P-Vanillin

Synonyms m-Anisaldehyde Vanillic aldehyde Lioxin 3-Methoxy-4-hydroxybenzaldehyde p-Hydroxy-m-methoxybenzaldehyde Lioxin Vanillaldehyde Vanillic aldehyde 2-Methoxy-4-formylphenol 3-Methoxy-4-hydroxybenzalde-hyde Vanilla Protocatechualdehyde, methyl- Zimco p-Vanillin Methylprotcatechuic aldehyde Methylprotocatechuic aldehyde Chemical/Pharmaceutical/Other Class Essential oil... 

H.56) (H.56) Benzaldehyde, 4-hydroxy-3-methoxy-, 4-hydroxy-3-methoxybenzaldehyde, 4-formyl-2-methoxyphenol, vanillin, p-vanillin 1121-33-5] FEMA 3107... 

METHYLPROTOCATECHUALDEHYDE VANILLA VANILLALDEHYDE VANILLIC ALDEHYDE p-VANILLIN ZIMCO... 

Z-Me ether CjHgOg. MW, 196. Prisms + CgHe from CgHg. M.p. 133-4° Heat above m.p. —> vanillin. 

CgHeOa. White crystals m.p. 37°C, b.p. 263°C. Occurs associated with vanillin. Obtained on oxidation of various natural products such as piperine. Used extensively in soap perfumery. 

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... 

Substances suitable for the estimation acetanilide, sucrose, glucose, cinnamic acid, diphenyl amine, salicylic acid, vanillin, />"bromoacetanilide, toluene p-sul phonamide. 

Other commonly occurring chemical groups ia essential oils iaclude aromatics such as P-phenethyl alcohol, eugenol, vanillin, ben2aldehyde, cinnamaldehyde, etc heterocycHcs such as iadole (qv), pyra2iaes, thia2oles, etc hydrocarbons (Liaear, branched, saturated, or unsaturated) oxygenated compounds such as alcohols, acids, aldehydes, ketones, ethers and macrocyclic compounds such as the macrocyclic musks, which can be both saturated and unsaturated. 

Karrer and Schmid have examined the water-soluble constituents in poppy straw after extraction of the alkaloids, and have recorded the presence of -hydroxybenzaldehyde, vanillin, -hydroxystyrene, meconin and the following acids fumaric, dZ-lactic, benzoic, -hydroxycinnamic, p-hydroxybenzoic, 2-hydroxycinchoninic, vanillic, phthalic, hemipinic and m-hemipinic, with a more highly unsaturated, carboxylic acid J, b.p. 170-570-02 mm., and three unidentified substances Fa , m.p. 271-2° Wx, m.p. 310° (dec.) and Q, m.p. 260° the two latter are free from nitrogen and contain no methoxyl. 

B. H2SO4.6HgO, crystallises with difficulty in prismatic rods, m.p.>310°, Wd + 52-94° (HgO) the oxalate, B. HgCg04, separates from alcohol in colourless leaflets, m.p. 235° dec.), [a]n + 55-6° (HgO). The base gives a pink colour, changing to bluish-violet with vanillin and hydrochloric acid, and a brown, changing through purple to blue with sulphuric acid. 

Eupe also found that one osmophore can be replaced by another without greatly altering the type of the odour, thus vanilline, p-nitro-guaiacol, and p-cyanoguaiacol all have similar odours but varying in strength. 

This latter, when heated at 150° to 160° C. with dimethyl-p-toluidine is decomposed with the production of vanillin. 

The total phenolic content in XRPP was 1.10%. The major components were found to be p-hydroxybenzoic acid (0.44%), vanillin (0.19%), syringic acid (0.13%), and syringaldehyde (0.13%). The contents of p-hydroybenzaldehyde, vanillic acid and ferulic acid were 0.032, 0.015 and 0.020%, respectively. Gallic acid, protocatechuic acid and cinnamic acid were detected in trace amounts. 

In some cases we may find it expeditious and convenient to remove an undesired impurity (or even the desired product) azeotropically and then deal with the streams. For example, in the separations of vanillin from close-boiling substances such as p-hydroxybenzaldehyde, azeotropic distillation with dibenzylether is claimed to be useful (Dimian and Kersten, 1997). 

Zhao, L.-Q., Sun, Z.-H., Zheng, P. and He, J.-Y. (2006) Biotransformation of isoeugenol to vanillin by Bacillus fusiformis CGMCC1347 with the addition of resin HD-8. Process Biochemistry (Barking, London, England), 41, 1673-1676. 

Treatment of suberin with nitrobenzene generates vanillin, p-hydroxy benz-aldehyde, but not much syringaldehyde that arises mostly from lignin. 

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