Neo-Inositol: Difference between revisions

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	{{DISPLAYTITLE:''neo''-Inositol}}		{{DISPLAYTITLE:''neo''-Inositol}}
	{{Chembox		{{Chembox
			\| Watchedfields = changed
	\| verifiedrevid = ~~444022556~~		\| verifiedrevid = 449559186
	\| ImageFile = Neo-inositol.svg		\| ImageFile = Neo-inositol.svg
	\| ImageSize =		\| ImageSize =
	\| Name = ''neo''-Inositol		\| Name = ''neo''-Inositol
			\| IUPACName = ''neo''-Inositol<ref>{{cite book \|author=] \|date=2014 \|title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 \|publisher=] \|pages=1415 \|doi=10.1039/9781849733069 \|isbn=978-0-85404-182-4}}</ref>
	\| IUPACName =
			\| SystematicName = (1''R'',2''R'',3''s'',4''S'',5''S'',6''s'')-cyclohexane-1,2,3,4,5,6-hexol
	\| OtherNames =
			\| OtherNames = (1s,2R,3R,4s,5S,6S)-cyclohexane-1,2,3,4,5,6-hexol;
⚫	\| Section1 = {{Chembox Identifiers
			1,2,3/4,5,6-cyclohexanehexol<ref name=chebi2012/>
	\| CASNo =
		⚫	\|Section1={{Chembox Identifiers
	\| PubChem =		\| PubChem =
			\| CASNo_Ref = {{cascite\|correct\|??}}
	\| CASNo = 488-54-0
	\| ~~PubChem~~ =		\| CASNo = 488-54-0
	\| ~~ChemSpiderID_Ref~~ = {{~~chemspidercite~~\|correct\|~~chemspider~~}}		\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| UNII = 8LQ63P85IC
			\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 10199749		\| ChemSpiderID = 10199749
	\| ChEBI_Ref = {{ebicite\|correct\|EBI}}		\| ChEBI_Ref = {{ebicite\|correct\|EBI}}
	\| ChEBI = 25492		\| ChEBI = 25492
	\| SMILES = O1(O)(O)(O)(O)1O		\| SMILES = O1(O)(O)(O)(O)1O
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| 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-		\| 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_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = CDAISMWEOUEBRE-DCLYFUHFSA-N		\| StdInChIKey = CDAISMWEOUEBRE-DCLYFUHFSA-N
	}}		}}
	\| Section2 = {{Chembox Properties		\|Section2={{Chembox Properties
	\| C=6\|H=12\|O=6		\| C=6 \| H=12 \| O=6
	\| Appearance =		\| Appearance = white crystalline solid <ref name=synthose/>
			\| Density = 1.697 g/ml (from X-ray structure)<ref name=yeon2001/>
	\| Density =
	\| ~~MeltingPt~~ =		\| MeltingPtK = 588
			\| MeltingPt_ref = <ref name=simp2006/><ref name=watt/>
	\| BoilingPt =		\| BoilingPt =
	\| Solubility = }}		\| Solubility =
			}}
	\| Section3 = {{Chembox Hazards		\|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>
	\| MainHazards =
	\| FlashPt =		\| FlashPt =
	\| ~~Autoignition~~ = }}		\| AutoignitionPt =
			}}
	}}		}}

			The ] '''''neo''-inositol''' is one of the nine ]s ], the "]s". Its ] is {{chem2\|C6H12O6}}; the six ] atoms form a ring, each of them is bonded to a ] atom and a ] group (–OH). If the ring is assumed horizontal, three consecutive hydroxyls lie above the respective hydrogens, and the other three lie below them.
	'''''neo''-Inositol''' is one of the ]s of ].

			Like the other stereoisomers, ''neo''-inositol is considered a ], specifically a ] (to distinguish it from the more familiar ] and ] sugars, like ]). 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 ] system with ] <math>P\bar 1</math>. The cell parameters are ''a'' = 479.9 ], ''b'' = 652.0 pm, ''c'' = 650.5 pm, α = 70.61], β = 69.41°, γ = 73.66°, ''Z'' = 1, with molecular symmetry <math>\bar 1</math>. The cell volume is 0.176 ]<sup>3</sup>. The ring has the ] with puckering parameter ''Q'' = 60.9 pm.<ref name=yeon2001/>

			==Synthesis==

			''neo''-Inositol can be obtained from ] via ] intermediates.<ref name=pode2003/>

			==Natural occurrence and biological roles==

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

	==See also==		==See also==
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	*]		*]

			==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>
⚫	{{DEFAULTSORT:Inositol, muco-}}

			<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): "". ''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): "". Product catalog page at . 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-}}
	]		]

Latest revision as of 07:49, 20 August 2024

*neo*-Inositol
Names

IUPAC name neo-Inositol
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
Identifiers
CAS Number	488-54-0
3D model (JSmol)	Interactive image
ChEBI	CHEBI:25492
ChemSpider	10199749
UNII	8LQ63P85IC
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-Key: CDAISMWEOUEBRE-DCLYFUHFSA-N
SMILES O1(O)(O)(O)(O)1O
Properties
Chemical formula	C₆H₁₂O₆
Molar mass	180.156 g·mol
Appearance	white crystalline solid
Density	1.697 g/ml (from X-ray structure)
Melting point	315 °C; 599 °F; 588 K
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Irritating to eyes, respiratory system and skin.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

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.

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 nm. 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

"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): "". Product catalog page at synthose.com. Accessed on 2024-07-02.
^ 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. 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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