lotaustralin

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.

Chemical data

Formula: C11H19NO6
Molecular weight: 261.27 g/mol
IUPAC name: (2R)-2-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutanenitrile
SMILES: CC[C@](C)(C#N)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
InChIKey: WEWBWVMTOYUPHH-QHAQEBJBSA-N
XLogP: -1.1
Polar surface area: 123 Å²
H-bond donors: 4
H-bond acceptors: 7
Formal charge: 0

via PubChem

Wikidata facts

Subclass of: carbohydrate
Has part: carbon
Mass: 261.121237

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found in taxon: Rhodiola rosea
chemical formula: C₁₁H₁₉NO₆
canonical SMILES: CCC(C)(C#N)OC1C(C(C(C(O1)CO)O)O)O
isomeric SMILES: CC[C@](C)(C#N)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
Commons category: Lotaustralin

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Encyclopedic overview

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References

{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 424328298 | ImageFile1 = Lotaustralin structure.svg | ImageSize1 = | ImageFile2 = Lotaustralin 3D sticks.png | IUPACName = (2R)-2-(β-D-Glucopyranosyloxy)-2-methylbutanenitrile | SystematicName = (2R)-2-Methyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanenitrile | OtherNames = |Section1= |Section2= |Section3= }}

Excerpted from Wikipedia’s “lotaustralin” article, available under the CC BY-SA 4.0 licence.

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