Vanillic acid (4-hydroxy-3-methoxybenzoic acid) is a dihydroxybenzoic acid derivative used as a flavoring agent. It is an oxidized form of vanillin. It is also an intermediate in the production of vanillin from ferulic acid.[2][3]
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Names | |||
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Preferred IUPAC name
4-Hydroxy-3-methoxybenzoic acid | |||
Other names
4-Hydroxy-m-anisic acid, Vanillate | |||
Identifiers | |||
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3D model (JSmol) |
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ChEBI | |||
ChEMBL | |||
ChemSpider |
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ECHA InfoCard | 100.004.061 | ||
KEGG |
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PubChem CID |
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UNII | |||
CompTox Dashboard (EPA) |
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Properties | |||
C8H8O4 | |||
Molar mass | 168.148 g·mol−1 | ||
Appearance | White to light yellow powder or crystals | ||
Melting point | 210 to 213 °C (410 to 415 °F; 483 to 486 K) | ||
Hazards | |||
NFPA 704 (fire diamond) | |||
Related compounds | |||
Related compounds |
Vanillin, vanillyl alcohol | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
The highest amount of vanillic acid in plants known so far is found in the root of Angelica sinensis,[4] an herb indigenous to China, which is used in traditional Chinese medicine.
Açaí oil, obtained from the fruit of the açaí palm (Euterpe oleracea), is rich in vanillic acid (1616±94 mg/kg).[5] It is one of the main natural phenols in argan oil.[citation needed] It is also found in wine and vinegar.[6]
Vanillic acid is one of the main catechins metabolites found in humans after consumption of green tea infusions.[7]
Vanillic acid can be obtained from the oxidation of vanillin by various oxidizing agents. With Pd/C, NaBH4, and KOH as the oxidizing agent, the conversion was reported to occur in ~89% yield.[8]