Gluconasturtiin

Gluconasturtiin
Names
	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 ;
3D model (JSmol)	Interactive image;
ChemSpider	7827541 ;
ECHA InfoCard	100.231.959
PubChem CID	9548618;
UNII	163ENC977A ;
CompTox Dashboard (EPA)	DTXSID70964468 ;
	InChI InChI=1S/C15H21NO9S2/c17-8-10-12(18)13(19)14(20)15(24-10)26-11(16-25-27(21,22)23)7-6-9-4-2-1-3-5-9/h1-5,10,12-15,17-20H,6-8H2,(H,21,22,23)/b16-11+/t10-,12-,13+,14-,15+/m1/s1 Key: CKIJIGYDFNXSET-MFIRQCQASA-N ; InChI=1/C15H21NO9S2/c17-8-10-12(18)13(19)14(20)15(24-10)26-11(16-25-27(21,22)23)7-6-9-4-2-1-3-5-9/h1-5,10,12-15,17-20H,6-8H2,(H,21,22,23)/b16-11+/t10-,12-,13+,14-,15+/m1/s1 Key: CKIJIGYDFNXSET-MFIRQCQABS;
	SMILES O=S(=O)(O)O\N=C(\S[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)CCc2ccccc2;
Properties
Chemical formula	C15H21NO9S2
Molar mass	423.45 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

Gluconasturtiin (phenethylglucosinolate) is one of the most widely distributed glucosinolates in the cruciferous vegetables, 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

^ (in French) RICHARD H. Arômes alimentaires PDF Document Archived February 14, 2007, at the Wayback Machine
^ 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

References

See also