Dhurrin

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Dhurrin
Dhurrin.svg
Names
IUPAC name
(2S)-2-(4-Hydroxyphenyl)-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]oxy]acetonitrile
Other names
(S)-4-Hydroxymandelnitrile-β-D-glucopyranoside; (S)-(β-D-Glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile
Identifiers
499-20-7 YesY
ChemSpider 141737 N
Jmol-3D images Image
PubChem 161355
Properties
C14H17NO7
Molar mass 311.29 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

Dhurrin is a cyanogenic glycoside occurring in plants. Its biosynthesis has been elucidated.[1][2] Dhurrin is hydrolyzed in the stomach of an insect into a carbohydrate and aglycone. The aglycone is unstable and releases hydrogen cyanide.

References[edit]

  1. ^ Nielsen JS, Moller BL (1999). "Biosynthesis of cyanogenic glucosides in Triglochin maritima and the involvement of cytochrome P450 enzymes". Arch. Biochem. Biophys. 368 (1): 121–130. doi:10.1006/abbi.1999.1258. PMID 10415119. 
  2. ^ Nielsen JS, Moller BL (2000). "Cloning and expression of cytochrome P450 enzymes catalyzing the conversion of tyrosine to p-hydroxyphenylacetaldoxime in the biosynthesis of cyanogenic glucosides in Triglochin maritima". Plant Physiol. 122 (4): 1311–21. doi:10.1104/pp.122.4.1311. PMC 58967. PMID 10759528.