Glucovanillin

Glucovanillin
Names
IUPAC name
3-Methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzaldehyde
Other names
  • Vanilloside
  • Vanillin 4-O-β-D-glucoside
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C14H18O8/c1-20-9-4-7(5-15)2-3-8(9)21-14-13(19)12(18)11(17)10(6-16)22-14/h2-5,10-14,16-19H,6H2,1H3/t10-,11-,12+,13-,14-/m1/s1
    Key: LPRNQMUKVDHCFX-RKQHYHRCSA-N
  • COC1=C(C=CC(=C1)C=O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
Properties
C14H18O8
Molar mass 314.290 g·mol−1
Appearance Crystalline solid
Melting point 189–190 °C (372–374 °F; 462–463 K)
Soluble in hot water
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 and upon ripening it is hydrolyzed by the action of the enzyme β-glucosidase which releases vanillin, the major contributor to the aroma and flavor of vanilla. Vanillin is further released from glucovanillin during the curing process of vanilla production.

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

References

  1. 1 2 3 Merck Index (11th ed.). p. 701. 4359. Glucovanillin.
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ 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.
  6. ↑ 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.