dhurrin

Also 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.

Chemical data

Formula: C14H17NO7
Molecular weight: 311.29 g/mol
IUPAC name: (2S)-2-(4-hydroxyphenyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
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
InChIKey: NVLTYOJHPBMILU-YOVYLDAJSA-N
XLogP: -0.9
Polar surface area: 143 Å²
H-bond donors: 5
H-bond acceptors: 8
Formal charge: 0

via PubChem

Wikidata facts

Mass: 311.100502

Show 4 more facts

found in taxon: Hakea bucculenta
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

Encyclopedic overview

7 sections

Contents

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= }}

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