Neo-Inositol: Difference between revisions

| Watchedfields = changed

| verifiedrevid = 449559186

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

| SystematicName = (1''R'',2''R'',3''s'',4''S'',5''S'',6''s'')-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<ref name=chebi2012/>

|Section1={{Chembox Identifiers

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

| CASNo = 488-54-0

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

| UNII = 8LQ63P85IC

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

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

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

}}

|Section2={{Chembox Properties

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

| Appearance = white crystalline solid <ref name=synthose/>

| Density = 1.697 g/ml (from X-ray structure)<ref name=yeon2001/>

| MeltingPtK = 588

| MeltingPt_ref = <ref name=simp2006/><ref name=watt/>

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards = Irritating to eyes, respiratory system and skin.<ref>{{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}}</ref>

| AutoignitionPt =

}}

The [[chemical compound]] '''''neo''-inositol''' is one of the nine [[stereoisomer]]s [[cyclohexane-1,2,3,4,5,6-hexol]], the "[[inositol]]s". Its [[elemental formula|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.<ref name=mich2008/>

==Chemical and physical properties==

===Crystal structure===

''neo''-inositol crystallizes in the [[triclinic]] system with [[crystallographic group|group]] <math>P\bar 1</math>. The cell parameters are ''a'' = 479.9 [[picometre|pm]], ''b'' = 652.0 pm, ''c'' = 650.5 pm, α = 70.61[[degree (angle)|°]], β = 69.41°, γ = 73.66°, ''Z'' = 1, with molecular symmetry <math>\bar 1</math>. The cell volume is 0.176 [[nanometre|nm]]³. The ring has the [[cyclohexane conformation|chair conformation]] with puckering parameter ''Q'' = 60.9 pm.<ref name=yeon2001/>

==Synthesis==

''neo''-Inositol can be obtained from [[p-benzoquinone|''para''-benzoquinone]] via [[conduritol]] intermediates.<ref name=pode2003/>

==Natural occurrence and biological roles==

Small amounts of ''neo''-inositol can be deteceted in human urine.<ref name=monn2020/>

==References==

<references>

<ref name=chebi2012>{{cite web|title=Neo-Inositol|url=http://www.ebi.ac.uk/chebi/searchId.do;jsessionid=B128111F38B12846027AAFB90CCC28A6?chebiId=25492|accessdate=9 October 2012}}</ref>

<ref name=mich2008>{{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}}</ref>

<ref name=pode2003>Michael Podeschwa, Oliver Plettenburg, Jochen vom Brocke, Oliver Block, Stephan Adelt, Hans-Josef Altenbach (2003): "Stereoselective synthesis of ''myo''-, ''neo''-, <small>L</small>-''chiro'', <small>D</small>-''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}}</ref>

<ref name=yeon2001>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.</ref>

<ref name=watt>{{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}}</ref>

<ref name=simp2006>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}}</ref>

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

<ref name=monn2020>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}}</ref>

</references>

{{DEFAULTSORT:Inositol, muco-}}