Vanillic acid

From Wikipedia, the free encyclopedia
Vanillic acid[1]
Skeletal formula of vanillic acid
Ball-and-stick model of the vanillic acid molecule
Names
Preferred 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 Edit this at Wikidata
UNII
Properties
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).
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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[]

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[]

Oxidation of vanillin to the carboxylic acid occurred in ~88% yield.[8]

Uses[]

Vanillic acid is used in the synthesis of:

  1. the analeptic drug etamivan.[9]
  3. Vanillic acid is acetylated and converted to its acid chloride; S.B. amidation with bromhexine gives .[10]
  5. (need synthesis still).

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 (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. Archived from the original on 2015-09-23. Retrieved 2012-01-07.
  5. ^ Pacheco-Palencia LA, Mertens-Talcott S, Talcott ST (Jun 2008). "Chemical composition, antioxidant properties, and thermal stability of a phytochemical enriched oil from Açaí (Euterpe oleracea Mart.)". J Agric Food Chem. 56 (12): 4631–4636. doi:10.1021/jf800161u. PMID 18522407.
  6. ^ Gálvez, Miguel Carrero; Barroso, Carmelo García; Pérez-Bustamante, Juan Antonio (1994). "Analysis of polyphenolic compounds of different vinegar samples". Zeitschrift für Lebensmittel-Untersuchung und -Forschung. 199: 29–31. doi:10.1007/BF01192948. S2CID 91784893.
  7. ^ Pietta, P. G.; Simonetti, P.; Gardana, C.; Brusamolino, A.; Morazzoni, P.; Bombardelli, E. (1998). "Catechin metabolites after intake of green tea infusions". BioFactors. 8 (1–2): 111–8. doi:10.1002/biof.5520080119. PMID 9699018. S2CID 37684286.
  8. ^ Lim M, Yoon CM, An G, Rhee H (2007). "Environmentally benign oxidation reaction of aldehydes to their corresponding carboxylic acids using Pd/C with NaBH4 and KOH". Tetrahedron Lett. 48 (22): 3835–3839. doi:10.1016/j.tetlet.2007.03.151.
  9. ^ Kvasnicka Erich, Kratzl Karl U.S. Patent 2,641,612 (1952 to Chemie Linz AG).
  10. ^ GB1432904A
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