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Gluconasturtiin information


Gluconasturtiin
Names
IUPAC name
1-S-[(1Z)-3-Phenyl-N-(sulfooxy)propanimidoyl]-1-thio-β-D-glucopyranose
Other names
Phenethyl glucosinolate
Identifiers
CAS Number
  • 499-30-9 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:79347 checkY
ChemSpider
  • 4576506 checkY
ECHA InfoCard 100.231.959 Edit this at Wikidata
PubChem CID
  • 5464032
UNII
  • 163ENC977A checkY
CompTox Dashboard (EPA)
  • DTXSID70964468 Edit this at Wikidata
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 checkY
    Key: CKIJIGYDFNXSET-OOMJLXHVSA-N checkY
SMILES
  • c1ccc(cc1)CC/C(=N/OS(=O)(=O)O)/S[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
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).
Infobox references

Gluconasturtiin or phenethyl glucosinolate 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 due to its degradation by the plant enzyme myrosinase into phenethyl isothiocyanate, which is toxic to many organisms.[1]

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.[2]

  1. ^ Blažević, Ivica; Montaut, Sabine; Burčul, Franko; Olsen, Carl Erik; Burow, Meike; Rollin, Patrick; Agerbirk, Niels (2020). "Glucosinolate structural diversity, identification, chemical synthesis and metabolism in plants". Phytochemistry. 169: 112100. doi:10.1016/j.phytochem.2019.112100. PMID 31771793. S2CID 208318505.
  2. ^ (in French) RICHARD H. Arômes alimentaires PDF Document Archived February 14, 2007, at the Wayback Machine

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Gluconasturtiin

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Gluconasturtiin or phenethyl glucosinolate is one of the most widely distributed glucosinolates in the cruciferous vegetables, mainly in the roots, and...

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Phenethyl isothiocyanate

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isothiocyanate (PEITC) is a naturally occurring isothiocyanate whose precursor, gluconasturtiin is found in some cruciferous vegetables, especially watercress. PEITC...

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Horseradish

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Dietary fiber

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Isothiocyanate

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isothiocyanate Glucotropaeolin is the precursor to benzyl isothiocyanate Gluconasturtiin is the precursor to phenethyl isothiocyanate Glucoraphanin is the precursor...

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Brassicaceae

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Barbarea vulgaris

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named the "NAS-type" (because it is dominated by the glucosinolate glucoNASturtiin. This type has increased resistance to some specialized insects. In...

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mustard. Glucotropaeolin (the precursor to benzyl isothiocyanate) Gluconasturtiin (the precursor to phenethyl isothiocyanate) Glucoraphanin (the precursor...

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Pieris rapae

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plant. An adult female will be sensitive to number of glucosinolates, gluconasturtiin being the most effective glucosinolate stimulants for these sensilla...

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Glucosinolate

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is the precursor of benzyl isothiocyanate Phenethylglucosinolate (gluconasturtiin) is the precursor of phenethyl isothiocyanate (R)-4-(methylsulfiny...

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Saponin

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Betalain

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Phytosterol

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Arame

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Glucobrassicin

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Finally, the hydroximate itself is sulfated creating glucobrassicin. Gluconasturtiin Agerbirk, Niels; Vos, Martin; Kim, Jae Hak; Jander, Georg (2008). "Indole...

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