Lotaustralin

Lotaustralin
Identifiers
CAS number 534-67-8
PubChem 441467
Jmol-3D images Image 1
Properties
Molecular formula C11H19NO6
Molar mass 261.27 g mol−1
Appearance colorless needles
Density 1.36 g·cm-3
Melting point

139 °C [1]
Solubility in water good, also good in Ethyl acetate [1]
 Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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. ^ a b c Shmuel Yannai: Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. CRC Press, 2003, ISBN 9781584884163, 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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1077184.  Full text at PMC: 1077184
  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. http://www.cbif.gc.ca/pls/pp/ppack.info?p_psn=258&p_type=all&p_sci=sci&p_x=pp. Retrieved 2007-02-11. 
Bond
Geometry
Glycone
Aglycone
biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i