page_title: Gallic acid
section_title: Biosynthesis
hierarchical_section_title: Gallic acid / Metabolism / Biosynthesis
caption_attribution_description: English: chemical structure of 3,5-didehydroshikimate
context_page_description: Gallic acid is a trihydroxybenzoic acid, a type of phenolic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. The chemical formula of gallic acid is C₆H₂(OH)₃COOH. It is found both free and as part of hydrolyzable tannins. The gallic acid groups are usually bonded to form dimers such as ellagic acid. Hydrolyzable tannins break down on hydrolysis to give gallic acid and glucose or ellagic acid and glucose, known as gallotannins and ellagitannins, respectively.
  Gallic acid forms intermolecular esters such as digallic and trigallic acids, and cyclic ether-esters.
  Gallic acid is commonly used in the pharmaceutical industry as a standard for determining the phenol content of various analytes by the Folin-Ciocalteau assay; results are reported in gallic acid equivalents. Gallic acid can also be used as a starting material in the synthesis of the psychedelic alkaloid mescaline.
  The name is derived from oak galls, which were historically used to prepare tannic acid. Despite the name, gallic acid does not contain gallium. Salts and esters of gallic acid are termed "gallates".
context_section_description: Gallic acid is formed from 3-dehydroshikimate by the action of the enzyme shikimate dehydrogenase to produce 3,5-didehydroshikimate. This latter compound tautomerizes to form the redox equivalent gallic acid, where the equilibrium lies essentially entirely toward gallic acid because of the coincidentally occurring aromatization.
caption: Chemical structure of 3,5-didehydroshikimate
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