Chemistry: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 Y
3D model (JSmol)	Interactive image
ChemSpider	390193 N
PubChem CID	441467
UNII	P588137A94 Y
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
SMILES 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)
Solubility in water	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).
N verify (what is YN ?)
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.