Sinalbin

Sinalbin
Names
	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 ;
3D model (JSmol)	Interactive image;
ChemSpider	7875243 ;
ECHA InfoCard	100.039.606
PubChem CID	656568;
	InChI InChI=1S/C14H19NO10S2/c16-6-9-11(18)12(19)13(20)14(24-9)26-10(15-25-27(21,22)23)5-7-1-3-8(17)4-2-7/h1-4,9,11-14,16-20H,5-6H2,(H,21,22,23)/b15-10+/t9-,11-,12+,13-,14+/m1/s1 Key: WWBNBPSEKLOHJU-BXLHIMNRSA-N ; InChI=1/C14H19NO10S2/c16-6-9-11(18)12(19)13(20)14(24-9)26-10(15-25-27(21,22)23)5-7-1-3-8(17)4-2-7/h1-4,9,11-14,16-20H,5-6H2,(H,21,22,23)/b15-10+/t9-,11-,12+,13-,14+/m1/s1 Key: WWBNBPSEKLOHJU-BXLHIMNRBZ;
	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
Chemical formula	C14H19NO10S2
Molar mass	425.42 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	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 and degrades to 4-hydroxybenzyl alcohol and a thiocyanate ion, which are not pungent. Half-life of the isothiocyanate is depending on pH of the solution – longest time is 321 minutes at pH 3, and lowest is 6 min at pH 6.5.[2] Glucobrassicin is a structurally related glucosinolate that likewise yields a non-pungent isothiocyanate due to reaction with water.

References

(in French) RICHARD H. Arômes alimentaires Document de cours Archived 2007-02-14 at the Wayback Machine
Borek, Vladimir; Morra, Matthew J. (2005-09-24). "Ionic Thiocyanate (SCN – ) Production from 4-Hydroxybenzyl Glucosinolate Contained in Sinapis alba Seed Meal". Journal of Agricultural and Food Chemistry. 53 (22): 8650–8654. doi:10.1021/jf051570r. PMID 16248567.

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[1] (in French) RICHARD H. Arômes alimentaires Document de cours Archived 2007-02-14 at the Wayback Machine

[2] Borek, Vladimir; Morra, Matthew J. (2005-09-24). "Ionic Thiocyanate (SCN – ) Production from 4-Hydroxybenzyl Glucosinolate Contained in Sinapis alba Seed Meal". Journal of Agricultural and Food Chemistry. 53 (22): 8650–8654. doi:10.1021/jf051570r. PMID 16248567.