neo-Inositol

*neo*-Inositol
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Template:Longitem	Template:Chembox Elements/molecular formula
Molar mass	Template:Chem molar mass
Appearance	white crystalline solid
Density	1.697 g/ml (from X-ray structure)
Melting point	Template:Chembox CalcTemperatures

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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 Template:Chem2; 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.^[6]

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.^[7]

Natural occurrence and biological roles

Small amounts of neo-inositol can be deteceted in human urine.^[8]

References

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↑ 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.
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↑ 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. Script error: No such module "CS1 identifiers".
↑ 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. Script error: No such module "CS1 identifiers".

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[chebi2012-1] Script error: No such module "citation/CS1".

[2] Script error: No such module "citation/CS1".

[synthose-3] Synthose Inc. (2024): "[1]". Product catalog page at synthose.com. Accessed on 2024-07-02.

[yeon2001-4] 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] Script error: No such module "citation/CS1".

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[pode2003-7] 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. Script error: No such module "CS1 identifiers".

[monn2020-8] 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. Script error: No such module "CS1 identifiers".

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neo-Inositol

Contents

Chemical and physical properties

Crystal structure

Synthesis

Natural occurrence and biological roles

See also

References

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neo-Inositol

Chemical and physical properties

Crystal structure

Synthesis

Natural occurrence and biological roles

See also

References

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