Glucovanillin

Vanilloside, also known as avenein or glucovanillin, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Vanilloside exists as a solid, soluble (in water), and a very weakly acidic compound (based on its pKa). Within the cell, vanilloside is primarily located in the cytoplasm. Vanilloside is a very mild, bitter, and vanilla tasting compound that can be found in cereals and cereal products and oat. This makes vanilloside a potential biomarker for the consumption of these food products. Glucovanillin is a natural product that is found in the papillae of various plants and in the bark of conifers. It is an inhibitor of bacterial growth, but its mechanism of action has not been determined. Glucovanillin has been shown to exhibit anti-inflammatory properties, which may be due to its inhibition of prostaglandin synthesis. In tissue culture experiments, glucovanillin inhibited the growth of Candida albicans and Helicobacter pylori. The active form, vanillin, can be produced by hydrolysis of glucovanillin with hydrochloric acid or by microbial metabolism. The optimum pH for glucovanillin production is between 5 and 6, with a maximum at about pH 4.5. The surface methodology for detecting glucovanillin involves measuring the reaction solution's absorption spectrum at 260 nm after adding hydrochloric acid and sodium hydroxide to react with the sample. CAS Number 494-08-6 Product Name Glucovanillin IUPAC Name 3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzaldehyde Molecular Formula C14H18O8 Molecular Weight 314.29 g/mol InChI 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 InChI Key LPRNQMUKVDHCFX-UHFFFAOYSA-N SMILES COC1=C(C=CC(=C1)C=O)OC2C(C(C(C(O2)CO)O)O)O Synonyms 4-(beta-D-Glucopyranosyloxy)-3-methoxybenzaldehyde Canonical SMILES COC1=C(C=CC(=C1)C=O)OC2C(C(C(C(O2)CO)O)O)O Isomeric 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 COA: Product name: Glucovanillin, 4-(beta-D-Glucopyranosyloxy)-3-methoxybenzaldehyde M.F.: C 14 H 18 O 8 M.W.: 314.29 CAS: 494-08-6 Items Standards Results Appearance White crystals or powder Positive Solubility Easily soluble in water, insoluble in ether Complies Appearance of solution Dissolve0.5gin 10mLof water, and the solution should be clear Complies Identification IR and TLC Complies MS and NMR Should Comply Complies M.P. 180 ? ~ 190 ? 185 ? ~188 ? Loss weight on Dryness Min.1% 0.2% Residue on ignition Max. 0.5% 0.1% TLC Should be one spot one spot Heavy metal Max.50ppm Complies Any other impurity Max. 0.5% Complies Assay Min. 98% 99.2%