Vanillic acid (4-hydroxy-3-methoxybenzoic acid) is a

dihydroxybenzoic acid Dihydroxybenzoic acids (DHBA) are a type of phenolic acids. There are six main compounds, having all the same molecular formula C7H6O4. Those are: * 2,3-Dihydroxybenzoic acid (2-Pyrocatechuic acid or hypogallic acid) * 2,4-Dihydroxybenzoic acid ...

derivative used as a flavoring agent. It is an

oxidized Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a ...

form of

vanillin Vanillin is an organic compound with the molecular formula . 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 u ...

. It is also an intermediate in the production of vanillin from

ferulic acid Ferulic acid is a hydroxycinnamic acid, an organic compound with the formula (CH3O)HOC6H3CH=CHCO2H. The name is derived from the genus ''Ferula'', referring to the giant fennel ('' Ferula communis''). Classified as a phenolic phytochemical, ferul ...

Occurrence in nature

The highest amount of vanillic acid in plants known so far is found in the root of ''

Angelica sinensis ''Angelica sinensis'', commonly known as ''dong quai'' () or female ginseng, is a herb belonging to the family Apiaceae, indigenous to China. ''Angelica sinensis'' grows in cool high altitude mountains in East Asia. The yellowish brown root of th ...

'', an herb indigenous to China, which is used in

traditional Chinese medicine Traditional Chinese medicine (TCM) is an alternative medical practice drawn from traditional medicine in China. It has been described as "fraught with pseudoscience", with the majority of its treatments having no logical mechanism of acti ...

Occurrences in food

Açaí oil, obtained from the fruit of the açaí palm (''

Euterpe oleracea Euterpe (; el, Εὐτέρπη, lit=rejoicing well' or 'delight , from grc, εὖ, eû, well + el, τέρπειν, térpein, to please) was one of the Muses in Greek mythology, presiding over music. In late Classical times, she was named muse ...

''), is rich in vanillic acid (). It is one of the main natural phenols in

argan oil Argan oil is a plant oil produced from the kernels of the argan tree ('' Argania spinosa'' L.), which is indigenous to Morocco. In Morocco, argan oil is used to dip bread in at breakfast or to drizzle on couscous or pasta. It is also used for cos ...

. It is also found in

wine Wine is an alcoholic drink typically made from Fermentation in winemaking, fermented grapes. Yeast in winemaking, Yeast consumes the sugar in the grapes and converts it to ethanol and carbon dioxide, releasing heat in the process. Different ...

and

vinegar Vinegar is an aqueous solution of acetic acid and trace compounds that may include flavorings. Vinegar typically contains 5–8% acetic acid by volume. Usually, the acetic acid is produced by a double fermentation, converting simple sugars to eth ...

Metabolism

Vanillic acid is one of the main catechins

metabolite In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, ...

s found in humans after consumption of

green tea Green tea is a type of tea that is made from '' Camellia sinensis'' leaves and buds that have not undergone the same withering and oxidation process which is used to make oolong teas and black teas. Green tea originated in China, and since th ...

infusions.

Synthesis

Oxidation of

to the carboxylic acid occurred in ~88% yield.

References

{{Gallotannin Flavors Dihydroxybenzoic acids Gallotannins Vanilloids Phenol ethers