Neo-Inositol
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.
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| Names | |
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| IUPAC name
neo-Inositol[2]
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| 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[1]
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| UNII | |
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| Properties | |
| C6H12O6 | |
| Molar mass | 180.156 g·mol−1 |
| Appearance | white 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
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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.
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
[edit]Crystal structure
[edit]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 nm3. The ring has the chair conformation with puckering parameter Q = 60.9 pm.[4]
Synthesis
[edit]neo-Inositol can be obtained from para-benzoquinone via conduritol intermediates.[9]
Natural occurrence and biological roles
[edit]Small amounts of neo-inositol can be deteceted in human urine.[10]
See also
[edit]- allo-Inositol
- cis-Inositol
- D-chiro-Inositol
- L-chiro-Inositol
- epi-Inositol
- muco-Inositol
- scyllo-Inositol
References
[edit]- ^ "Neo-Inositol". Retrieved 9 October 2012.
- ^ 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.
- ^ Synthose Inc. (2024): "[1]". Product catalog page at synthose.com. Accessed on 2024-07-02.
- ^ a b 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.
- ^ 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
- ^ 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.
- ^ "Material Safety Data Sheet". Sigma-Aldrich. Retrieved 9 October 2012.
- ^ 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.
- ^ 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
- ^ 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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