Vanillic acid

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]

Vanillic acid^[1]

Names
Preferred IUPAC name 4-Hydroxy-3-methoxybenzoic acid
Other names 4-Hydroxy-m-anisic acid, Vanillate
Identifiers
CAS Number	121-34-6 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:30816 Y
ChEMBL	ChEMBL120568 Y
ChemSpider	8155 Y
ECHA InfoCard	100.004.061
KEGG	C06672 Y
PubChem CID	8468
UNII	GM8Q3JM2Y8 Y
CompTox Dashboard (EPA)	DTXSID6059522
InChI InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11) Y Key: WKOLLVMJNQIZCI-UHFFFAOYSA-N Y InChI=1/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11) Key: WKOLLVMJNQIZCI-UHFFFAOYAH
SMILES COc1cc(ccc1O)C(=O)O
Properties
Chemical formula	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)	1 0 0
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). Y verify (what is YN ?) Infobox references

Occurrence in nature

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.

Occurrences in food

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]

Metabolism

Vanillic acid is one of the main catechins metabolites found in humans after consumption of green tea infusions.^[7]

Synthesis

Vanillic acid can be obtained from the oxidation of vanillin by various oxidizing agents.