Cyclitol
In organic chemistry, a cyclitol is a cycloalkane containing at least three hydroxyl, each attached to a different ring carbon atom.[1] Most commonly, cyclitol refers to cyclic sugar alcohol.[2] Cyclitols and their derivatives are some of the compatible solutes that are formed in a plant as a response to salt or water stress. Cyclitols are minor components of trees.[3] Some cyclitols (e.g. quinic or shikimic acid) are parts of hydrolysable tannins.
Even simple cyclitols can be complicated from the perspective of stereochemistry. For example, cyclohexanetriol exists in three isomers (1,2,3-, 1,2,4-, and 1,3,5-). Furthermore, nine stereoisomers are possible for 1,2,3,4,5,6-cyclohexanehexol (inositol), two of them being enantiomers.
Naturally occurring cyclitols
[edit | edit source]Unsubstituted
[edit | edit source]- Conduritol, or cyclohex-5-ene-1,2,3,4-tetrol; two out of ten possible isomers.
- Inositol, or cyclohexane-1,2,3,4,5,6-hexol; four out of nine possible isomers.
- Cyclohexanetetrol[4]
Substituted
[edit | edit source]- Bornesitol; (1R,2R,3S,4S,5R,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol; D-(−)-O-methyl-myo-inositol
- Pinitol; (1S,2S,4S,5R)-6-methoxycyclohexane-1,2,3,4,5-pentol; 3-O-methyl-D-chiro-inositol
- Ononitol; (1R,2S,3S,4S,5S,6S)-6-methoxycyclohexane-1,2,3,4,5-pentaol; 4-O-methyl-myo-inositol
- Pinpollitol; (1R,2R,3R,4S,5R,6S)-3,6-dimethoxycyclohexane-1,2,4,5-tetraol; di-O-methyl-(+)-chiro-inositol
- Quebrachitol; (1R,2S,4S,5R)-6-methoxycyclohexane-1,2,3,4,5-pentol; 2-0-methyl-chiro-inositol
- Quinic acid; (1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid
- Shikimic acid; (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
- Valienol; (1S,2S,3S,4R)-5-(Hydroxymethyl)cyclohex-5-ene-1,2,3,4-tetrol
- Viscumitol (1R,2S,3R,4S,5R,6S)-5,6-dimethoxycyclohexane-1,2,3,4-tetraol; 1,2-di-O-methyl-muco-inositol
Glycosides
[edit | edit source]- Ciceritol, a pinitol digalactoside
Phosphates
[edit | edit source]- Phytic acid; (1R,2S,3r,4R,5S,6s)-cyclohexane-1,2,3,4,5,6-hexayl hexakis[dihydrogen(phosphate)]; inositol hexakisphosphate
Other cyclitols
[edit | edit source]Applications
[edit | edit source]Aside from their utility to plants, cyclitols are useful as precursors to synthetic materials.[6]
Analysis methods
[edit | edit source]Théodore Posternak and others described the separation of cyclitols by paper chromatography using three methods of development: Tollens' reagents, the Meillère reagent (based on the Scherer-Gallois reaction), and digestion by Acetobacter suboxydans followed by Tollens' reagent.[7]
Further reading
[edit | edit source]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. Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
See also
[edit | edit source]References
[edit | edit source]- ^ IUPAC, Compendium of Chemical Terminology, 5th ed. (the "Gold Book") (2025). Online version: (2006–) "Cyclitols". Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ 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. Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ 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. Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ 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 Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
External links
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