Zingerone
Encyclopedia
Zingerone, also called vanillylacetone, is a key component of the pungency of ginger. Zingerone is a crystalline solid that is sparingly soluble in water, but soluble in ether.
Zingerone is similar in chemical structure to other flavor chemicals such as vanillin
and eugenol
. It is used as a flavor additive in spice oils and in perfumery to introduce spicy aromas.
Fresh ginger does not contain zingerone; cooking the ginger transforms gingerol
, which is present, into zingerone through a retro-aldol reaction (reversal of aldol addition).
Ginger compounds have been shown to be active against enterotoxigenic
Escherichia coli
heat-labile enterotoxin-induced diarrhea . This type of diarrhea is the leading cause of infant death in developing countries. Zingerone is likely the active constituent responsible for the antidiarrheal efficacy of ginger.
Zingerone is similar in chemical structure to other flavor chemicals such as vanillin
Vanillin
Vanillin is a phenolic aldehyde, an organic compound with the molecular formula C8H8O3. Its functional groups include aldehyde, ether, and phenol. It is the primary component of the extract of the vanilla bean. It is also found in Leptotes bicolor, roasted coffee and the Chinese red pine...
and eugenol
Eugenol
Eugenol is a phenylpropene, an allyl chain-substituted guaiacol. Eugenol is a member of the phenylpropanoids class of chemical compounds. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, basil and bay leaf. It is slightly...
. It is used as a flavor additive in spice oils and in perfumery to introduce spicy aromas.
Fresh ginger does not contain zingerone; cooking the ginger transforms gingerol
Gingerol
Gingerol, or sometimes [6]-gingerol, is the active constituent of fresh ginger. Chemically, gingerol is a relative of capsaicin and piperine, the compounds which give chilli peppers and black pepper their respective spicyness...
, which is present, into zingerone through a retro-aldol reaction (reversal of aldol addition).
Ginger compounds have been shown to be active against enterotoxigenic
Enterotoxin
An enterotoxin is a protein toxin released by a microorganism in the intestine. Enterotoxins are chromosomally encoded exotoxins that are produced and secreted from several bacterial organisms. They are often heat-stable, and are of low molecular weight and water-soluble...
Escherichia coli
Escherichia coli
Escherichia coli is a Gram-negative, rod-shaped bacterium that is commonly found in the lower intestine of warm-blooded organisms . Most E. coli strains are harmless, but some serotypes can cause serious food poisoning in humans, and are occasionally responsible for product recalls...
heat-labile enterotoxin-induced diarrhea . This type of diarrhea is the leading cause of infant death in developing countries. Zingerone is likely the active constituent responsible for the antidiarrheal efficacy of ginger.