Lotaustralin

Lotaustralin
Names
IUPAC name
(2R)-2-(β-D-Glucopyranosyloxy)-2-methylbutanenitrile
Systematic IUPAC name
(2R)-2-Methyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanenitrile
Identifiers
CAS Number
  • 534-67-8 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 390193 ☒N
PubChem CID
  • 441467
UNII
  • P588137A94 checkY
CompTox Dashboard (EPA)
  • DTXSID30897501 Edit this at Wikidata
InChI
  • InChI=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 ☒N
    Key: WEWBWVMTOYUPHH-QHAQEBJBSA-N ☒N
  • 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
    Key: WEWBWVMTOYUPHH-QHAQEBJBBY
  • CC[C@](C)(C#N)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
Properties
Chemical formula
 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]
Solubility in water
 good, also good in Ethyl acetate[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Chemical compound

Lotaustralin is a cyanogenic glucoside found in small amounts in Fabaceae austral trefoil (Lotus australis),[1] cassava (Manihot esculenta), lima bean (Phaseolus lunatus),[2] roseroot (Rhodiola rosea)[3] and white clover (Trifolium repens),[4] 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

  1. ^ a b c Shmuel Yannai: Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. CRC Press, 2003, ISBN 978-1-58488-416-3, p. 688
  2. ^ 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. PMC 1077184. PMID 16667698.
  3. ^ 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. PMID 15351122.
  4. ^ "Notes on poisoning: Trifolium repens". Canadian Poisonous Plants Information System. May 30, 2006. Archived from the original on June 10, 2011. Retrieved 2007-02-11.