Vanillic acid

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Vanillic acid[1]
Vanillinsäure.svg
Names
IUPAC name
4-Hydroxy-3-methoxybenzoic acid
Other names
4-Hydroxy-m-anisic acid, Vanillate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.061
Properties
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. waterHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
0
1
0
Except where otherwise noted, 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

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 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

  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 (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. Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  3. ^ Civolani C, Barghini P, Roncetti AR, Ruzzi M, Schiesser A (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. Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  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 (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. Unknown parameter |month= ignored (help)CS1 maint: uses authors parameter (link)
  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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