).
Furthermore, the hydrogen and the hydroxyl on each carbon atom may lie in two possible arrangements relative to the local ring plane; so that each structural isomer may exist in several , depending on which side of the ring plane the hydroxyls are. For example, there are nine stereoisomers of 1,2,3,4,5,6-cyclohexanehexol (inositol), and two of them are . The IUPAC has provided a nomenclature for cyclitol stereoisomers.[CON and CBN IUPAC Commissions on Nomenclature (1968): "The Nomenclature of Cyclitols - Tentative Rules". European Journal of Biochemistry, volume 5, pages 1-12. ]
Naturally occurring cyclitols
Unsubstituted
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Conduritol, or cyclohex-5-ene-1,2,3,4-tetrol; two out of ten possible isomers.
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Inositol, or cyclohexane-1,2,3,4,5,6-hexol; four out of nine possible isomers.
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Cyclohexanetetrol
[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. ]
Substituted
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Bornesitol; (1R,2R,3S,4S,5R,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol; D-(−)-O-methyl- myo-inositol
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Pinitol; (1S,2S,4S,5R)-6-methoxycyclohexane-1,2,3,4,5-pentol; 3-O-methyl-D- chiro-inositol
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Ononitol; (1R,2S,3S,4S,5S,6S)-6-methoxycyclohexane-1,2,3,4,5-pentaol; 4-O-methyl- myo-inositol
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Pinpollitol; (1R,2R,3R,4S,5R,6S)-3,6-dimethoxycyclohexane-1,2,4,5-tetraol; di-O-methyl-(+)- chiro-inositol
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Quebrachitol; (1R,2S,4S,5R)-6-methoxycyclohexane-1,2,3,4,5-pentol; 2-0-methyl- chiro-inositol
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Quinic acid; (1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid
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Shikimic acid; (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
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Valienol; (1S,2S,3S,4R)-5-(Hydroxymethyl)cyclohex-5-ene-1,2,3,4-tetrol
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Viscumitol (1R,2S,3R,4S,5R,6S)-5,6-dimethoxycyclohexane-1,2,3,4-tetraol; 1,2-di-O-methyl- muco-inositol
Glycosides
Phosphates
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Phytic acid; (1R,2S,3r,4R,5S,6s)-cyclohexane-1,2,3,4,5,6-hexayl hexakisdihydrogen(phosphate); inositol hexakisphosphate
Other cyclitols
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1,2,3,4-Cyclohexanetetrol
[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. ]
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1,2,3,4,5-Cyclopentanepentol
Analysis methods
In 1955, Posternak and others described the separation of cyclitols by paper chromatography in various solvents, and three methods of development:
, the Meillère reagent (based on the Scherer-Gallois reaction), and digestion by
Acetobacter suboxydans followed by Tollens reagent.
[Th. Posternak, D. Reymond, W. Haerdi (1955): "Recherches dans la série des cyclitols XX. Chromatographie sur papier de cyclitols et de cycloses". Helvetica Chimica Acta volume 38, issue 1, pages 191-194 ]
See also
External links
