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Eugenol is hepatotoxic, meaning it may cause damage to the liver

By the late 19th century, semisynthetic vanillin derived from the eugenol found in clove oil was commercially available

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vanillin 121-33-5 - The Good Scents Company

It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from phenol or from lignin.; It is one of many compounds that is attractive to males of various species of orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study.

it was developed a process of synthetic vanillin production from eugenol ..

The demand for vanilla flavoring has long exceeded the supply of vanilla beans. As of 2001, the annual demand for vanillin was 12,000 tons, but only 1,800 tons of natural vanillin were . The remainder was produced by chemical synthesis. Vanillin was first synthesized from eugenol (found in oil of clove) in 1874–75, less than 20 years after it was first identified and isolated. Vanillin was commercially produced from eugenol until the 1920s. Later it was synthesized from lignin-containing "brown liquor", a byproduct of the sulfite process for making wood pulp. Counter-intuitively, even though it uses waste materials, the lignin process is no longer popular because of environmental concerns, and today most vanillin is produced from the petrochemical raw material . Several routes exist for synthesizing vanillin from guaiacol.

PDF Downloads : Oriental Journal of Chemistry

English: synthesis of vanillin (former large-scale industrial): eugenol (1) -> isoeugenol (2) -> vanillin (3)

As far as large-scale industrial syntheses go, a classic early method starts from eugenol, which occurs naturally in cloves, nutmeg and cinnamon. This isomerises to isoeugenol in alkaline solution, and this in turn can be oxidised (by nitrobenzene) to vanillin.

This extraction can be done by the traditional acidification/precipitation followed by separation
Extraction of synthetic vanillin from Eugenol was the main route for more than 40 years, until it was discovered that vanillin could be produced from lignin present in the waste liquor of pulp and paper industry
Lignin based Synthetic Vanillin
After obtaining purified lignin, the Processing of synthetic vanillin is based on three main steps The first step consists of the alkaline lignin oxidation in a bubble column reactor,

Then, the mixture obtained in the reaction passes through a membrane ultra filtration process where the bigger molecules of degraded lignin are retained.

Toronto Research Chemicals - TRC Canada

The first commercial synthesis of vanillin began with the more readily available natural compound euge Express yourself

Vincent Caruso, Quynh Do, Kilsun Kim
Portland Community College
May 4-18, 2015

Leptotes bicolor
Vanilla planifolia
Can be synthesized from...
Pinus tabuliformis

The first commercial synthesis of natural Vanillin is synthesized from natural compound called Eugenol which is found in Clove oil and waste Lignin material.
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  • Phase I Detoxification Pathways

    The first commercial synthesis of vanillin began with the more readily available natural compound eugenol

  • The Preparation of Vanillin from Eugenol and Sawdust …

    Different Synthetic procedure of vanillin: Synthesis of Vanillin by eugenol Karl Reimer et al synthesized ..

  • Describes two procedures for the conversion of eugenol to vanillin

    The Multiple Faces of Eugenol

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