Lotaustralin: Difference between revisions

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Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (
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{{chembox
{{chembox
| Verifiedfields = changed
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| verifiedrevid = 401620386
| Watchedfields = changed
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| ImageFile1 = Lotaustralin Structural Formulae V.1.svg
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| verifiedrevid = 424328298
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| ImageSize1 = 200px
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| ImageFile1 = Lotaustralin structure.svg
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| ImageSize1 =
| ImageFile2 = Lotaustralin 3D sticks.png
| ImageFile2 = Lotaustralin 3D sticks.png
| IUPACName = (2''R'')-2-(β-<small>D</small>-Glucopyranosyloxy)-2-methylbutanenitrile
| IUPACName =
(2''R'')-2-methyl-2-{[(2''S'',3''R'',4''S'',5''S'',6''R'')-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2''H''-pyran-2-yl]oxy}butanenitrile
| SystematicName = (2''R'')-2-Methyl-2-<nowiki/>{[(2''S'',3''R'',4''S'',5''S'',6''R'')-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanenitrile
| IUPACName_hidden=yes
| OtherNames =
| OtherNames =
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 534-67-8
| CASNo = 534-67-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = P588137A94
| PubChem = 441467
| PubChem = 441467
| SMILES = CC[C@](C)(C#N)O[C@H]1[C@@H]([C@H]([C@@H]<br>([C@H](O1)CO)O)O)O }}
| SMILES = CC[C@](C)(C#N)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
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| Section2 = {{Chembox Properties
| ChemSpiderID = 390193
| InChI = 1/C11H19NO6/c1-3-11(2,5-12)18-10-9(16)8(15)7(14)6(4-13)17-10/h6-10,13-16H,3-4H2,1-2H3/t6-,7-,8+,9-,10+,11-/m1/s1
| InChIKey = WEWBWVMTOYUPHH-QHAQEBJBBY
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C11H19NO6/c1-3-11(2,5-12)18-10-9(16)8(15)7(14)6(4-13)17-10/h6-10,13-16H,3-4H2,1-2H3/t6-,7-,8+,9-,10+,11-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = WEWBWVMTOYUPHH-QHAQEBJBSA-N}}
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|Section2={{Chembox Properties
| MolarMass = 261.27 g/mol
| MolarMass = 261.27 g/mol
| Appearance = colorless needles
| Appearance = colorless needles
| C = 11 | H = 19 | N = 1 | O = 6
| C=11 | H=19 | N=1 | O=6
| Density = 1.36&nbsp;g&middot;cm<sup>-3</sup>
| Density = 1.36&nbsp;g&middot;cm<sup>−3</sup>
| MeltingPtC = 139
| MeltingPt = 139 °C <ref name=dofc>Shmuel Yannai: ''Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients.'' CRC Press, 2003, ISBN 9781584884163, p. 688</ref>
| MeltingPt_ref = <ref name=dofc>Shmuel Yannai: ''Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients.'' CRC Press, 2003, {{ISBN|978-1-58488-416-3}}, p. 688</ref>
| Solubility =good, also good in [[Ethyl acetate]] <ref name=dofc/>
| Solubility =good, also good in [[Ethyl acetate]]<ref name=dofc/>
| BoilingPt = }}
| BoilingPt = }}
| Section3 = {{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards =
| MainHazards =
| FlashPt =
| FlashPt =
| Autoignition = }}
| AutoignitionPt =
}}
}}
}}


'''Lotaustralin''' is a [[cyanide|cyanogenic]] [[glucoside]] found in small amounts in [[Fabaceae]] [[Lotus australis|Austral Trefoil]] (''Lotus australis''),<ref name=dofc/> [[cassava]] (''Manihot esculenta''), [[lima bean]] (''Phaseolus lunatus''),<ref>{{cite journal |author= Frehner M, Scalet M, Conn EE |title=Pattern of the Cyanide-Potential in Developing Fruits : Implications for Plants Accumulating Cyanogenic Monoglucosides (Phaseolus lunatus) or Cyanogenic Diglucosides in Their Seeds (Linum usitatissimum, Prunus amygdalus) |journal=Plant Physiol |volume=94 |issue=1 |pages=28–34 |year=1990 |pmid= 16667698 |doi= 10.1104/pp.94.1.28 |pmc= 1077184}} {{PMC|1077184}}</ref> [[Rhodiola rosea|roseroot]] (''Rhodiola rosea'')<ref>{{cite journal |author=Akgul Y, Ferreira D, Abourashed E, Khan I |title=Lotaustralin from Rhodiola rosea roots |journal=Fitoterapia |volume=75 |issue=6 |pages=612–4 |year=2004 |pmid= 15351122 |doi=10.1016/j.fitote.2004.06.002}}</ref> and [[white clover]] (''Trifolium repens''),<ref>{{cite web| url = http://www.cbif.gc.ca/pls/pp/ppack.info?p_psn=258&p_type=all&p_sci=sci&p_x=pp | title = Notes on poisoning: Trifolium repens | accessdate = 2007-02-11 | date = May 30, 2006 | publisher = Canadian Poisonous Plants Information System}}</ref> among other plants. Lotaustralin is the [[glucoside]] of [[methyl ethyl ketone]] [[cyanohydrin]] and is structurally related to [[linamarin]], the acetone cyanohydrin glucoside also found in these plants. Both lotaustralin and linamarin may be hydrolyzed by the [[enzyme]] [[linamarase]] to form [[glucose]] and a precursor to the toxic compound [[hydrogen cyanide]].
'''Lotaustralin''' is a [[cyanide|cyanogenic]] [[glucoside]] found in small amounts in [[Fabaceae]] [[Lotus australis|austral trefoil]] (''Lotus australis''),<ref name=dofc/> [[cassava]] (''Manihot esculenta''), [[lima bean]] (''Phaseolus lunatus''),<ref>{{cite journal |vauthors=Frehner M, Scalet M, Conn EE |author-link3=Eric Conn |title=Pattern of the Cyanide-Potential in Developing Fruits : Implications for Plants Accumulating Cyanogenic Monoglucosides (Phaseolus lunatus) or Cyanogenic Diglucosides in Their Seeds (Linum usitatissimum, Prunus amygdalus) |journal=Plant Physiol |volume=94 |issue=1 |pages=28–34 |year=1990 |pmid= 16667698 |doi= 10.1104/pp.94.1.28 |pmc= 1077184}}</ref> [[Rhodiola rosea|roseroot]] (''Rhodiola rosea'')<ref>{{cite journal |vauthors=Akgul Y, Ferreira D, Abourashed E, Khan I |title=Lotaustralin from Rhodiola rosea roots |journal=Fitoterapia |volume=75 |issue=6 |pages=612–4 |year=2004 |pmid= 15351122 |doi=10.1016/j.fitote.2004.06.002}}</ref> and [[white clover]] (''Trifolium repens''),<ref>{{cite web | url = http://www.cbif.gc.ca/pls/pp/ppack.info?p_psn=258&p_type=all&p_sci=sci&p_x=pp | title = Notes on poisoning: Trifolium repens | access-date = 2007-02-11 | date = May 30, 2006 | publisher = Canadian Poisonous Plants Information System | url-status = dead | archive-url = https://web.archive.org/web/20110610071001/http://www.cbif.gc.ca/pls/pp/ppack.info?p_psn=258&p_type=all&p_sci=sci&p_x=pp | archive-date = June 10, 2011 }}</ref> among other plants. Lotaustralin is the [[glucoside]] of [[methyl ethyl ketone]] [[cyanohydrin]] and is structurally related to [[linamarin]], the acetone cyanohydrin glucoside also found in these plants. Both lotaustralin and linamarin may be hydrolyzed by the [[enzyme]] [[linamarase]] to form [[glucose]] and a precursor to the toxic compound [[hydrogen cyanide]].


==References==
== References ==
{{Reflist}}
{{Reflist}}


{{Glycosides}}
{{Glycosides}}


[[Category:Cyanogenic glycosides]]
[[Category:Glucosides]]
[[Category:Glucosides]]
[[Category:Plant toxins]]
[[Category:Plant toxins]]
[[Category:Nitriles]]




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