glucovanillin
{{Chembox
| ImageFile = Glucovanillin v2.svg
| ImageSize = 200px
| ImageAlt =
| IUPACName = 3-Methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzaldehyde
| OtherNames = {{bulleted list|Vanilloside | Vanillin 4-O-β-D-glucoside }}
| Section1 = {{Chembox Identifiers
| CASNo = 494-08-6
| CASNo_Ref = {{Cascite|correct|CAS}}
| ChEBI = 179508
| ChemSpiderID = 4954574
| KEGG = C19808
| PubChem = 6452133
| UNII = H81U1KBS6E
| SMILES = COC1=C(C=CC(=C1)C=O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
| 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
| InChIKey = LPRNQMUKVDHCFX-RKQHYHRCSA-N
}}
| Section2 = {{Chembox Properties
| C = 14 | H = 18 | O = 8
| Appearance = Crystalline solid{{cite book | title = Merck Index | edition = 11th | id = 4359. Glucovanillin | page = 701 }}
| Density =
| MeltingPtC = 189-190
| BoilingPt =
| Solubility = Soluble in hot water
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
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{{cite journal | doi = 10.1093/aob/mcg150 | title = Localization of β-D-Glucosidase Activity and Glucovanillin in Vanilla Bean (Vanilla planifolia Andrews) | date = 2003 | last1 = Odoux | first1 = E. | last2 = Escoute | first2 = J. | last3 = Verdeil | first3 = J. L. | last4 = Brillouet | first4 = J. M. | journal = Annals of Botany | volume = 92 | issue = 3 | pages = 437–444 | pmid = 12871846 | pmc = 4257512 }} and upon ripening it is hydrolyzed by the action of the enzyme β-glucosidase which releases vanillin,{{cite journal | doi = 10.1111/j.1365-2621.1943.tb18011.x | title = ACTION OF a β-GLUCOSIDASE IX THE CURING OF VANILLA | date = 1943 | last1 = Arana | first1 = Francisca E. | journal = Journal of Food Science | volume = 8 | issue = 4 | pages = 343–351 }}{{cite journal | title = Changes in vanillin and glucovanillin concentrations during the various stages of the process traditionally used for curing Vanilla fragrans beans in Reunion | author = Odoux, Eric | date = 2000 | journal = Fruits | volume = 55 | issue = 2 | pages = 119–125 }} the major contributor to the aroma and flavor of vanilla. Vanillin is further released from glucovanillin during the curing process of vanilla production.{{cite journal | doi = 10.1021/jf00058a019 | title = Determination of Glucovanillin and Vanillin in Cured Vanilla Pods | date = 1995 | last1 = Voisine | first1 = Richard | last2 = Carmichael | first2 = Lucie | last3 = Chalier | first3 = Pascale | last4 = Cormier | first4 = Francois | last5 = Morin | first5 = Andre | journal = Journal of Agricultural and Food Chemistry | volume = 43 | issue = 10 | pages = 2658–2661 | bibcode = 1995JAFC...43.2658V }}
Glucovanillin has weak antibacterial properties and has served as a lead compound for the development of more potent antibactierial compounds.{{cite journal | doi = 10.1016/j.fitote.2023.105475 | title = Nature-inspired synthesis of antibacterial glucovanillin derivatives | date = 2023 | last1 = Masota | first1 = Nelson E. | last2 = Ohlsen | first2 = Knut | last3 = Meinel | first3 = Lorenz | last4 = Holzgrabe | first4 = Ulrike | journal = Fitoterapia | volume = 167 | pmid = 36940919 }}