Vanillic acid explained

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.[1] [2]

Occurrence in nature

The highest amount of vanillic acid in plants known so far is found in the root of Angelica sinensis,[3] 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 .[4] It is one of the main natural phenols in argan oil. It is also found in wine and vinegar.[5]

Metabolism

Vanillic acid is one of the main catechins metabolites found in humans after consumption of green tea infusions.[6]

Synthesis

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.[7]

Notes and References

  1. Lesage-Meessen L, Delattre M, Haon M, Thibault JF, Ceccaldi BC, Brunerie P, Asther M . A two-step bioconversion process for vanillin production from ferulic acid combining Aspergillus niger and Pycnoporus cinnabarinus . J. Biotechnol. . 50 . 2–3 . 107–113 . October 1996 . 8987621 . 10.1016/0168-1656(96)01552-0.
  2. Civolani C, Barghini P, Roncetti AR, Ruzzi M, Schiesser A . Bioconversion of ferulic acid into vanillic acid by means of a vanillate-negative mutant of Pseudomonas fluorescens strain BF13 . Appl. Environ. Microbiol. . 66 . 6 . 2311–2317 . June 2000 . 10831404 . 110519 . 10.1128/AEM.66.6.2311-2317.2000 . 2000ApEnM..66.2311C .
  3. Book: Duke, JA . Handbook of phytochemical constituents of GRAS herbs and other economic plants . 1992 . CRC Press, 999 edition . 978-0-8493-3865-6 . 2012-01-07 . https://web.archive.org/web/20150923173938/http://www.ars-grin.gov/cgi-bin/duke/chemical.pl?VANILICACID . 2015-09-23 . dead .
  4. J Agric Food Chem . Jun 2008 . 56 . 12 . 4631–4636 . Chemical composition, antioxidant properties, and thermal stability of a phytochemical enriched oil from Açaí (Euterpe oleracea Mart.) . Pacheco-Palencia LA, Mertens-Talcott S, Talcott ST . 18522407. 10.1021/jf800161u.
  5. 10.1007/BF01192948. Analysis of polyphenolic compounds of different vinegar samples. Zeitschrift für Lebensmittel-Untersuchung und -Forschung. 199. 29–31. 1994. Gálvez. Miguel Carrero. Barroso. Carmelo García . Pérez-Bustamante. Juan Antonio. 91784893.
  6. 10.1002/biof.5520080119. 9699018. Catechin metabolites after intake of green tea infusions. BioFactors. 8. 1–2. 111–8. 1998. Pietta. P. G.. Simonetti. P.. Gardana. C.. Brusamolino. A.. Morazzoni. P.. Bombardelli. E.. 37684286.
  7. Lim M, Yoon CM, An G, Rhee H . Environmentally benign oxidation reaction of aldehydes to their corresponding carboxylic acids using Pd/C with NaBH4 and KOH . Tetrahedron Lett. . 2007 . 48 . 22 . 3835–3839. 10.1016/j.tetlet.2007.03.151 .

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