Glucoerucin

Glucoerucin Property

Density 

1.68±0.1 g/cm3(Predicted)

pka

-2.91±0.18(Predicted)

InChI

InChI=1/C12H23NO9S3/c1-23-5-3-2-4-8(13-22-25(18,19)20)24-12-11(17)10(16)9(15)7(6-14)21-12/h7,9-12,14-17H,2-6H2,1H3,(H,18,19,20)/b13-8+/t7-,9-,10+,11-,12+/s3

InChIKey

GKUMMDFLKGFCKH-OQSPNCFYNA-N

SMILES

[C@@H]1([C@H](O)[C@H]([C@H](O)[C@@H](CO)O1)O)S/C(=N/OS(=O)(=O)O)/CCCCSC |&1:0,1,3,4,6,r|

Hazard and Precautionary Statements (GHS)

Glucoerucin Chemical Properties,Usage,Production

Description

Glucoerucin is mainly present in cruciferous or brassica vegetables, such as broccoli, cabbage, cauliflower, rapeseed, and mustard. The reason why arugula is bitter and spicy, and even why mustard is pungent, is in fact because they belong to the cruciferous vegetables family, which contains thioglucosides and sesquiterpene glycosides. When chewed and broken by the teeth, sesquiterpene glycosides can be hydrolyzed by their own endogenous myrosinase (black mustard enzyme) to generate sesquiterpenes. Under certain conditions, these can be converted into radish sulfide (raphanin) through interaction with sulfur-containing compounds. Both types of metabolites possess a certain degree of bitterness and strong pungent irritating odor, along with some sulfide taste characteristics.

Uses

Glucoerucin is an aryl hydrocarbon receptor antagonist and is the 4-methylthio-butyl glucosinolate found in the seeds of Eruca sativa Mill[1].

References

[1] Gmelin R, et al. Isolierung von 4-Methylthiobutylglucosinolat (Glucoerucin) aus Samen von Eruca sativa Mill [Isolation of 4-methylthiobutylglucosinolate (glucoerucin) from seeds of Eruca sativa Mill]. Arch Pharm Ber Dtsch Pharm Ges. 1970 Apr;303(4):330-4. DOI:10.1002/ardp.19703030407
[2] R. IORI. ChemInform Abstract: Formation of Glucoraphanin by Chemoselective Oxidation of Natural Glucoerucin: A Chemoenzymatic Route to Sulforaphane.[J]. ChemInform, 2010, 30 32. DOI:10.1002/chin.199932223.
[3] R. IORI . Corrigendum to “Formation of glucoraphanin by chemoselective oxidation of natural glucoerucin: a chemoenzymatic route to sulforaphane” (Bioorg. Med. Chem. Lett. 1999, 9 1047–1048)[J]. Bioorganic & Medicinal Chemistry Letters, 2000, 10 2: Page 197. DOI:10.1016/S0960-894X(99)00665-4.
[4] AHMAD FAIZAL ABDULL RAZIS . Up-regulation of cytochrome P450 and phase II enzyme systems in rat precision-cut rat lung slices by the intact glucosinolates, glucoraphanin and glucoerucin[J]. Lung Cancer, 2011, 71 3: Pages 298-305. DOI:10.1016/j.lungcan.2010.06.015.
[5] JESSICA BARILLARI. Direct Antioxidant Activity of Purified Glucoerucin, the Dietary Secondary Metabolite Contained in Rocket (Eruca sativa Mill.) Seeds and Sprouts[J]. Journal of Agricultural and Food Chemistry, 2005, 53 7: 2475-2482. DOI:10.1021/jf047945a.