Neo-Inositol

{{Chembox

| Watchedfields = changed

| verifiedrevid = 449559186

| ImageFile = Neo-inositol.svg

| ImageSize =

| Name = neo-Inositol

| IUPACName = neo-Inositol{{cite book |author=International Union of Pure and Applied Chemistry |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=The Royal Society of Chemistry |pages=1415 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}

| 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

|Section1={{Chembox Identifiers

| PubChem =

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 488-54-0

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 8LQ63P85IC

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 10199749

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 25492

| SMILES = O[C@H]1[C@@H](O)[C@H](O)[C@H](O)[C@H](O)[C@H]1O

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4-,5-,6-

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = CDAISMWEOUEBRE-DCLYFUHFSA-N

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|Section2={{Chembox Properties

| C=6 | H=12 | O=6

| Appearance = white crystalline solid

| Density = 1.697 g/ml (from X-ray structure)

| MeltingPtK = 588

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| BoilingPt =

| Solubility =

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|Section3={{Chembox Hazards

| MainHazards = Irritating to eyes, respiratory system and skin.{{cite web|title=Material Safety Data Sheet|url=http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=US&language=en&productNumber=516163&brand=ALDRICH&PageToGoToURL=http%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Faldrich%2F516163%3Flang%3Den|publisher=Sigma-Aldrich|accessdate=9 October 2012}}

| FlashPt =

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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 {{chem2|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.

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.

Synthesis

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

Natural occurrence and biological roles

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

References

{{cite web|title=Neo-Inositol|url=http://www.ebi.ac.uk/chebi/searchId.do;jsessionid=B128111F38B12846027AAFB90CCC28A6?chebiId=25492|accessdate=9 October 2012}}

{{cite journal|last=Michell|first=R. H.|title=Inositol Derivatives: Evolution and Functions|journal=Nature Reviews Molecular Cell Biology|date=February 2008|volume=9|issue=2|doi=10.1038/nrm2334 |url=http://xa.yimg.com/kq/groups/15186538/1872049761/name/panthini.pdf|pmid=18216771|pages=151–61}}

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}}

Younghee Yeon (2001): "[https://koreascience.kr/article/JAKO200111920935778.pdf 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.

{{cite journal|last=Watt|first=S. W.|author2=Chisholm, J. A. |author3=Jones, W. |author4= Motherwell, S. |title=A Molecular Dynamics Simulation of the Melting Points and Glass Transition Temperatures of Myo- and Neo-Inositol|journal=Journal of Chemical Physics|year=2004|volume=121|issue=19|pages=9565–9573|doi=10.1063/1.1806792|pmid=15538878|bibcode=2004JChPh.121.9565W }}

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}}

Synthose Inc. (2024): "[https://synthose.com/products/NI530 ]". Product catalog page at [https://synthose.com synthose.com]. Accessed on 2024-07-02.

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}}

Category:Inositol