Glucovanillin
Iupacname3-Methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzaldehyde
Othernames
  • Vanilloside
  • Vanillin 4-O-β-D-glucoside

Glucovanillin, also known as vanilloside, is a chemical compound found in vanilla beans. Chemically, it is a glucoside composed of glucose and vanillin. Glucovanillin is particularly prevalent in green vanilla beans[1] and upon ripening it is hydrolyzed by the action of the enzyme β-glucosidase which releases vanillin,[2][3] the major contributor to the aroma and flavor of vanilla. Vanillin is further released from glucovanillin during the curing process of vanilla production.[4]

Glucovanillin has weak antibacterial properties and has served as a lead compound for the development of more potent antibactierial compounds.[5]

References

  1. ^ Odoux, E.; Escoute, J.; Verdeil, J. L.; Brillouet, J. M. (2003). "Localization of β-D-Glucosidase Activity and Glucovanillin in Vanilla Bean (Vanilla planifolia Andrews)". Annals of Botany. 92 (3): 437–444. doi:10.1093/aob/mcg150. PMC 4257512. PMID 12871846
  2. ^ Arana, Francisca E. (1943). "ACTION OF a β-GLUCOSIDASE IX THE CURING OF VANILLA". Journal of Food Science. 8 (4): 343–351. doi:10.1111/j.1365-2621.1943.tb18011.x
  3. ^ Odoux, Eric (2000). "Changes in vanillin and glucovanillin concentrations during the various stages of the process traditionally used for curing Vanilla fragrans beans in Reunion". Fruits. 55 (2): 119–125.
  4. ^ Voisine, Richard; Carmichael, Lucie; Chalier, Pascale; Cormier, Francois; Morin, Andre (1995). "Determination of Glucovanillin and Vanillin in Cured Vanilla Pods". Journal of Agricultural and Food Chemistry. 43 (10): 2658–2661. Bibcode:1995JAFC...43.2658V. doi:10.1021/jf00058a019
  5. ^ Masota, Nelson E.; Ohlsen, Knut; Meinel, Lorenz; Holzgrabe, Ulrike (2023). "Nature-inspired synthesis of antibacterial glucovanillin derivatives". Fitoterapia. 167. doi:10.1016/j.fitote.2023.105475. PMID 36940919