# Cyclitol

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Class of chemical compounds

[inositol](/source/Inositol) is a common cyclitol.

In [organic chemistry](/source/Organic_chemistry), a **cyclitol** is a [cycloalkane](/source/Cycloalkane) containing at least three [hydroxyl](/source/Hydroxyl), each attached to a different ring carbon atom.[1] Most commonly, cyclitol refers to cyclic [sugar alcohol](/source/Sugar_alcohol).[2] Cyclitols and their derivatives are some of the [compatible solutes](/source/Osmoprotectant) 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](/source/Quinic_acid) or [shikimic acid](/source/Shikimic_acid)) are parts of [hydrolysable tannins](/source/Hydrolysable_tannin).

Even simple cyclitols can be complicated by different [isomeric](/source/Isomer) possibilies. For example, there are three different [constitutional isomers](/source/Constitutional_isomer) of cyclohexanetriol: 1,2,3-, 1,2,4-, and 1,3,5-. And even though there is only one reasonably stable constitutional isomer of cyclohexanehexol ([inositol](/source/Inositol)), there are nine [stereoisomers](/source/Stereoisomer) possible.

## Naturally occurring cyclitols

### Unsubstituted

- [Conduritol](/source/Conduritol), or cyclohex-5-ene-1,2,3,4-tetrol; two out of ten possible isomers.

- [Inositol](/source/Inositol), or cyclohexane-1,2,3,4,5,6-hexol; four out of nine possible isomers.

- [Cyclohexanetetrol](/source/Cyclohexanetetrol)[4]

### Substituted

- [Bornesitol](/source/Bornesitol); (1R,2R,3S,4S,5R,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol; D-(−)-O-methyl-*myo*-inositol

- [Pinitol](/source/Pinitol); (1S,2S,4S,5R)-6-methoxycyclohexane-1,2,3,4,5-pentol; 3-O-methyl-D-*chiro*-inositol

- [Ononitol](/source/Ononitol); (1R,2S,3S,4S,5S,6S)-6-methoxycyclohexane-1,2,3,4,5-pentaol; 4-O-methyl-*myo*-inositol

- [Pinpollitol](/source/Pinpollitol); (1R,2R,3R,4S,5R,6S)-3,6-dimethoxycyclohexane-1,2,4,5-tetraol; di-O-methyl-(+)-*chiro*-inositol

- [Quebrachitol](/source/Quebrachitol); (1R,2S,4S,5R)-6-methoxycyclohexane-1,2,3,4,5-pentol; 2-0-methyl-*chiro*-inositol

- [Quinic acid](/source/Quinic_acid); (1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid

- [Shikimic acid](/source/Shikimic_acid); (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid

- [Valienol](/source/Valienol); (1S,2S,3S,4R)-5-(Hydroxymethyl)cyclohex-5-ene-1,2,3,4-tetrol

- [Viscumitol](/source/Viscumitol) (1R,2S,3R,4S,5R,6S)-5,6-dimethoxycyclohexane-1,2,3,4-tetraol; 1,2-di-O-methyl-*muco*-inositol

### Glycosides

- [Ciceritol](/source/Ciceritol), a pinitol digalactoside

### Phosphates

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

### Other cyclitols

- [1,2,3,4-Cyclohexanetetrol](/source/1%2C2%2C3%2C4-Cyclohexanetetrol)[5]

- [1,2,3,4,5-Cyclopentanepentol](/source/1%2C2%2C3%2C4%2C5-Cyclopentanepentol)

## 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](/source/Paper_chromatography) using three methods of development: [Tollens' reagents](/source/Tollens'_reagent), the [Meillère reagent](https://en.wikipedia.org/w/index.php?title=Meill%C3%A8re_reagent&action=edit&redlink=1) (based on the [Scherer-Gallois reaction](https://en.wikipedia.org/w/index.php?title=Scherer-Gallois_reaction&action=edit&redlink=1)), and digestion by *[Acetobacter suboxydans](https://en.wikipedia.org/w/index.php?title=Acetobacter_suboxydans&action=edit&redlink=1)* followed by Tollens' reagent.[7]

## Further reading

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. [doi](/source/Doi_(identifier)):[10.1111/j.1432-1033.1968.tb00328.x](https://doi.org/10.1111%2Fj.1432-1033.1968.tb00328.x)

## See also

- [Aminocyclitol](/source/Aminocyclitol)

## References

1. **[^](#cite_ref-1)** [IUPAC](/source/International_Union_of_Pure_and_Applied_Chemistry), *[Compendium of Chemical Terminology](/source/IUPAC_books#Gold_Book)*, 5th ed. (the "Gold Book") (2025). Online version: (2006–) "[Cyclitols](https://goldbook.iupac.org/terms/view/C01493.html)". [doi](/source/Doi_(identifier)):[10.1351/goldbook.C01493](https://doi.org/10.1351%2Fgoldbook.C01493)

1. **[^](#cite_ref-Vovener_de_Verlands_et_al_2025_2-0)** Vovener de Verlands, Edmond; Hong, Zonglie; Nelson, Andrew S. (2025). ["Sugar alcohols in plants: implications for enhancing tree seedlings drought tolerance and production strategies"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12239448). *BMC Plant Biology*. **28** (1) 891. [Bibcode](/source/Bibcode_(identifier)):[2025BMCPB..25..891E](https://ui.adsabs.harvard.edu/abs/2025BMCPB..25..891E). [doi](/source/Doi_(identifier)):[10.1186/s12870-025-06860-9](https://doi.org/10.1186%2Fs12870-025-06860-9). [PMC](/source/PMC_(identifier)) [12239448](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12239448). [PMID](/source/PMID_(identifier)) [40634904](https://pubmed.ncbi.nlm.nih.gov/40634904).

1. **[^](#cite_ref-3)** Hoch, G.; Richter, A.; Körner, Ch. (2003). "Non-structural carbon compounds in temperate forest trees". *Plant, Cell & Environment*. **26** (7): 1067–1081. [Bibcode](/source/Bibcode_(identifier)):[2003PCEnv..26.1067H](https://ui.adsabs.harvard.edu/abs/2003PCEnv..26.1067H). [doi](/source/Doi_(identifier)):[10.1046/j.0016-8025.2003.01032.x](https://doi.org/10.1046%2Fj.0016-8025.2003.01032.x).

1. **[^](#cite_ref-craig1969_4-0)** 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](/source/Doi_(identifier)):[10.1139/f69-282](https://doi.org/10.1139%2Ff69-282)

1. **[^](#cite_ref-akbu1988_5-0)** 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](/source/Doi_(identifier)):[10.1021/jo00249a039](https://doi.org/10.1021%2Fjo00249a039)

1. **[^](#cite_ref-6)** Ferrier, Robert J.; Middleton, Sydney (1993). "The conversion of carbohydrate derivatives into functionalized cyclohexanes and cyclopentanes". *Chemical Reviews*. **93** (8): 2779–2831. [doi](/source/Doi_(identifier)):[10.1021/cr00024a008](https://doi.org/10.1021%2Fcr00024a008).

1. **[^](#cite_ref-post1955a_7-0)** 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](/source/Doi_(identifier)):[10.1002/hlca.19550380122](https://doi.org/10.1002%2Fhlca.19550380122)

## External links

Look up ***[cyclitol](https://en.wiktionary.org/wiki/cyclitol)*** in Wiktionary, the free dictionary.

Authority control databases: National Japan

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