Vanillin ethyl

Bourbonal ethylprotal ethylprotocatechuic aldehyde 4-hydroxy-3-ethoxybenzaldehyde Rhodiarome vanillal. 

Ethyl vanillin is used as an alternative to vanillin, i.e., as a flavoring agent in foods, beverages, confectionery, and pharmaceuticals. It is also used in perfumery. 

Ethyl vanillin possesses a flavor and odor approximately three times as intense as vanillin, hence the quantity of material necessary to produce an equivalent vanilla flavor may be reduced, causing less discoloration to a formulation and potential savings in material costs. However, exceeding certain concentration limits may impart an unpleasant, slightly bitter taste to a product due to the intensity of the ethyl vanillin flavor. See Table I. 

White or slightly yellowish crystals with a characteristic intense vanilla odor and flavor. 

Flash point 127°C Melting point 76-78°C Solubility see Table III.  

---

The FCC is to food-additive chemicals what the USP—NF is to dmgs. In fact, many chemicals that are used in dmgs also are food additives (qv) and thus may have monographs in both the USP—NF and in the FCC. Examples of food-additive chemicals are ascorbic acid [50-81-7] (see Vitamins), butylated hydroxytoluene [128-37-0] (BHT) (see Antioxidants), calcium chloride [10043-52-4] (see Calcium compounds), ethyl vanillin [121-32-4] (see Vanillin), ferrous fumarate [7705-12-6] and ferrous sulfate [7720-78-7] (see Iron compounds), niacin [59-67-6] sodium chloride [7647-14-5] sodium hydroxide [1310-73-2] (see lkaliand cm ORiNE products), sodium phosphate dibasic [7558-79-4] (see Phosphoric acids and phosphates), spearmint oil [8008-79-5] (see Oils, essential), tartaric acid [133-37-9] (see Hydroxy dicarboxylic acids), tragacanth [9000-65-1] (see Gums), and vitamin A [11103-57-4]. 

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. 

Methyl vanillin is used in flavorings, fragrances, pharmaceuticals, and perfumes. It is closely related to ethyl vanillin, a slightly larger molecule. 

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. 

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... 

It remains an interesting speculation what would happen if a mutation of vanilla was produced that produced ethyl vanillin rather than vanillin. The new variety would be much more potent as a flavour. However, ethyl vanillin might then have to be classified as nature identical. 

Ethyl toluates, e204, e205, e206 Ethyl p-tolyl ether, m3 7 3 Ethyl trimethylacetate, el28 Ethyl vanillin, e46 Ethyne, a41 Ethynylbenzene, p84... 

In most European countries, flavors that occur naturally or are generated during healing or processing by enzymatic reactions or modification generally arc considered natural flavors. Flavors that arc often referred to in the United Stales as synthetic are usually termed "artificial" in Europe. These would include such compounds as ethyl vanillin, allyl-of-iononc, and ethyl maltol. However, substances that are synthesized but chemically identical to the naturally occurring substances arc classified as "natural-identical." This class would include diacetyl, benzaldehyde, antsyl acetate, and benzophenone. 

SYNTHESIS A solution of 83 g bourbonal (also called ethyl vanillin, or vanillal, or simply 3-ethoxy-4-hydroxybenzaldehyde) in 500 mL MeOH was treated with a solution of 31.5 g KOH pellets (85% material) dissolved in 250 mL H,0. There was then added 71 g methyl iodide, and the mixture was held under reflux conditions for 3 h. All was added to 3 volumes of H20, and this was made basic with the addition... 

Ethyl trimethylacetate, el23 Ethyl vanillin, e39 Ethyne, a41 Ethynylbenzene, p82... 

A basic white cake was chosen as a model system for the study because of its relative simplicity. Ethyl vanillin was added as a marker conpound which was traced throughout the analyses. The formulation (1) was as follows ... 

Although the aliphatic aldehydes had been used in a number of earlier perfumes, their dominance (a total of nearly 1%) in Chanel No. 5 marked a milestone in the history of perfumery, and the combination of materials that make up the central accord of the perfume remains one of the most unmistakable, being used also for the perfuming of many types of functional products, from toiletries to room fresheners, where the relative chemical instability of the vanillin (or ethyl vanillin) and the aliphatic aldehydes does not present too much of a problem. 

At the time when Shalimar was made it was customary to use a high proportion of the alcoholic tinctures made from natural products, rather than the concentrated absolutes and resins. These would have included such products as vanilla, benzoin, and tonka to give naturalness to the ethyl vanillin and coumarin, as well as tinctures of civet, castoreum, ambergris, and musk. Such products retain more of the most volatile components of the starting material, giving a wonderful quality and life to the finished product. 

---