Glucoberteroin

Glucoberteroin
Names
IUPAC name
[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1E)-6-methylsulfanyl-N-sulfooxyhexanimidothioate
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C13H25NO9S3/c1-24-6-4-2-3-5-9(14-23-26(19,20)21)25-13-12(18)11(17)10(16)8(7-15)22-13/h8,10-13,15-18H,2-7H2,1H3,(H,19,20,21)/b14-9+/t8-,10-,11+,12-,13+/m1/s1
    Key: MEFPHTVXBPLRLX-KHXSHCKASA-N
  • anion: InChI=1S/C13H25NO9S3/c1-24-6-4-2-3-5-9(14-23-26(19,20)21)25-13-12(18)11(17)10(16)8(7-15)22-13/h8,10-13,15-18H,2-7H2,1H3,(H,19,20,21)/p-1/b14-9+/t8-,10-,11+,12-,13+/m1/s1
    Key: MEFPHTVXBPLRLX-KHXSHCKASA-M
  • CSCCCCC/C(=N\OS(=O)(=O)O)/S[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
  • anion: CSCCCCC/C(=N\OS(=O)(=O)[O-])/S[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
Properties
C13H25NO9S3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Glucoberteroin is an organic compound belonging to the group of mustard oil glycosides.

Occurrence

Glucoberteroin occurs in Berteroa incana, in which it was first identified in the 1950s.[1][2] It is also present in broccoli,[3] turnip, and rutabaga.[4]

References

  1. ^ Kjær, Anders; Larsen, Ivan; Gmelin, Rolf; Prydz, Harald (1955), "isoThiocyanates. XIV. 5-Methylthiopentyl isoThiocyanate, a New Mustard Oil Present in Nature as a Glucoside (Glucoberteroin).", Acta Chemica Scandinavica, vol. 9, pp. 1311–1316, doi:10.3891/acta.chem.scand.09-1311
  2. ^ Warwick, S. I.; Francis, A. (2006-10-10), "The Biology of Invasive Alien Plants in Canada. 6. Berteroa incana (L.) DC", Canadian Journal of Plant Science, vol. 86, no. 4, pp. 1297–1309, doi:10.4141/P06-030
  3. ^ Baenas, Nieves; Moreno, Diego A.; García-Viguera, Cristina (2012-11-14), "Selecting Sprouts of Brassicaceae for Optimum Phytochemical Composition", Journal of Agricultural and Food Chemistry, vol. 60, no. 45, pp. 11409–11420, doi:10.1021/jf302863c
  4. ^ Carlson, Diana G.; Daxenbichler, Melvin E.; VanEtten, Cecil H.; Tookey, Harvey L.; Williams, Paul H. (November 1981), "Glucosinolates in crucifer vegetables: turnips and rutabagas", Journal of Agricultural and Food Chemistry, vol. 29, no. 6, pp. 1235–1239, doi:10.1021/jf00108a034
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