Sinalbin

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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
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.039.606 Edit this at Wikidata
UNII
  • 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 ☒N
    Key: WWBNBPSEKLOHJU-BXLHIMNRSA-N ☒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
  • 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
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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Sinalbin is a

pungent taste.[1]

Sinalbin is metabolised to form the mustard oil 4-hydroxybenzyl

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

  1. ^ (in French) RICHARD H. Arômes alimentaires Document de cours Archived 2007-02-14 at the Wayback Machine
  2. PMID 16248567
    .
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