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neo-Inositol

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*neo*-Inositol
Names

IUPAC name neo-Inositol^[2]
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]
Identifiers
CAS Number	488-54-0^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:25492^Y
ChemSpider	10199749^Y
UNII	8LQ63P85IC^Y
InChI InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4-,5-,6-^Y Key: CDAISMWEOUEBRE-DCLYFUHFSA-N^Y
SMILES O[C@H]1[C@@H](O)[C@H](O)[C@H](O)[C@H](O)[C@H]1O
Properties
Chemical formula	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	Irritating to eyes, respiratory system and skin.^[7]
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Chemical compound

Thechemical compoundneo-inositol is one of the ninestereoisomers cyclohexane-1,2,3,4,5,6-hexol, the "inositols". Itsformula isC₆H₁₂O₆; the sixcarbon atoms form a ring, each of them is bonded to ahydrogen atom and ahydroxyl 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 acarbohydrate, specifically asugar alcohol (to distinguish it from the more familiarketose andaldose sugars, likeglucose). It occurs in nature, but only in small amounts; usually much smaller than those ofmyo-inositol, the most important stereoisomer.^[8]

Chemical and physical properties

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Crystal structure

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neo-inositol crystallizes in thetriclinic system withgroup $P{\bar {1}}$ . The cell parameters area = 479.9pm,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 0.176nm³. The ring has thechair conformation with puckering parameterQ = 60.9 pm.^[4]

Synthesis

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neo-Inositol can be obtained frompara-benzoquinone viaconduritol intermediates.^[9]

Natural occurrence and biological roles

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Small amounts ofneo-inositol can be deteceted in human urine.^[10]

References

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^"Neo-Inositol". Retrieved9 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 atsynthose.com. Accessed on 2024-07-02.
^^a ^bYounghee Yeon (2001): "The crystal and molecular structures ofneo-inositol and two forms ofscyllo-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 589-600doi: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.doi:10.1063/1.1806792.PMID 15538878.
^"Material Safety Data Sheet". Sigma-Aldrich. Retrieved9 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 ofmyo-,neo-,L-chiro,D-chiro,allo-,scyllo-, andepi-inositol systems via conduritols prepared fromp-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