Vanillin is an organic compound with the molecular formula C8H8O3. It is a phenolic aldehyde. Its functional groups include aldehyde, hydroxyl, and ether. It is the primary component of the extract of the vanilla bean. Synthetic vanillin is now used more often than natural vanilla extract as a flavoring agent in foods, beverages, and pharmaceuticals.
Vanillin and ethylvanillin are used by the food industry; ethylvanillin is more expensive, but has a stronger note. It differs from vanillin by having an ethoxy group (−O−CH2CH3) instead of a methoxy group (−O−CH3).
Natural vanilla extract is a mixture of several hundred different compounds in addition to vanillin. Artificial vanilla flavoring is often a solution of pure vanillin, usually of synthetic origin. Because of the scarcity and expense of natural vanilla extract, synthetic preparation of its predominant component has long been of interest. The first commercial synthesis of vanillin began with the more readily available natural compound eugenol (4-allyl-2-methoxyphenol). Today, artificial vanillin is made either from guaiacol or lignin.
Vanillin crystals extracted from vanilla extract
Lignin-based artificial vanilla flavoring is alleged to have a richer flavor profile than oil-based flavoring; the difference is due to the presence of acetovanillone, a minor component in the lignin-derived product that is not found in vanillin synthesized from guaiacol.
Vanilla was cultivated as a flavoring by pre-Columbian Mesoamerican people; at the time of their conquest by Hernán Cortés, the Aztecs used it as a flavoring for chocolate.
Vanillin was first isolated as a relatively pure substance in 1858 by Nicolas-Theodore Gobley, who obtained it by evaporating a vanilla extract to dryness and recrystallizing the resulting solids from hot water. In 1874, the German scientists Ferdinand Tiemann and Wilhelm Haarmann deduced its chemical structure, at the same time finding a synthesis for vanillin from coniferin, a glucoside of isoeugenol found in pine bark.
Tiemann and Haarmann founded a company Haarmann and Reimer (now part of Symrise) and started the first industrial production of vanillin using their process in Holzminden, Germany. In 1876, Karl Reimer synthesized vanillin (2) from guaiacol (1).
By the late 19th century, semisynthetic vanillin derived from the eugenol found in clove oil was commercially available.
Synthetic vanillin became significantly more available in the 1930s, when production from clove oil was supplanted by production from the lignin-containing waste produced by the sulfite pulping process for preparing wood pulp for the paper industry. By 1981, a single pulp and paper mill in Thorold, Ontario supplied 60% of the world market for synthetic vanillin.
However, subsequent developments in the wood pulp industry have made its lignin wastes less attractive as a raw material for vanillin synthesis. Today, approximately 15% of the world’s production of vanillin is still made from lignin wastes, while approximately 85% synthesized in a two-step process from the petrochemical precursors guaiacol and glyoxylic acid.
Beginning in 2000, Rhodia began marketing biosynthetic vanillin prepared by the action of microorganisms on ferulic acid extracted from rice bran. At 700 USD/kg, this product, sold under the trademarked name Rhovanil Natural, is not cost-competitive with petrochemical vanillin, which sells for around US$15/kg. However, unlike vanillin synthesized from lignin or guaiacol, it can be labeled as a natural flavoring.
Vanillin is the main chemical compound of the extract of the vanilla bean. Nowadays, vanillin is mainly used as a flavouring agent, usually in sweet foods such as ice cream and chocolate. Did you know that 99% of the vanillin today does not come from the vanilla beans but is produced synthetically?
It can be produced in different ways: from a petrochemical raw material called guaiacol, from wood, or from other biomass sources (organic material coming from plants). Today, 15% of the world’s production of vanillin comes from lignin (see our previous article on lignin), mainly by the Norwegian company Borregaard.
As the extraction of vanillin from biomass sources is one of the objectives of the Liberate project, let’s have closer look at this process. It all starts with the wood that is used to produce paper by extracting its cellulose. After extracting the cellulose, what is left is mostly Kraft lignin that, until recently, had little commercial value.
Now, thanks to a complex oxidation process of the lignin structures, it is possible to extract vanillin from this lignin. The main advantage claimed by its producers is its much lower carbon footprint compared to its petrochemical counterparts.
Within the Liberate project, vanillin is obtained through an electro-chemical and thermal depolymerization process that oxidizes and breaks the lignin into small molecules. The objective is to extract 7% of the vanillin contained in the lignin, compared to a 2% efficiency yield with commercial technologies currently available. This major improvement will lower the production costs and open new doors for applications where vanillin is used as a raw material.
And as a last point, do you know why old books have this special smell? Because the paper is made from cellulose, which also contains some vanillin, present as a residue.
But vanillin kills microorganisms!
However, it’s not a straight forward road. For one thing, vanillin is an antimicrobial. It’s made by plants to combat microorganisms. As such, it can actually be toxic to microorganisms!
Also, the yield, so the amount of material made in a batch, of these methods is generally quite low. Large vessels of microorganisms are necessary to produce just minor amounts of vanillin.
Converting ferulic acid using yeast
Nevertheless, progress is being made. Researchers have found a way to use yeast to convert ferulic acid, again a lookalike of vanillin, into vanillin. Unfortunately, ferulic acid is also expensive, driving up costs.
Bacteria can convert eugenol
Whereas we can use chemicals to convert eugenol into vanillin, it might also be possible to use bacteria. These bacteria do the same as the chemical process does, but generally in a less harsh way.
Make vanillin from plastic
Last but not least, scientists have recently (2021) found a way to use bacteria (E. coli) to convert plastic into vanillin! PET plastic can be broken down into terephthalic acid and some other molecules. The bacteria can transform this acid into vanillin.
It’s not a fully operational technology just yet, but, it comes to show, that we humans remain inventive. We want our vanilla flavored ice cream, and ever since the 19th century have come up with new ways to do so!
Where does most vanillin come from?
According to research, the primary sources for vanillin are lignin, eugenol and guaiacol. This is the main reason why the production of vanillin has been decreasing for the past 30 years.
Vanillin synthesis from lignin waste – Borregaard
Vanillin production from lignin – Borregaard
FSC® Certified wood products come from certified forests that meet strict environmental, social, and governance standards. They are also different in their “chemical composition”, particularly in regard to potentially toxic substances such as dioxins and furans.
How do you get vanillin?
Synthesizing vanillin from molasses
The patent for converting lignin into vanillin was filed by the Norwegian company Borregaard in 1961. Until then, the substance had been extracted from either eugenol or guaiacol. These chemicals have an aspect of “harmful” and are actually toxic, so it is necessary to find alternatives.
The process is complex but very simple at the same time. And what’s more, it’s natural ! It involves aqueous oxidation and reduction of lignin (naturally present in wood) to produce vanillin (see box).
Borregaard is the only company producing vanillin in the world. It is a medium-sized international player, with annual revenues of approximately EUR 1 billion. It operates on four continents, with a significant presence in India and Brazil. Borregaard is a pioneer in industrial biotechnology having introduced one of the world’s first industrial biocatalysts in 1989 and has been producing vanillin from lignin for almost 50 years.
What’s so special about Borregaard? The company is located in Norway where wood is abundant but also expensive to extract. Thus, another value added activity was conceived: turning this wood into something that could be sold on the market.
How is natural vanillin produced?
The industrial process of “industrial biotechnology” (Naturstoff, Naturprodukt) is a biological treatment of lignin to convert it into vanillin. The lignin is first extracted from wood in the paper production, but there is a lot left over. In fact, 50% of the wood is lignin.
When we burn paper in biomass plants or when we heat it to make pulp for cardboard, the lignin is released into the air as a gas (see our article on biofuels). This gas can be captured and purified in several ways that are described.
What is the difference between vanillin and vanilla?
Vanilla is the taste of a fruit that only grows in the tropics. It is usually picked from the vanilla orchid (Vanilla planifolia) and then processed into extract which is often used for baking.
The essence or extract is the oven: it gives its flavor to food. The difference between vanillin and vanilla extract lies in the amount of vanillin contained in it. Vanilla extract is composed of 60% alcohol and many other ingredients, while vanillin is pure.
Natural vanillin production process
The lignin is a byproduct of the paper industry. It can be used to produce vanillin and at the same time reduce CO 2 emissions. The main raw material for preparing vanillin from lignin is biomass, which can itself be renewable (when it comes from trees).
The procedure is quite simple: the lignin in wood produces water-soluble organic acids (malic, acetic) that will oxidize if oxidizing bacteria are added.
What is ethyl vanillin made from?
This process was patented by Borregaard in 1965 and produced by them ever since. The company has introduced new technologies that have made the production of vanillin more cost-effective, including the use of renewable raw materials and biological processes.
Vanillin is a semi-volatile organic compound that occurs in many plants, and it is formed from the breakdown of ethyl guaiacol by hydrogen peroxide (H 2 O 2 ).
Vanillin naturally occurs in many different foods and has been used as a flavouring agent for many years (16th century), especially in sweetened beverages such as soda water. It is also used as a food additive to replace natural vanilla flavour.
Is vanillin bad for your health?
Vanillin is a natural substance produced by plants. It is also used as a food additive and flavouring agent.
It has been studied for many years, but it might also be harmful for your health?
Vanillin does not seem to be more harmful than other artificial flavouring agents. However, it is not known whether vanillin would affect the human system differently to the other colours because of its nature as a semi-volatile organic compound, or even if vanillin would not have any effect at all. Most of the research on vanillin has only focused on its toxicity rather than on its effects in the human body over time.
Ethyl vanillin is found in the leaves of the vanilla (Vanilla planifolia) fruit, from which it can be extracted and purified. It can also be synthesised from lignin (Borregaard) and has been used in the food industry for many years. It is one of the main components in eau de parfum with a floral note.
Cocoa flavanols and natural vanilla flavour as a whole have a great potential for human consumption for their beneficial effects on health. However, further research is necessary to ensure that there are no harmful effects on health caused by different concentrations of vanillin before considering its addition to food.
Vanillin can be produced from lignin, a byproduct of the paper industry. It has been studied for many years, but it could also be harmful for your health. Therefore, further research is needed to ensure that there are no harmful effects on health caused by different concentrations of vanillin before considering its addition to the food supply.
Many natural foods contain vanillin such as vanilla extracts and cocoa beans. Vanilla extract is composed of 60% alcohol and many other ingredients, while vanillin is pure.