Neo-Inositol

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neo-Inositol
Neo-inositol.svg
Names
IUPAC name
neo-Inositol [1]
Systematic IUPAC name
(1R,2R,3s,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol
Other names
(1s,2R,3R,4s,5S,6S)-cyclohexane-1,2,3,4,5,6-hexol; 1,2,3/4,5,6-cyclohexanehexol [2]
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4-,5-,6- Yes check.svgY
    Key: CDAISMWEOUEBRE-DCLYFUHFSA-N Yes check.svgY
  • O[C@H]1[C@@H](O)[C@H](O)[C@H](O)[C@H](O)[C@H]1O
Properties
C6H12O6
Molar mass 180.156 g·mol−1
Appearancewhite crystalline solid [3]
Density 1.697 g/ml (from X-ray structure) [4]
Melting point 315 °C; 599 °F; 588 K [5] [6]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Irritating to eyes, respiratory system and skin. [7]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.

Contents

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. [8]

Chemical and physical properties

Crystal structure

neo-inositol crystallizes in the triclinic system with group . 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 . The cell volume is 0.176 nm 3. 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. [9]

Natural occurrence and biological roles

Small amounts of neo-inositol can be deteceted in human urine. [10]

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. ↑ Synthose Inc. (2024): "". Product catalog page at synthose.com. Accessed on 2024-07-02.
  4. 1 2 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. ↑ Alexandra Simperler, Stephen W. Watt, P. Arnaud Bonnet, William Jones, W. D. Samuel Motherwell (2006): "Correlation of melting points of inositols with hydrogen bonding patterns". CrystEngComm, volume 8, pages 589-600 doi : 10.1039/B606107A
  6. ↑ Watt, S. W.; Chisholm, J. A.; Jones, W.; Motherwell, S. (2004). "A Molecular Dynamics Simulation of the Melting Points and Glass Transition Temperatures of Myo- and Neo-Inositol". Journal of Chemical Physics. 121 (19): 9565–9573. Bibcode:2004JChPh.121.9565W. doi:10.1063/1.1806792. PMID   15538878.
  7. ↑ "Material Safety Data Sheet". Sigma-Aldrich. Retrieved 9 October 2012.
  8. ↑ Michell, R. H. (February 2008). "Inositol Derivatives: Evolution and Functions" (PDF). Nature Reviews Molecular Cell Biology. 9 (2): 151–61. doi:10.1038/nrm2334. PMID   18216771.
  9. ↑ 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
  10. ↑ 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


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