Dhurrin

Dhurrin

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
CAS number	499-20-7
PubChem	161355
Jmol-3D images	Image 1
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
Properties
Molecular formula	C₁₄H₁₇NO₇
Molar mass	311.29 g/mol
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

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

Glycosides

Bond	N-glycosidic bond · O-glycosidic bond · S-glycosidic bond

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

Glycone	Glucoside · Fructoside · Glucuronide · Riboside

Aglycone	Alcoholic glycoside · Anthraquinone glycoside · Cardiac glycoside (Bufadienolide, Cardenolide) · Coumarin glycoside · Cyanogenic glycoside · Flavonoid glycoside · Glycosylamine · Phenolic glycoside · Saponin · Steviol glycoside · Thioglycoside

biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i