Vanillin glucoside

Sommer J, Schroeder C, Stoeckigt J (1997) In vivo formation of vanillin glucoside. Plant Cell Tissue Organ Cult 50 119-123... 

B Vanillin glucoside (T3, grey zone at R 0.5 — A) reported in the literature as well as the flavonoids show a strong quenching in irV-254n rn. 

FIGURE 8.6 The conversion of vanillin glucosides to free vanillin. 

Contains up to about 8% triticin (a finctosan) 2-3% inositol and mannitol 1.5% fixed oil vitamins A and B glycosides (e.g., vanillin glucoside) mucilaginous substances ash with high silicon and iron contents and small amount of volatile oil (up to ca. 0.05%) among others (list and horhammer). ... 

CaH803. Fine white needles, m.p. 82°C, b.p. 285°C, strong vanilla odour, characteristic taste. It occurs extensively in nature, and is the odoriferous principle of the vanilla pod it can be obtained from the glucoside coniferin. Vanillin is made commercially from the ligno-sulphonic acid obtained as a by-product in the manufacture of wood pulp. It is one of the most important flavouring and perfuming... 

The long fermenting process converts several glucosides into glucose, vanillin, and other complex aromatic flavors. The vanilla beans can be further processed by extracting soluble compounds in ethanol and water mixtures, resulting in vanilla extract. 

VANILLIN. Vanillin, [CAS 121-35-5]. CgHgCL, a natural product, can be found as a glucoside (ghicovanillin) in vanilla beans, at concentrations of about 2%. It can be extracted with water, alcohol, or other organic solvents. Approximately 250 by-products have been identified m natural vanilla, out of which 26 are present at levels in excess of 1 ppm. The balance of all these products contributes to the subtle taste of vanilla beans, The vanilla bean contains about 2% vanillin, but the 10% extract prepared from beans has several times lire strength of a solution of 2% vanillin. The best known natural source of vanillin is the vanilla plant, Vanilla planifolia A., which belongs to the orchid family. It is cultivated mainly in Mexico, Madagascar, Reunion, Java, and Tahiti. 

The flavoring vanillin occurs naturally as glucovanillin (a glucoside) in the vanilla bean (Section 20-5). It is made commercially in several ways. One is from eugenol, itself a constituent of several essential oils ... 

A more complex pathway was proposed by Funk and Brodelius (1990a,b, 1992), where caffeic acid was first methylated at the 4-posi-tion, followed by the 3-position to produce 3,4-dimethoxycinnamic acid, which was then demethylated at the 4-position, prior to a glucosylation step. Side-chain cleavage was proposed to occur at a late stage to produce vanillic acid (or its /Tn-glucoside), which was then reduced to vanillin (Fig. 15.3). 

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