Lotaustralin
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| Names | |
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| IUPAC name
(2R)-2-(β-D-Glucopyranosyloxy)-2-methylbutanenitrile
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| Systematic IUPAC name
(2R)-2-Methyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanenitrile | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChemCID
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| UNII | |
CompTox Dashboard(EPA)
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| Properties | |
| C11H19NO6 | |
| Molar mass | 261.27 g/mol |
| Appearance | colorless needles |
| Density | 1.36 g·cm−3 |
| Melting point | 139 °C (282 °F; 412 K)[1] |
| good, also good inEthyl acetate[1] | |
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).
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Lotaustralinis acyanogenicglucosidefound in small amounts inFabaceaeaustral trefoil(Lotus australis),[1]cassava(Manihot esculenta),lima bean(Phaseolus lunatus),[2]roseroot(Rhodiola rosea)[3]andwhite clover(Trifolium repens),[4]among other plants. Lotaustralin is theglucosideofmethyl ethyl ketonecyanohydrinand is structurally related tolinamarin,the acetone cyanohydrin glucoside also found in these plants. Both lotaustralin and linamarin may be hydrolyzed by theenzymelinamaraseto formglucoseand a precursor to the toxic compoundhydrogen cyanide.
References
[edit]- ^abcShmuel Yannai:Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients.CRC Press, 2003,ISBN978-1-58488-416-3,p. 688
- ^Frehner M, Scalet M,Conn EE(1990)."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)".Plant Physiol.94(1): 28–34.doi:10.1104/pp.94.1.28.PMC1077184.PMID16667698.
- ^Akgul Y, Ferreira D, Abourashed E, Khan I (2004). "Lotaustralin from Rhodiola rosea roots".Fitoterapia.75(6): 612–4.doi:10.1016/j.fitote.2004.06.002.PMID15351122.
- ^"Notes on poisoning: Trifolium repens".Canadian Poisonous Plants Information System. May 30, 2006. Archived fromthe originalon June 10, 2011.Retrieved2007-02-11.