# Neo-Inositol

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The [chemical compound](/source/Chemical_compound) ***neo*-inositol** is one of the nine [stereoisomers](/source/Stereoisomer) [cyclohexane-1,2,3,4,5,6-hexol](/source/Cyclohexane-1,2,3,4,5,6-hexol), the "[inositols](/source/Inositol)". Its [formula](/source/Elemental_formula) is C6H12O6; the six [carbon](/source/Carbon) atoms form a ring, each of them is bonded to a [hydrogen](/source/Hydrogen) atom and a [hydroxyl](/source/Hydroxyl) group (–OH). If the ring is assumed horizontal, three consecutive hydroxyls lie above the respective hydrogens, and the other three lie below them.

Like the other stereoisomers, *neo*-inositol is considered a [carbohydrate](/source/Carbohydrate), specifically a [sugar alcohol](/source/Sugar_alcohol) (to distinguish it from the more familiar [ketose](/source/Ketose) and [aldose](/source/Aldose) sugars, like [glucose](/source/Glucose)). It occurs in nature, but only in small amounts; usually much smaller than those of *myo*-inositol, the most important stereoisomer.[3]

## Chemical and physical properties

### Crystal structure

*neo*-inositol crystallizes in the [triclinic](/source/Triclinic) system with [group](/source/Crystallographic_group) P\bar 1. The cell parameters are *a* = 479.9 [pm](/source/Picometre), *b* = 652.0 pm, *c* = 650.5 pm, α = 70.61[°](/source/Degree_(angle)), β = 69.41°, γ = 73.66°, *Z* = 1, with molecular symmetry \bar 1. The cell volume is 0.176 [nm](/source/Nanometre)3. The ring has the [chair conformation](/source/Cyclohexane_conformation) with puckering parameter *Q* = 60.9 pm.[4]

## Synthesis

*neo*-Inositol can be obtained from [*para*-benzoquinone](/source/P-benzoquinone) via [conduritol](/source/Conduritol) intermediates.[5]

## Natural occurrence and biological roles

Small amounts of *neo*-inositol can be deteceted in human urine.[6]

## See also

- [*allo*-Inositol](/source/Allo-Inositol)
- [*cis*-Inositol](/source/Cis-Inositol)
- [D-*chiro*-Inositol](/source/D-chiro-Inositol)
- [L-*chiro*-Inositol](/source/L-chiro-Inositol)
- [*epi*-Inositol](/source/Epi-Inositol)
- [*muco*-Inositol](/source/Muco-Inositol)
- [*scyllo*-Inositol](/source/Scyllo-Inositol)

## References

1. [International Union of Pure and Applied Chemistry](/source/International_Union_of_Pure_and_Applied_Chemistry) (2014). *Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013*. [The Royal Society of Chemistry](/source/Royal_Society_of_Chemistry). p. 1415. [doi:10.1039/9781849733069](https://doi.org/10.1039/9781849733069). ISBN 978-0-85404-182-4.

1. ["Neo-Inositol"](http://www.ebi.ac.uk/chebi/searchId.do;jsessionid=B128111F38B12846027AAFB90CCC28A6?chebiId=25492). Retrieved 9 October 2012.

1. Michell, R. H. (February 2008). ["Inositol Derivatives: Evolution and Functions"](http://xa.yimg.com/kq/groups/15186538/1872049761/name/panthini.pdf). *Nature Reviews Molecular Cell Biology*. **9** (2): 151–61. [doi:10.1038/nrm2334](https://doi.org/10.1038/nrm2334). [PMID 18216771](https://pubmed.ncbi.nlm.nih.gov/18216771)

1. Younghee Yeon (2001): "[The crystal and molecular structures of *neo*-inositol and two forms of *scyllo*-inositol](https://koreascience.kr/article/JAKO200111920935778.pdf)". *Korean Journal of Crystallography*, volume 12, issue 3, pages 150-156.

1. Michael Podeschwa, Oliver Plettenburg, Jochen vom Brocke, Oliver Block, Stephan Adelt, Hans-Josef Altenbach (2003): "Stereoselective synthesis of *myo*-, *neo*-, L-*chiro*, D-*chiro*, *allo*-, *scyllo*-, and *epi*-inositol systems via conduritols prepared from *p*-benzoquinone". *European Journal of Organic Chemistry*, volume 2003, issue 10, pages 1958-1972. [doi:10.1002/ejoc.200200572](https://doi.org/10.1002/ejoc.200200572)

1. Irina Monnard, Thierry Bénet, Rosemarie Jenni, Sean Austin, Irma Silva-Zolezzi, Jean-Philippe Godin (2020): "Plasma and urinary inositol isomer profiles measured by UHPLC-MS/MS reveal differences in scyllo-inositol levels between non-pregnant and pregnant women". *Analytical and Bioanalytical Chemistry*, volume 412, pages 7871–7880. [doi:10.1007/s00216-020-02919-8](https://doi.org/10.1007/s00216-020-02919-8)

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Adapted from the Wikipedia article [Neo-Inositol](https://en.wikipedia.org/wiki/Neo-Inositol) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Neo-Inositol?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.