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

Unsubstituted

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

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

Ciceritol, a pinitol digalactoside

Phosphates

Phytic acid; (1R,2S,3r,4R,5S,6s)-cyclohexane-1,2,3,4,5,6-hexayl hexakis[dihydrogen(phosphate)]; inositol hexakisphosphate

Other cyclitols

Applications

Aside from their utility to plants, cyclitols are useful as precursors to synthetic materials.^[6]

Analysis methods

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]

References

^ IUPAC, Compendium of Chemical Terminology, 5th ed. (the "Gold Book") (2025). Online version: (2006–) "Cyclitols". doi:10.1351/goldbook.C01493
^ Vovener de Verlands, Edmond; Hong, Zonglie; Nelson, Andrew S. (2025). "Sugar alcohols in plants: implications for enhancing tree seedlings drought tolerance and production strategies". BMC Plant Biology. 28 (1) 891. Bibcode:2025BMCPB..25..891E. doi:10.1186/s12870-025-06860-9. PMC 12239448. PMID 40634904.
^ Hoch, G.; Richter, A.; Körner, Ch. (2003). "Non-structural carbon compounds in temperate forest trees". Plant, Cell & Environment. 26 (7): 1067–1081. Bibcode:2003PCEnv..26.1067H. doi:10.1046/j.0016-8025.2003.01032.x.
^ 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. doi:10.1139/f69-282
^ 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. doi:10.1021/jo00249a039
^ Ferrier, Robert J.; Middleton, Sydney (1993). "The conversion of carbohydrate derivatives into functionalized cyclohexanes and cyclopentanes". Chemical Reviews. 93 (8): 2779–2831. doi:10.1021/cr00024a008.
^ 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 doi:10.1002/hlca.19550380122

External links

List of cyclitol molecules on chemicalland21.com

[1] IUPAC, Compendium of Chemical Terminology, 5th ed. (the "Gold Book") (2025). Online version: (2006–) "Cyclitols". doi:10.1351/goldbook.C01493

[Vovener_de_Verlands_et_al_2025-2] Vovener de Verlands, Edmond; Hong, Zonglie; Nelson, Andrew S. (2025). "Sugar alcohols in plants: implications for enhancing tree seedlings drought tolerance and production strategies". BMC Plant Biology. 28 (1) 891. Bibcode:2025BMCPB..25..891E. doi:10.1186/s12870-025-06860-9. PMC 12239448. PMID 40634904.

[3] Hoch, G.; Richter, A.; Körner, Ch. (2003). "Non-structural carbon compounds in temperate forest trees". Plant, Cell & Environment. 26 (7): 1067–1081. Bibcode:2003PCEnv..26.1067H. doi:10.1046/j.0016-8025.2003.01032.x.

[craig1969-4] 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. doi:10.1139/f69-282

[akbu1988-5] 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. doi:10.1021/jo00249a039

[6] Ferrier, Robert J.; Middleton, Sydney (1993). "The conversion of carbohydrate derivatives into functionalized cyclohexanes and cyclopentanes". Chemical Reviews. 93 (8): 2779–2831. doi:10.1021/cr00024a008.

[post1955a-7] 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 doi:10.1002/hlca.19550380122

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