Synthetic vanillin

Catechol is also obtained from coal coking and from certain wood residues. Vanillin (synthetic vanilla flavoring) is a catechol derivative. Resorcinol and hydroquinone are currently made by the same type of chemistry used... 

Hocking, M.B. (1997) Vanillin synthetic flavoring from spent sulfite liquor, journal of Chemical Education... 

M.B. Hocking, Vanillin Synthetic Flavoring from Spent Sulfite Liquor. Chem. Educ. 74(9), 1055-1059 (1997). 

The group containing the vanillins synthetized form phenols via guaiacol is clearly split into three subgroups in the plane of the first two canonical functions (Fig. 3) but a careful examination of the upper cluster shows that three samples are situated above the D, D2 plane (z coordinate 4.35) and all the other samples lie below (z coordinate -1.45). 

The most important component of the vanilla bean, as far as flavour is concerned, is vanillin. Synthetic vanillin costs only a few pounds per kilogramme but vanillin extracted from vanilla beans can cost 5000 or more per kg. Food labelling laws are very strict and the penalties for declaring a flavour to be natural when it is not, are very high. Not only can companies be fined for false declaration but also their directors are liable to imprisonment in certain countries, in particular, in the United States. It is therefore very important that a company buying vanilla should be able to verify for itself whether or not the goods for sale are of natural origin. 

Vanillin was isolated for the first time from vaniUa pods by Nicolas-Theodore Gobley in 1858, and by 1874 its structure was elucidated by Ferdinand Tiemann and Wilhelm Haarmann. Because of its high price and a considerably variable product yield, dependent on weather conditions, there was a strong incentive to prepare vanillin synthetically. This was the time, when the scent and flavours industry was born. 

M. B. Hocking (1997) Vanillin synthetic flavoring from spent sulfite liquor. J. Chem. Educ., 74, 1055-1059. http //jchemed.chem.wisc.edu/Journal/Issues/1997/Sep/absl055.html (last access February 25,2014). 

VANILLIN In vanilla beans of course. But never more than 2%. This stuff is bought as a synthetic and is cheap and legal. 

Vanilla flavoring in bakery goods, confectionery, and many fro2en desserts need not be natural vanilla. The artificial and synthetic vanilla flavors that are used include vanillin [121-33-5] from lignin (wood pulp), ethyl vanillin [121 -32-4] and vanitrope [94-86-0], the latter two are synthetics. Over 90% of the U.S. market for vanilla flavor contains vanillin. These synthetics continue to dominate the market because of availabiUty, quahty, and relatively low and stable prices. 

Flavor-Masking Deodorant. In addition to its use as a constituent of perfume compositions, vanillin is also useful as a deodorant to mask the unpleasant odor of many manufactured goods. As a masking agent for numerous types of ill-smelling mass-produced industrial products, particularly those of synthetic mbber, plastics, fiber glass, inks, etc, vanillin finds extensive use. It is often the most inexpensive material for the amount of masking effect it provides. Only traces are required for this purpose as the odor of vanillin is perceptible in dilutions of 2 x 10 mg/m of air. Cmde vanillin is acceptable for such purposes. 

Vanillin, CgHgOj, is one of the most important synthetic perfumes. It is the active odorous ingredient of the vanilla pod, in which it occurs to the extent of about 2 per cent., appearing on the surface of the bean as a fine white crystalline efflorescence. It occurs naturally also in Sumatra benzoin (about 1 per cent.), Siam benzoin (15 per cent.), and the balsams of Tolu and Peru (traces). Numerous other bodies have been recorded as containing it, such as asafoetida, beetroot and asparagus, the seeds of Lupinus albus, the seeds of Sosa canina, etc. 

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. 

Ethyl vanillin is a synthetic compound that is three and a half times stronger in flavor than real vanilla, although the flavor is not quite the same. Because it is less expensive and keeps better during storage and transport, ethyl vanillin is used as a substitute for vanilla in foods and perfumes. 

Natural and artificial flavors are also added, usually in the form of vanilla extract or synthetic vanillin or ethyl vanillin. 

The opiate alkaloid, papaverine, from Papaver somniferum is an anti-spasmodic, vasodilator, and smooth muscle relaxant. Its total synthesis has been studied since Pictet and Gams early work in 1909 and has since been followed up by various industrial syntheses up till the early 1950s using important industrial commodities as vanillin, acetovanillone, veratraldehyde (methylvanillin), and homoveratric acid as starting materials (see Figure 4.50). Table 4.23 summarizes the results of the five synthetic plans for this natural product. All are convergent... 

Eugenol is a natural product available from a variety of essential oils (cinnamon-tree or pimentos leaves). Its isomerization (Eq. 49) into isoeugenol, the starting material for synthetic vanillin, is rather difficult and proceeds in modest yields under relatively harsh conditions. It can, however, be very efficiently prepared by use of 2.2 molar equivalents of base and catalytic (5 %) amounts of Aliquat in the absence of solvent. 

These are materials that are synthetic but are the same compound as is present in a natural flavouring material. From time to time it emerges that one substance produces a given flavour. Most chemists know that benzaldehyde has a smell of almonds. Some chemists know that hydrogen cyanide smells of bitter almonds. If a natural flavouring can be represented by a single substance and that substance can be synthesised then the flavour is likely to be available as a nature identical flavour. Vanilla flavour is a good example. Vanilla flavour can be all natural and derived from vanilla pods or nature identical or artificial. The nature identical product would be based on vanillin, which is in vanilla pods and has a flavour of vanilla. An artificial vanilla flavour would be ethyl vanillin, which is not present in vanilla pods but has a flavour two and a... 

The Norwegian company Borregaard makes vanillin by chemo-oxidation of cheap natural lignin. In view of the complexity of the lignin structure this is a remarkable achievement. This semi-synthetic vanillin is, however, not allowed to carry the qualification of natural . Borregaard is the only global producer of lignin-vanillin or wood-sourced vanillin , with a volume of about 2000 t a-1. They obtain 4 kg vanillin from one ton of wood. This vanillin is more expensive than synthetic vanillin, but the flavorist needs lower doses of the extra round flavor . 

The price of synthetic vanillin has dropped to about 10 kg-1 due to increased production in China, which is now the number one supplier. In view of the very large price difference, analytical methods (isotope analysis) have been developed to distinguish between natural and synthetic vanillin. 

The known hazardous effects of most synthetic corrosion inhibitors are the reasons for the search of safer and environmentally friendly natural products. Plant extracts are viewed as an incredibly rich source of naturally synthesized chemical compounds that can be extracted at low costs. Naturally occurring substances such as vanillin [1], Opuntia extracts [2], lawsonia extract [3], natural honey [4] and extracts of chamomile, halfabar, black cumin and kidney bean [5] are some... 

Essential oils are organic compounds derived from flowers, seeds, leaves, roots, resins, and citrus fruits. The structures of many fragrant compounds have been studied, and processes for making these valuable compounds in a laboratory have been developed. There are now approximately 5000 synthetically produced chemicals that are available to a perfumer. These chemicals include vanillin, rose oxides, and the damascenes, or rose ketones. 

Most of the vanillic acid was reduced by E. coli containing Car in 2 h to vanillin (80 %) and vanillyl alcohol (20 %). Car does not reduce aldehydes to alcohols. However, E. coli s endogenous aldehyde reductase/dehydrogenase reduces vanillin to vanillyl alcohol. The broad substrate specificity of Car enables the wide application of this biocatalyst to other important applications, such as enantiomeric resolution of isomers such as ibuprofen and the reductions of many other natural and synthetic carboxylic acids. 

Extracts of the male oil palm bunch moths, Tirathaba mundella Walker (Lepidoptera Pyralidae), were shown to contain four compounds namely, 5S, 65)-2,2,6-trimethyl-6-vinyl-tetrahydro-pyran-3-ol, 4-hydroxy-3-methoxy benzaldehyde (vanillin), 6,10,l4-trimethyl-2-pentadecanone, and the corresponding alcohol 6,10,l4-trimethyl-2-pentadecanol, which elicited responses from the females. However, when synthetic compounds were used in lures, the ketone and alcohol by themselves did not attract females, suggesting that they might not be an essential part of the blend. This can only be confirmed once their absolute configuration has been determined and the proper stereoisomers tested in the... 

Whereas natural vanilla flavor from beans (recognized by the black dots ), is used in premium ice creams, soft drinks are flavored with synthetic vanillin. Natural vanilla contains other flavoring agents as well. Thus, F F is the only segment of the chemical industry where impurities add to the quality—and the price—of a product ... 

Chemical substitution, where chemists devise synthetic routes to make commercial production of the chemical economical— vanillin is one example. 

Figure 4.1. The 2-D (left) and 3-D (right) structures of synthetic or naturally occurring vanillin, the chemical that gives vanilla extract its characteristic flavour and smell. Neither representation of the structure provides a guide to the fact that humans like its flavour or smell, or indeed that the human nose can specifically detect the molecule.

Figure 4.3. Using the example of one synthetic route to vanillin (see Figure 4.1), one problem of the lack of specificity of chemical reagents is revealed—two products, not one, are produced, if a long sequence of chemical reactions is needed to convert a cheap, readily available starting material into a valuable substance, the percentage of the desired intermediate gained at each stage is one of the major factors in judging the economic viability of the synthesis (another major factor is the cost of ridding the final desired product of the inevitable impurities produced by the side reactions).

In 1874, Holzminden chemists Ferdinand Tiemann and Wilhelm Haarmann first succeeded in synthesising vanillin from coniferin. Holzminden became the site where vanillin was first produced industrially. Haarmann Reimer was the world s first factory in which synthetic scents and flavourings were produced [5]. 

Synthetic vanillin is a major intermediate in the production of various chemicals, including medicines and herbicides. Because of the large difference in price between vanillin from a natural origin and synthetic vanillin, counterfeiting is not uncommon. As natural and synthetic vanillin are chemically identical, isotope ratios of hydrogen (D/ff) and carbon ( C/ C) isotopes are used to... 

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