Vanillic acid

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Vanillic acid[1]
Names
IUPAC name
4-Hydroxy-3-methoxybenzoic acid
Other names
4-Hydroxy-m-anisic acid, Vanillate
Identifiers
121-34-6 YesY
ChEBI CHEBI:30816 YesY
ChEMBL ChEMBL120568 YesY
ChemSpider 8155 YesY
Jmol 3D model Interactive image
PubChem 8468
  • InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11) YesY
    Key: WKOLLVMJNQIZCI-UHFFFAOYSA-N YesY
  • 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
  • COc1cc(ccc1O)C(=O)O
Properties
C8H8O4
Molar mass 168.14 g/mol
Appearance White to light yellow powder or crystals
Melting point 210 to 213 °C (410 to 415 °F; 483 to 486 K)
Vapor pressure {{{value}}}
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).
YesY verify (what is YesYN ?)
Infobox references

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]

Occurrence in nature

File:Vanillic acid UV visible spectrum.png
Vanillic acid UV visible spectrum

The highest amount of vanillic acid in plants known so far is found in the root of Angelica sinensis,[4] a 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 (1,616 ± 94 mg/kg).[5]

It is one of the main natural phenols in argan oil.[6]

It is also found in wine and vinegar.[7]

Metabolism

Vanillic acid is one of the main catechins metabolites found in humans after consumption of green tea infusions.[8]

References

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  6. Phenols and Polyphenols from Argania spinosa. Z. Charrouf and D. Guillaume, American Journal of Food Technology, 2007, 2, pp. 679–683, doi:10.3923/ajft.2007.679.683
  7. Analysis of polyphenolic compounds of different vinegar samples. Miguel Carrero Gálvez, Carmelo García Barroso and Juan Antonio Pérez-Bustamante, Zeitschrift für Lebensmitteluntersuhung und -Forschung A, Volume 199, Number 1, pp. 29–31, doi:10.1007/BF01192948
  8. Catechin metabolites after intake of green tea infusions. P. G. Pietta, P. Simonetti, C. Gardana, A. Brusamolino, P. Morazzoni and E. Bombardelli, BioFactors, 1998, Volume 8, Issue 1–2, pp. 111–118,doi:10.1002/biof.5520080119


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