Sinalbin References

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;
UNII	MZ3RB28MCY ;
	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). verify ( what is ?) 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. The half-life of the isothiocyanate depends on the pH of the solution – the longest time is 321 minutes at pH 3, and the shortest is 6 minutes 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.

[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.

[1]

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