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.
Even simple cyclitols can be complicated from the perspective of stereochemistry. For example, cyclohexanetriol exists in three isomers. Furthermore, nine stereoisomers are possible for 1,2,3,4,5,6-cyclohexanehexol, 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
Substituted
- Bornesitol; -6-methoxycyclohexane-1,2,3,4,5-pentol; D--O-methyl-myo-inositol
- Pinitol; -6-methoxycyclohexane-1,2,3,4,5-pentol; 3-O-methyl-D-chiro-inositol
- Ononitol; -6-methoxycyclohexane-1,2,3,4,5-pentaol; 4-O-methyl-myo-inositol
- Pinpollitol; -3,6-dimethoxycyclohexane-1,2,4,5-tetraol; di-O-methyl--chiro-inositol
- Quebrachitol; -6-methoxycyclohexane-1,2,3,4,5-pentol; 2-0-methyl-chiro-inositol
- Quinic acid; -1,3,4,5-tetrahydroxycyclohexanecarboxylic acid
- Shikimic acid; -3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
- Valienol; -5-cyclohex-5-ene-1,2,3,4-tetrol
- Viscumitol -5,6-dimethoxycyclohexane-1,2,3,4-tetraol; 1,2-di-O-methyl-muco-inositol
Glycosides
- Ciceritol, a pinitol digalactoside
Phosphates
- Phytic acid; -cyclohexane-1,2,3,4,5,6-hexayl hexakis; inositol hexakisphosphate
Other cyclitols
- 1,2,3,4-Cyclohexanetetrol
- 1,2,3,4,5-Cyclopentanepentol
Applications