Lotaustralin

Lotaustralin
Names


IUPAC name (2R)-2-methyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}butanenitrile
Identifiers
CAS Number	534-67-8^Y
3D model (Jmol)	Interactive image
ChemSpider	390193^N
PubChem	441467
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)^[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).
N verify (what is ^YN ?)
Infobox references

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 2 3 Shmuel Yannai: Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. CRC Press, 2003, ISBN 978-1-58488-416-3, 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. PMC 1077184. PMID 16667698.
↑ 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.
↑ "Notes on poisoning: Trifolium repens". Canadian Poisonous Plants Information System. May 30, 2006. Retrieved 2007-02-11.

Glycosides

Bond	O-glycosidic bond N-glycosidic bond S-glycosidic bond C-glycosidic bond

Geometry	α-Glycoside β-Glycoside 1,4-Glycoside 1,6-Glycoside

Glycone	Fructoside Galactoside Glucoside Glucuronide Rhamnoside Riboside

Aglycone	Alcoholic glycoside Cardiac glycoside Bufadienolide Cardenolide Cyanogenic glycoside Glycosylamine Phenolic glycoside Anthraquinone glycoside Coumarin glycoside Flavonoid glycoside Saponin Steviol glycoside Thioglycoside

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