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[1]
Melting point 189–190 °C (372–374 °F; 462–463 K)[1]
Soluble in hot water[1]
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[2] and upon ripening it is hydrolyzed by the action of the enzyme β-glucosidase which releases vanillin,[3][4] the major contributor to the aroma and flavor of vanilla. Vanillin is further released from glucovanillin during the curing process of vanilla production.[5]

Glucovanillin has weak antibacterial properties and has served as a lead compound for the development of more potent antibactierial compounds.[6]

References

  1. ^ a b c 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.

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