Vanillin
Vanillin is the heads flavour material of the vanilla and an nature-identical flavour material. In the year 1874 Dr. succeeded to the chemist. William hair man as well as Ferdinand Tiemann in Holzminden the synthesis of Vanillin from the crust juice of spruces.
| Structural formula | |||
|---|---|---|---|
| |||
| general | |||
| Name | Vanillin | ||
| other names | 4-Hydroxy-3-methoxy-benzaldehyd | ||
| sum formula | C 8 H 8 O 3 | ||
| CAS number | 121-33-5 | ||
| short description | white solid | ||
| characteristics | |||
| mol mass | 152.15 g mol | ||
| state of aggregation | firmly | ||
| density | 1.056 g/cm ³ | ||
| melting point | 82-83 °C | ||
| boiling point | 285 °C | ||
| steam pressure | ? Pa (x °C) | ||
| solubility | well in ethanol, Ether, chloroform, carbon disulfide, acetic acid, badly in water (10 g/L with 20 °C) | ||
| of safety references | |||
| of Gefahrensymbole | |||
| |||
| R and S-sentences |
of R: 22 | ||
| MAK | ? | ||
| As far as possible and common, SI-UNITs are used.If not differently notes, the indicated data apply with standard conditions. | |||
To table of contents |
occurrences
Vanillin is at the most frequent in the Schoten of the spice vanilla (Vanilla planifolia) (1,5 4%) furthermore also in Styrax, spice carnations and other plants.
synthesis
Vanillin can be won technically by oxidation of Eugenol with potassium permanganate or ozone. Guajacol leaves itself with formaldehyde and nitrobenzene sulfone acid in oneseveral days continuing process to Vanillin and Metanilsäure convert. A further possibility is the condensation of the 4-Hydroxy-3-methoxymandelsäure formed by Guajacol with Glyoxylsäure and oxidation to Phenylglyoxylsäure, which is decarboxyliert to Vanillin .
A majority of the Vanillins becomes fromthe paper trade resulting sulfite wastes won. The lignin sulfone acid contained herein is treated at increased temperature and increased pressure with Oxidantien and alkalis, whereby among other things Vanillin develops, which is cleaned by extraction , distillation and crystallization.
Alternatively also biotechnological methods standfor the order. Vanillin can be made for example by Amycolatopsis or Streptomyces trunks of Ferulasäure. The Ferulasäure can be made likewise biotechnologically of Eugenol (Pseudomonas trunks; Fed batch procedure, there Eugenol toxically for the cell). Eugenol is a well available raw material and originates from carnation oil.Contrary to the chemical production (“nature-identically”) the biotechnologically manufactured Vanillin may be defined as “naturally”.
See also: Coniferin
reaction behavior
due to its bifunktionalen character is Vanillin very reaction-joyfully. Are by Veretherung , Veresterung or aldol condensation a great many derivativessynthesizable. By attack at the aromatic ring further reactions are possible.
use
Vanillin is sold for example as admixture to sugar (“Vanillinzucker”) and used as flavour material in food, among other things in ice-cream, baking goods and chocolate. Besides Vanillin is one of many odoriferous substances during the perfume production, where he is used in small quantities for the rounding and adjustment of sweet, balsamischen smells. Also in the chemical industry Vanillin is used, for example as basic material for productionof medicines. Vanillin is quantitatively the most important taste material world-wide, since he can be manufactured low-priced. One proceeds from a use of 12.000 tons in the year. Those about 2,000 tons of Schoten of genuine vanilla, which are harvested annually world-wide,contained only about 40 tons of Vanillin.
Today as artificial flavour material in place of the more expensive Vanillins the tasting 2-4 times more intensive synthetic Ethylvanillin is often used. Chemically Ethylvanillin develops, if one exchanges the group of methyls of the Vanillins against a group of ethyls (4-Hydroxy-3-ethoxy-benzaldehyd). As more naturalFlavour material seems to Ethylvanillin in the Barrique, i.e. in new Holzfässern removed red wines.
