Gluconasturtiin

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Gluconasturtiin
IUPAC name

{[3-phenyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6- (hydroxymethyl)-2-tetrahydropyranyl]thio}propylidene]amino} hydrogen sulfate

Other names

Phenethylglucosinolate

Identifiers
CAS number 499-30-9 YesY
PubChem 9548618
ChemSpider 7827541 N
Jmol-3D images {{#if:O=S(=O)(O)O\N=C(\S[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)CCc2ccccc2|Image 1
Properties
Molecular formula C15H21NO9S2
Molar mass 423.461 g/mol
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Gluconasturtiin (phenethylglucosinolate) is one of the most widely distributed glucosinolates in the crucifers, mainly in the roots, and is probably one of the plant compounds responsible for the natural pest-inhibiting properties of growing crucifers, such as cabbage, mustard or rape, in rotation with other crops. This effect of gluconasturtiin is most likely due to its degradation by the plant enzyme myrosinase into phenethyl isothiocyanate, which is toxic to many organisms.

Gluconasturtiin is named from its occurrence in watercress (Nasturtium officinale). Among the vegetables, it is also found in horseradish (Armoracia rusticana) along with sinigrin. Both compounds elicit a pungent taste.[1]

In one investigation of horseradish roots, sinigrin concentration represented 83% and gluconasturtiin 11% of the extracted glucosinolates.[2]

References

  1. ↑ (French) RICHARD H. Arômes alimentaires PDF Document
  2. ↑ XIAN LI, KUSHAD MM (2004) Correlation of glucosinolate content to myrosinase activity in horseradish (Armoracia rusticana). J Agric Food Chem (52)23, pp. 6950-6955

See also

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