Vanilin

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Vanilin kao sirovina za parfeme — Bazne note

Vanilla planifolia (natural source; most vanillin is synthetic)

Definicija

Vanillin is an aromatic aldehyde, 4-hydroxy-3-methoxybenzaldehyde. It is a white or slightly yellow crystalline solid with a sweet, creamy, vanilla odour.

SLADAK PUDERAST TOPAO KREMAST BALZAMSKI

4-hydroxy-3-methoxybenzaldehyde, methyl vanillin, vanillic aldehyde

Type: Sirovina
Olfactive family: Gurmanski
Source: synthetic, mainly from petrochemical guaiacol and also from lignin; natural in cured vanilla pods
Chemical class: aromatic aldehyde

Instrumenti

Piramida

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BBazne note

Zemlje proizvođači

Natural vanillin: Indonesia, Madagascar, China, Guadeloupe, wood-based vanillin: Norway

Miris

Vanillin smells of vanilla: sweet, balsamic and pleasant. Its odor is also described as sweet and creamy, and as a pleasant aromatic vanilla odor. Another description gives a sweetish smell. In water, its odor is detected at 0.200 ppm and recognised at 4.00 ppm.

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Detaljno

Identity and properties

Vanillin is 4-hydroxy-3-methoxybenzaldehyde, with CAS number 121-33-5. Its formula is C₈H₈O₃ and its molecular weight is 152.15. The molecule has two functional groups, the phenolic OH and the aldehyde. Its taste is a pleasant vanilla.

Vanillin crystallizes in a monoclinic structure. It is very soluble in ethanol, diethyl ether and acetone, and soluble in benzene and ligroin. It oxidizes slowly and somewhat on exposure to moist air, and light affects it. Alkalies decompose it.

Occurrence

Cured vanilla pods contain about 2% vanillin by dry weight. Real vanilla extract from the seedpod is a complex mixture of several hundred compounds, including vanillin, acetaldehyde, acetic acid, furfural, hexanoic acid, 4-hydroxybenzaldehyde, eugenol, methyl cinnamate and isobutyric acid. Synthetic vanilla essence is a solution of synthetic vanillin in ethanol. Vanillin is also found in Leptotes bicolor, an orchid native to Paraguay and southern Brazil. At lower concentrations, vanillin also contributes to the flavor and aroma of foods as varied as olive oil, butter, raspberry and lychee. Of the vanilla species, only three are relevant as sources of vanillin: Vanilla planifolia, Vanilla pompona and Vanilla tahitensis.

Market and uses

Synthetic vanillin accounts for 88% of the global market, natural vanillin from pods for only 1.5%, and plant-based vanillin for 11.5%. In 2001 the annual demand for vanillin was 12,000 tons, but only 1,800 tons of natural vanillin were produced. Synthetic vanillin sells for around 10-20 USD/kg. Natural vanillin costs from a minimum of USD 1250/kg to 4400/kg.

Vanillin has antimicrobial properties and acts synergistically with conventional preservatives. Its phenolic OH and aldehyde groups may act as handles for chemical reactions, so vanillin can take part in polymerisation reactions that yield bio-based polymers and resins. Vanillin may also be a starting molecule for specialised molecules, among them capsaicin and piperonal (heliotropine).

Labelling in the EU

In July 2023 the European Commission published Regulation 2023/1545, which amends the EU Cosmetics Regulation 1223/2009 and adds fragrance allergens, vanillin among them, that were previously not subject to individual labeling. In the EU, these allergens must be named in the ingredient list when present above 0.01% in a rinse-off cosmetic and above 0.001% in a leave-on cosmetic.

Ethyl vanillin

Ethyl vanillin is 3-ethoxy-4-hydroxybenzaldehyde, CAS 121-32-4. It is a homologue of vanillin that carries an ethoxy group on the 3 position where vanillin has a methoxy group. As a flavorant, ethyl vanillin is about three times as potent as vanillin and is used in the production of chocolate. Its aroma is described as sweet, creamy, vanilla, caramellic and root beer.

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Istorija

Théodore Nicolas Gobley first isolated vanillin as a relatively pure substance in 1858, by evaporating a vanilla extract to dryness and recrystallizing the solids from hot water. In 1874 the German scientists Ferdinand Tiemann and Wilhelm Haarmann deduced its chemical structure and at the same time found a synthesis for vanillin from coniferin, a glucoside of coniferyl alcohol found in pine bark. In 1876 Karl Reimer synthesized vanillin from guaiacol.

Semisynthetic vanillin made from the eugenol of clove oil was commercially available by the late 19th century, and vanillin was commercially produced from eugenol until the 1920s. Synthetic vanillin became significantly more available in the 1930s, when production from clove oil was supplanted by production from the lignin-containing waste of sulfite pulping. By 1981, a single pulp and paper mill in Thorold, Ontario, supplied 60% of the world market for synthetic vanillin. At one producer, vanillin production from lignin derived from Norway spruce began in 1962.

The two-step process from guaiacol and glyoxylic acid has been practiced since the 1970s. From 2000, a biosynthetic vanillin made by microorganisms acting on ferulic acid extracted from rice bran was marketed.

Zanimljivosti

Relatively pure vanillin may be visible as a white dust or "frost" on the outside of cured pods of high quality. Green vanilla pods contain vanillin only in its glucoside form and lack the characteristic odor of vanilla. Vanillin made by microorganisms from rice-bran ferulic acid was sold at USD 700/kg, against about US$15/kg for petrochemical vanillin, yet it could be labeled as a natural flavoring, which vanillin from lignin or guaiacol cannot. Wild vanilla orchids have only a 1% chance of successful pollination, so all vanilla grown today is pollinated by hand.

Dobijanje i hemija

Način dobijanja

Approximately 85% of the world's vanillin is synthesized in a two-step process from the petrochemical precursors guaiacol and glyoxylic acid, and approximately 15% is still made from lignin wastes. In the guaiacol route, guaiacol reacts with glyoxylic acid by electrophilic aromatic substitution, and the resulting vanillylmandelic acid is converted through 4-hydroxy-3-methoxyphenylglyoxylic acid to vanillin by oxidative decarboxylation. The condensation is highly regio-selective towards the para position, which avoids side products. Although guaiacol can be obtained by pyrolysis of wood, the type intended for vanillin production is mainly produced by petrochemistry. The crude vanillin can then be purified with vacuum distillation and recrystallization. A third route transforms guaiacol in two steps with HCHO and O2, first into vanillyl alcohol and then into vanillin. Another synthetic method isomerizes eugenol to isoeugenol with KOH in diethylene glycol, protects the OH as an acetate and oxidizes it to vanillin. Wood-based vanillin is produced from lignosulfonates, a byproduct of making cellulose by the sulfite process. The lignin process is no longer popular because of environmental concerns. Today a single manufacturer remains for vanillin made from lignin. Natural vanillin is recovered from the pod of a tropical orchid, especially Vanilla planifolia. In the green bean, vanillin is present as vanillin glucoside, which is hydrolyzed by enzymes into vanillin and glucose during curing. Plant-based vanillin is obtained biotechnologically by enzymatic or microbial transformation of non-oil-based precursors such as ferulic acid, eugenol or glucose.

Formula: C₈H₈O₃
CAS: 121-33-5
Botanički naziv: Vanilla planifolia (natural source; most vanillin is synthetic)
Izgled: white or off-white crystalline powder
Sinonimi: 4-hydroxy-3-methoxybenzaldehyde, methyl vanillin, vanillic aldehyde

Status prema standardima IFRA

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No IFRA Standard for the material itself (51st Amendment)

Fizička svojstva

Tačka ključanja: 285.00 to 286.00 °C. @ 760.00 mm Hg
Tačka topljenja: 81-83 °C
Tačka paljenja: 153 °C (307 °F), closed cup

U parfemima

Vanillin is the principal flavor and aroma compound in vanilla. Synthetic vanillin is sold mainly to ice-cream and chocolate manufacturers, and in the form of fragrances to flavor companies. Natural vanillin recovered from vanilla pods can be used without restriction for edible and pharmaceutical purposes and can be labelled as natural vanilla flavor.

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