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Introduction

Historical

Preparation

Characterisation

Spice

Medicine

 Phytochemistry

 References  

Historical

Zingerone has been extracted from ginger for the past two thousand years.

A Brief History

Common Name:
Ginger
Latin Name: Zingiber Officinale
Family: zingiberaceae
Other Names: Based on its origin:

African ginger

Black ginger

Chochin (Asian ginger).

Gan Jiang (Jamaican ginger).

The word ginger comes from the ancient Sanskrit 'singabera', meaning 'shaped like a horn'.  It first appeared in the writings of Confucius in the 5th century BC. and it has been used medicinally in the West for the past 2000 years. Various virtues have been ascribed to the spice; e.g. Henry VIII recommended it as a pro-phylactic against the plague. It was introduced by the Spaniards to the Americas and is now cultivated extensively in the West Indies. The Portuguese introduced it to West Africa. It is now used all over the world.

Only in the past century has zingerone been produced synthetically. A few interesting and unique syntheses have been chosen. Down the years, the technique of synthesis evolved. Though Lapworth & Wykes were the pioneers in the synthesis of zingerone, their method and reagents were not repeated. Below is a diagram of the apparatus used in their experiment.

Nomura, then Mannich and Merz founded the method used today. This is shown by Kim and Kim's work. The other interesting method was formed by Bunce and Reeves. This method and the common one used today are elaborated on in the preparation section.

Year

Method Reagents
1917 Reduction and Decarboxylation of ethyl vanillylideneacetoacetate 

Lapworth & Wykes

 

The Pioneers in the synthesis.

Na Amalgam and NaOH solution

 

1925 Reduction of 4-(4-hydroxy-3-methoxyphenyl)buten-2-one to 4-(4-hydroxy-3-methoxyphenyl)butan-2-one.

Nomura

 

Na Amalgam and Water

 

1927  

Reduction of 4-(4-hydroxy-3-methoxyphenyl)buten-2-one to 4-(4-hydroxy-3-methoxyphenyl)butan-2-one.

Mannich & Merz

 

Pd Catalyst,

 

1979  

Reaction of 4-benzyloxy-3-methoxybromomethylbenzene with the anion of acetone dimethylhydrazone, followed by oxidative hydrolysis, then hydrogenolysis to remove the benzyl group

 

Enders D. et Al

 

Pd/C, Hydrogen, Methanol

 

1989 Amberlyst-15-catalyzed addition of 3-buten-2-one to the phenol

Bunce & Reeves

 

Amberlyst-15, Toluene, 20-50°C

 

2004  

Reduction of 4-(4-hydroxy-3-methoxyphenyl)buten-2-one to 4-(4-hydroxy-3-methoxyphenyl)butan-2-one.

Kim D. & Kim J. Y.

 

Pd/C Catalyst,

 

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