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Cyclitol

In organic chemistry, a cyclitol is a cycloalkane containing at least three hydroxyl, each attached to a different ring carbon atom. Most commonly, cyclitol refers to cyclic sugar alcohol. 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. Some cyclitols are parts of hydrolysable tannins.

Naturally occurring cyclitols
UnsubstitutedConduritol, 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 SubstitutedBornesitol; (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 GlycosidesCiceritol, a pinitol digalactoside PhosphatesPhytic acid; (1R,2S,3r,4R,5S,6s)-cyclohexane-1,2,3,4,5,6-hexayl hexakis[dihydrogen(phosphate)]; inositol hexakisphosphate Other cyclitols1,2,3,4-Cyclohexanetetrol1,2,3,4,5-Cyclopentanepentol ==Applications==
Applications
Aside from their utility to plants, cyclitols are useful as precursors to synthetic materials. ==Analysis methods==
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. ==Further reading==
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