Sinalbin

Sinalbin
IUPAC name [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2-(4-hydroxyphenyl)-N-sulfooxyethanimidothioate
Other names Glucosinalbin; 4-Hydroxybenzyl glucosinolate; Glucosinalbate
Identifiers
CAS number	19253-84-0 Y
PubChem	656568
	Jmol-3D images	{{#if:O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](S/C(CC2=CC=C(O)C=C2)=N\OS(O)(=O)=O)[C@@H]1O|Image 1
SMILES O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](S/C(CC2=CC=C(O)C=C2)=N\OS(O)(=O)=O)[C@@H]1O
Properties
Molecular formula	C14H19NO10S2
Molar mass	425.43 g mol−1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Sinalbin is a glucosinolate found in the seeds of white mustard, Sinapis alba, and in many wild plant species. In contrast to mustard from black mustard (Brassica nigra) seeds which contain sinigrin, mustard from white mustard seeds has only a weakly pungent taste.^[1]

Sinalbin is metabolised to form the mustard oil 4-hydroxybenzyl isothiocyanate by the enzyme myrosinase. The less sharp taste of white mustard is because 4-hydroxybenzyl isothiocyanate is unstable, with a half-life of one or a few hours. It degrades to 4-hydroxybenzyl alcohol and a thiocyanate ion, which are not pungent. Glucobrassicin is a structurally related glucosinolate that likewise yields a non-pungent isothiocyanate due to reaction with water.

References