Cyclitol

Source: Wikipedia, the free encyclopedia.
The cyclitol 1,2,3,4-cyclohexanetetrol (n=6, x=4). There are actually 10 isomers with this same structure.

In

hydroxyl, each attached to a different ring carbon atom.[1]
The general formula for an unsubstituted cyclitol is C
nH
2n-x(OH)
x or C
nH
2nO
x where 3 ≤ x ≤ n.

The name is also used for compounds that can be viewed as result of substituting various functional groups for the hydrogen atoms in such a molecule, as well as similar molecules with one or more double bonds in the ring.[citation needed]

Cyclitols and their derivatives are some of the compatible solutes which are formed in a plant as a response to salt or water stress. Some cyclitols (e.g. quinic 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

IUPAC has provided a nomenclature for cyclitol stereoisomers.[2]

Naturally occurring cyclitols

Unsubstituted

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

Phosphates

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

Other cyclitols

Analysis methods

In 1955,

Tollens reagents, the Meillère reagent (based on the Scherer-Gallois reaction), and digestion by Acetobacter suboxydans followed by Tollens reagent.[5]

See also

References

  1. doi:10.1351/goldbook.C01493
  2. doi:10.1111/j.1432-1033.1968.tb00328.x
  3. doi:10.1139/f69-282
  4. doi:10.1021/jo00249a039
  5. doi:10.1002/hlca.19550380122

External links

Look up cyclitol in Wiktionary, the free dictionary.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Cyclitol&oldid=1143330457"