dhurrin
Sign in to saveAlso known as (alphaS)-alpha-(beta-D-glucopyranosyloxy)-4-hydroxybenzeneacetonitrile, (S)-(beta-D-glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile
Dhurrin is a cyanogenic glycoside produced in many plants. Discovered in multiple sorghum varieties in 1906 as the culprit of cattle poisoning by hydrogen cyanide, dhurrin is most typically associated with Sorghum bicolor, the organism used for mapping the biosynthesis of dhurrin from tyrosine. Dhurrin's name is derived from the Arabic word for sorghum.
Wikidata facts
- Mass
- 311.100502
Show 3 more facts
- chemical formula
- C₁₄H₁₇NO₇
- isomeric SMILES
- C1=CC(=CC=C1[C@@H](C#N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O
- canonical SMILES
- C1=CC(=CC=C1C(C#N)OC2C(C(C(C(O2)CO)O)O)O)O
Sources (2)
via Wikidata · CC0
~4 min read
Article
7 sectionsContents
- Biosynthesis
- Regulation in ''Sorghum bicolor''
- Transgenic synthesis
- Toxicity
- Mammals
- As an insect repellent
- References
{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 424742148 | ImageFile=Dhurrin.svg | ImageSize=250px | IUPACName=(S)-(β-D-Glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile | SystematicName=(S)-(4-Hydroxyphenyl){[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile | OtherNames=(S)-4-Hydroxymandelnitrile-β-D-glucopyranoside |Section1= |Section2= |Section3= }}
Dhurrin is a cyanogenic glycoside produced in many plants. Discovered in multiple sorghum varieties in 1906 as the culprit of cattle poisoning by hydrogen cyanide, dhurrin is most typically associated with Sorghum bicolor, the organism used for mapping the biosynthesis of dhurrin from tyrosine. Dhurrin's name is derived from the Arabic word for sorghum.