Vanillic acid

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Vanillic acid[1]
Kwas wanilinowy.svg
Identifiers
CAS number 121-34-6 YesY
PubChem 8468
ChemSpider 8155 YesY
ChEBI CHEBI:30816 YesY
ChEMBL CHEMBL120568 YesY
Jmol-3D images Image 1
Properties
Molecular formula C8H8O4
Molar mass 168.14 g/mol
Appearance White to light yellow powder or crystals
Melting point 210–213 °C
Hazards
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Related compounds
Related compounds Vanillin, vanillyl alcohol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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[edit]

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[edit]

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[edit]

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

References[edit]

  1. ^ "Vanillic acid (4-hydroxy-3-methoxybenzoic acid)". chemicalland21.com. Retrieved 2009-01-28. 
  2. ^ Lesage-Meessen L, Delattre M, Haon M, Thibault JF, Ceccaldi BC, Brunerie P, Asther M (October 1996). "A two-step bioconversion process for vanillin production from ferulic acid combining Aspergillus niger and Pycnoporus cinnabarinus". J. Biotechnol. 50 (2–3): 107–113. doi:10.1016/0168-1656(96)01552-0. PMID 8987621. 
  3. ^ Civolani C, Barghini P, Roncetti AR, Ruzzi M, Schiesser A (June 2000). "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. doi:10.1128/AEM.66.6.2311-2317.2000. PMC 110519. PMID 10831404. 
  4. ^ Duke, JA (1992). Handbook of phytochemical constituents of GRAS herbs and other economic plants. CRC Press, 999 edition. ISBN 978-0-8493-3865-6. 
  5. ^ Pacheco-Palencia LA, Mertens-Talcott S, Talcott ST (Jun 2008). "Chemical composition, antioxidant properties, and thermal stability of a phytochemical enriched oil from Acai (Euterpe oleracea Mart.)". J Agric Food Chem 56 (12): 4631–4636. doi:10.1021/jf800161u. PMID 18522407. 
  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