Alcohol vanillin

Reduction of vanillin by means of platinum black in the presence of ferric chloride gives vanillin alcohol in excellent yields. In 1875, Tiemann reported the reduction of vanillin to vanillin alcohol by using sodium amalgam in water. The yields were poor, however, and there were a number of by-products. High yields of vanillin alcohol have been obtained by electrolytic reduction. 

Vanillin Suga.r, This product is prepared by dry mixing or impregnating the sugar with a vanillin alcohol solution and evaporating the alcohol. However, modem techniques increasingly involve grinding the sucrose and vanillin mixture very finely. 

A large amount of research has been done on developing products from the waste sulfite liquor, and some success has been achieved. Vanillin, alcohol, and torula yeast can be produced as by-products, and the lignosulfonates are used as viscosity modifiers in drilling muds and for similar purposes. However, the... 

Later, Tressl et al. (1976) also proceeded to the thermic degradation (2 h, 200 JC) of ferulic acid (H.87) and identified the same phenols as Fiddler et al., plus 4-isopropylguaiacol and vanillin alcohol (4-hydroxy-3-methoxybenzenemethanol) which have not been found in coffee. For isoeugenol (H.38), the formula is written as the (E)-( trans -) isomer, but nothing was specified in the text. Tressl et al. (1976) also published the results of thermal decomposition of cinnamic, p-coumaric (H.84) and sinapic (H.90) acids. Many of the simple phenols (and other aromatic compounds) formed have also been identified in roasted coffee volatiles. A thermic fragmentation of quinic acid (E.62) has shown that simple acids, phenols and polyphenols originate from this precursor (Tressl et al., 1978a). 

Guaiacol has a very characteristic odour and burning taste its medicinal properties are identical with those of creosote. Used in the preparation of vanillin and paparvarin and for denaturing alcohol. 

Gunzherg s reagent (detection of HCl in gastric juice) dissolve 4 g of phloroglucinol and 2 g of vanillin in 100 mL of absolute alcohol use only a freshly prepared solution. 

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. 

Many other recovery alternatives have been proposed that iaclude ion exchange (qv), pyrolysis, and wet combustion. However, these have not gained general acceptance. A limited number of calcium-based mills are able to utilize their spent pulpiag liquors to produce by-products such as lignosulfates for oil-weU drilling muds, vanillin, yeast, and ethyl alcohol (see PETROLEUM Vanillin). 

Solubility. SolubiUty in water is less than 2% the solubiUty in ethanol is given by the ratio one part vanillin to two parts alcohol. Certain manufacturing processes require that the product be in Hquid form. Depending on the appHcation, the solvent must be chosen in accordance with the manufacturing process and regulation requirements. 

The food flavor industry is the largest user of vanillin, an indispensable ingredient in chocolate, candy, bakery products, and ice cream. Commercial vanilla extracts are made by macerating one part of vanilla beans with ten parts of 40—50% alcohol. Although vanillin is the primary active ingredient of vanilla beans, the full flavor of vanilla extract is the result of the presence of not only vanillin but also other ingredients, especially Httle-known resinous materials which contribute greatly to the quaUty of the flavor. 

In detergent perfumes, the stabiUty of vanillin is not always certain. It depends on the association made with other raw materials, eg, with patchouli, frankincense, cloves, most of the animal notes, and such chemicals as amyl saUcylate, methyl ionones, heflotropin, gamma undecalactone, linalool, methyl anthrarulate, benzyl acetate, phenyl ethyl alcohol, cedar wood derivatives, oak mosses, coumarin, benzoin. Pern balsam, and cistus derivatives. In some cases, these mixtures can cause discoloration effects. 

It has also been proposed that under the acidic conditions found ia whiskeys, ethanol reacts with lignin (qv) to reduce an alcohol-soluble form of lignin (ethanol lignin). This can be converted into coniferyl alcohol, which can be oxidized to coniferaldehyde. The partial oxidation of ethanol lignin can produce siaapic and coniferyl alcohols that can be converted to syfingaldehyde and vanillin, respectively (8). 

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. 

Essence of Vanilla.—The substance sold under this name is, properly, a spirituous extract of the vanilla bean. Many samples, however, are little more than alcoholic solutions of artificial vanillin, coloured with caramel. Some samples, which cannot be described as adulterated, contain a little coumarin or other odorous substance, added to varj- the characteristic vanillin odour and flavour somewhat. 

Commercial essence of vanilla is usually made with about 5 per cent, of vanillas, the menstruum varying in strength from 40 to 50 per cent, alcohol in the best varieties. Sugar is sometimes added, but not always. The average vanillin content is O l to 0 2. Much higher values than these indicate the presence of synthetic vanillin. 

Heliotropin melts at 37°, but its perfume is injured by exposure to a temperature several degrees below this, and it should always be stored in cool dark places. In very hot weather the stock may with advantage be kept dissolved in alcohol, ready for use. Its perfume is a powerful heliotrope odour, and is improved by blending it with a little coumarin or vanillin, or with bergamot, lemon, or neroli oil. Attention should be drawn to the fact that the fancy perfumes whose names resemble heliotrope are usually mixtures of heliotropin—the cheaper ones being chiefly acetanilide, the more expensive ones containing vanillin or coumarin. 

For the estimation of vanillin, T. von Fallenburg proposes to make use of the colour produced by treating a dilute aqueous solution with isobutyl alcohol and concentrated sulphuric acid. Five c.c. of the solution are mixed with 5 c.c. of a 1 per cent isobutyl alcohol solution in 95 per cent, alcohol, and 25 c.c. concentrated sulphuric acid, the colour produced being compared after forty-five minutes with that given by known amounts of vanillin. 

Aryl alcohol oxidase from the ligninolytic fungus Pleurotus eryngii had a strong preference for benzylic and allylic alcohols, showing activity on phenyl-substituted benzyl, cinnamyl, naphthyl and 2,4-hexadien-l-ol [103,104]. Another aryl alcohol oxidase, vanillyl alcohol oxidase (VAO) from the ascomycete Penicillium simplicissimum catalyzed the oxidation of vanillyl alcohol and the demethylation of 4-(methoxymethyl)phenol to vanillin and 4-hydro-xybenzaldehyde. In addition, VAO also catalyzed deamination of vanillyl amine to vanillin, and hydroxylation and dehydrogenation of 4-alkylphenols. For the oxidation of 4-alkylphenol, the ratio between the alcohol and alkene product depended on the length and bulkiness of the alkyl side-chain [105,106]. 4-Ethylphenol and 4-propylphenol, were mainly converted to (R)-l-(4 -hydroxyphenyl) alcohols, whereas medium-chain 4-alkylphenols such as 4-butylphenol were converted to l-(4 -hydroxyphenyl)alkenes. 

Valeraldehyde, p28 Valeric acid, p38 Valeronitrile, p35 Valeryl chloride, p45 Vanillic acid, hi43 Vanillin, hl42 Vanillyl alcohol, hl45 Veratraldehyde, d492 Veratric acid, d496 Veratrole, d493 Veronal, d330... 

The biocatalytic reduction of carboxylic acids to their respective aldehydes or alcohols is a relatively new biocatalytic process with the potential to replace conventional chemical processes that use toxic metal catalysts and noxious reagents. An enzyme known as carboxylic acid reductase (Car) from Nocardia sp. NRRL 5646 was cloned into Escherichia coli BL21(DE3). This E. coli based biocatalyst grows faster, expresses Car, and produces fewer side products than Nocardia. Although the enzyme itself can be used in small-scale reactions, whole E. coli cells containing Car and the natural cofactors ATP and NADPH, are easily used to reduce a wide range of carboxylic acids, conceivably at any scale. The biocatalytic reduction of vanillic acid to the commercially valuable product vanillin is used to illustrate the ease and efficiency of the recombinant Car E. coli reduction system." A comprehensive overview is given in Reference 6, and experimental details below are taken primarily from Reference 7. 

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