neo-Inositol
Watchedfieldschanged
Verifiedrevid449559186
Iupacnameneo-Inositol[1]
Systematicname(1R,2R,3s,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol
Othernames(1s,2R,3R,4s,5S,6S)-cyclohexane-1,2,3,4,5,6-hexol; 1,2,3/4,5,6-cyclohexanehexol[2]

The chemical compound neo-inositol is one of the nine stereoisomers cyclohexane-1,2,3,4,5,6-hexol, the "inositols". Its formula is C6H12O6; the six carbon atoms form a ring, each of them is bonded to a hydrogen atom and a 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, specifically a sugar alcohol (to distinguish it from the more familiar ketose and aldose sugars, like 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 system with group P\bar 1. The cell parameters are a = 479.9 pm, b = 652.0 pm, c = 650.5 pm, α = 70.61°, β = 69.41°, γ = 73.66°, Z = 1, with molecular symmetry \bar 1. The cell volume is 0.176 nm3. The ring has the chair conformation with puckering parameter Q = 60.9 pm.[4]

Synthesis

neo-Inositol can be obtained from para-benzoquinone via conduritol intermediates.[5]

Natural occurrence and biological roles

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

See also

References

  1. ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1415. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. ^ "Neo-Inositol". Retrieved 9 October 2012.
  3. ^ Michell, R. H. (February 2008). "Inositol Derivatives: Evolution and Functions". Nature Reviews Molecular Cell Biology. 9 (2): 151–61. doi:10.1038/nrm2334. PMID 18216771
  4. ^ Younghee Yeon (2001): "The crystal and molecular structures of neo-inositol and two forms of scyllo-inositol". Korean Journal of Crystallography, volume 12, issue 3, pages 150-156.
  5. ^ 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
  6. ^ 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