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
3D model (JSmol)
ChemSpider
UNII
  • 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
C11H19NO6
Molar mass 261.27 g/mol
Appearance colorless needles
Density 1.36 g·cm−3
Melting point 139 °C (282 °F; 412 K)
good, also good in Ethyl acetate
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

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


This page was last updated at 2024-01-27 19:42 UTC. Update now. View original page.

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