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{{DISPLAYTITLE:<small>L</small>-''chiro''-Inositol}} |
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{{DISPLAYTITLE:1<small>L</small>-''chiro''-Inositol}} |
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{{Chembox |
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{{Chembox |
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| Watchedfields = changed |
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| verifiedrevid = 443914126 |
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| verifiedrevid = 449558668 |
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| ImageFile = L-chiro-inositol.svg |
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| ImageFile = L-chiro-inositol.svg |
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| ImageSize = |
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| ImageSize = |
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| Name = <small>L</small>-''chiro''-Inositol |
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| Name = 1<small>L</small>-''chiro''-Inositol |
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| IUPACName = |
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| IUPACName = 1<small>L</small>-''chiro''-Inositol |
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| SystematicName = (1''R'',2''R'',3''R'',4''R'',5''S'',6''S'')-Cyclohexane-1,2,3,4,5,6-hexol |
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| OtherNames = |
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| OtherNames = (-)-1,2,4/3,5,6-inositol<br/>L-(−)-chiro-Inositol |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = 551-72-4 |
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| CASNo_Ref = {{cascite|correct|??}} |
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| PubChem = |
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| CASNo = 551-72-4 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 63GQX5QW03 |
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| PubChem = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10199754 |
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| ChemSpiderID = 10199754 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 27374 |
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| ChEBI = 27374 |
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| SMILES = O1(O)(O)(O)(O)1O |
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| SMILES = O1(O)(O)(O)(O)1O |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4-,5+,6+/m1/s1 |
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| StdInChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4-,5+,6+/m1/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = CDAISMWEOUEBRE-SHFUYGGZSA-N |
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| StdInChIKey = CDAISMWEOUEBRE-SHFUYGGZSA-N |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=6|H=12|O=6 |
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| C=6 | H=12 | O=6 |
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| Appearance = |
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| Appearance = |
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| Density = |
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| Density = |
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| MeltingPt = |
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| MeltingPt = 230 °C (decomposes) <ref name=merc2024/> |
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| BoilingPt = |
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| BoilingPt = |
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| Solubility = }} |
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| Solubility = 485 g/L <ref name=merc2024/> |
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| SpecRotation = 20/ −60°, c=1.3 in H2O <ref name=merc2024/> |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| Autoignition = }} |
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| AutoignitionPt = }} |
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The ] '''1<small>L</small>-''chiro''-inositol'''<ref name=bluebk/> (often called '''L-''chiro''-inositol''' or '''LCI''') is one of the nine ]s of ], with formula {{chem2|C6H12O6}}, the generic "]". Its molecule has a ring of six ] atoms, each bonded to a ] atom and a ] group (–OH). Imagining the ring is horizontal, the hydroxyls on carbons 1, 2, and 4, in clockwise order are above the respective hydrogens, while the other three are below them. |
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'''<small>L</small>-''chiro''-Inositol''' is one of the ]s of ]. |
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The compound occurs in the human body and other organisms, together with its ] (mirror image isomer) ] (DCI), but at a much lower concentration than the main isomer ]. |
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==Structure== |
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L-''chiro''-inositol crystallizes in the ] system, ] P2<sub>1</sub>, with cell dimensions ''a'' = 686.7 ], ''b'' = 913.3 pm, ''c'' = 621.7 pm (±0.004 pm) angle ''β'' = 106.59] (± 0.04°), molecular count ''Z'' = 2. The molecule has the expected ], with puckering parameters ''Q'' = 56.1 pm, ''θ'' = 4.4°, ''φ'' = 51.2°. The non-hydrogen molecular symmetry is close to C<sub>2</sub>. The C–C bond lengths range from 151.5 to 152.8 pm, and the C–O bond lengths from 141.8 to 143.6 pm. The C–C–C angles range from 109.7 to 113.1°, and the C–C–O angles from 106.5 to 112.0°.<ref name=jeff1987/> |
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==Laboratory synthesis== |
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L-''chiro''-inositol can be prepared from ''myo''-inositol.<ref name=bele2003/> It can be prepared also from ] by ] action on a derived ] intermediate;<ref name=pode2003/> or by controlled oxidation of ].<ref name=bram1998/><ref name=carl1993/> |
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Another viable method is decomposition of plant-sourced ], which can be obtained in good quantity from ] (NRS), the liquid remaining from coagulation of ] from '']''.<ref name=leec2023/> |
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==Natural occurrence== |
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L-''chiro''-inositol occurs, together with the D- isomer, in ] of animal tissues. Analysis of rat tissues shows predominance of DCI in fat, liver, brain and kidney, and approximately equal amounts of DCI and LCI in muscles. L-chiro-inositol is also found in plants and parasites as ], an ] of LCI — specifically, 2-O-methyl-L-''chiro''-inositol.<ref name=larn2000/> <ref name=leec2023/> |
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L-''chiro''-inositol can be extracted from dead leaf material from the seagrass '']'' that washes up as flotsam on Caribbean beaches. Yeld of 2.3–2.5% of dry weight has been reported.<ref name=nuis2008/> |
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Microbial action in soil incubated for 12 days at 70% moisture converted about 4% of the at converted about 4% of infused ''myo''-inositol to ''chiro''-inositol of unspecified (D or L) optical activity.<ref name=annu1977/> |
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==See also== |
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==See also== |
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==References== |
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{{DEFAULTSORT:Inositol, L-chiro-}} |
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<references> |
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<ref name=jeff1987>George A. Jeffrey, Younghee Yeon (1987): "The crystal structure of l-chiro-inositol". ''Carbohydrate Research'', volume 159, issue 2, pages 211-216. {{doi|10.1016/S0008-6215(00)90216-7}}</ref> |
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<ref name=bluebk>{{BlueBook2013|rec=104.2.1}}</ref> |
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<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> |
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{{alcohol-stub}} |
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<ref name=bele2003>M. Belén Cid, Francisco Alfonso, Manuel Martín-Lomas (2003): "L-''chiro''-inositol derivatives from ''myo''-inositol. Building blocks for inositol phosphoglycans". ''Synlett'', volume 2003, issue 9, pages 1370-1372. {{doi|10.1055/s-2003-40339}}</ref> |
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<ref name=bram1998>Larry E Brammer Jr., Tomas Hudlicky (1998): "Inositol synthesis: concise preparation of l-chiro-inositol and muco-inositol from a common intermediate". ''Tetrahedron: Asymmetry'', volume 9, issue 12, 19 june , pages 2011-2014 {{doi|10.1016/S0957-4166(98)00182-7}}</ref> |
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<ref name=leec2023>Christine Sue Chen Lee, Manroshan Singh, Chin-Hoe Teh, Dazylah Darji, Azhar Ahmad & Zairossani Mohd Nor (2023): "Modification of quebrachitol extracted from natural rubber serum (NRS) to L-''chiro''-inositol for pharmaceutical and nutraceutical applications". ''Journal of Rubber Research'', volume 26, pages 179–192 {{doi|10.1007/s42464-023-00218-2}}</ref> |
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<ref name=nuis2008>Gladys Nuissier a, Faïza Diaba b, Micheline Grignon-Dubois a (2008): "Bioactive agents from beach waste: ''Syringodium'' flotsam evaluation as a new source of L-''chiro''-inositol". ''Innovative Food Science & Emerging Technologies'', volume 9, issue 3, pages 396-400. {{doi|10.1016/j.ifset.2007.12.002}}</ref> |
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<ref name=annu1977>Michael F. L'Annunziata, Juan González Iturbe, Luis A. Olivares Orozco (1977) "Microbial epimerization of ''myo''-inositol to ''chiro''-inositol in soil". ''Soil Science Society of America Journal'', Division S-3 - ''Soil Microbiology and Biochemistry'', volume 41, issue 4, pages 733-736. {{doi|10.2136/sssaj1977.03615995004100040024x}}</ref> |
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<ref name=merc2024>Sigma-Aldrich (2024), "". Online catalog, accessed on 2024-06-31.</ref> |
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<ref name=larn2000>Joseph Larner (2000): "D-chiro-inositol – Its functional role in insulin action and its deficit in insulin resistance". ''Journal of Diabetes Research'', volume 3, pages 47-60. {{doi|10.1080/15604280212528}}</ref> |
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<ref name=carl1993>Howard A. J. Carless, K. Busia, O. Z. Oak (1993): "Microbial oxidation of benzene as a route to inositol stereoisomers and (±)-quebrachitol". ''Synlett'', volume 1993, issue 9, pages 672-674. {{doi|10.1055/s-1993-22567}}</ref> |
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</references> |
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{{DEFAULTSORT:Inositol, L-chiro-}} |
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