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Revision as of 05:02, 7 January 2012

Vanillic acid
Names
IUPAC name 4-Hydroxy-3-methoxybenzoic acid
Other names 4-Hydroxy-m-anisic acid, Vanillate
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.061 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)Key: WKOLLVMJNQIZCI-UHFFFAOYSA-N
  • 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
SMILES
  • COc1cc(ccc1O)C(=O)O
Properties
Chemical formula C8H8O4
Molar mass 168.14 g/mol
Appearance White to light yellow powder or crystals
Melting point 210–213 °C
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1 0 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

Vanillic acid UV visible spectrum

Occurrence in nature

The highest amount of vanillic acid in plants known so far is found in the root of Angelica sinensis,, a herb indigenous to China, which is used in traditional Chinese medicine.

Açaí oil, obtained from the fruit of the açaí palm (Euterpe oleracea), is rich in vanillic acid (1,616 +/- 94 mg/kg).

Metabolism

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

References

  1. "Vanillic acid (4-hydroxy-3-methoxybenzoic acid)". chemicalland21.com. Retrieved 2009-01-28. {{cite web}}: Cite has empty unknown parameter: |coauthors= (help)
  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): 107–13. doi:10.1016/0168-1656(96)01552-0. PMID 8987621. {{cite journal}}: 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): 2311–7. doi:10.1128/AEM.66.6.2311-2317.2000. PMC 110519. PMID 10831404. {{cite journal}}: 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 978-0849338656.
  5. "Chemical composition, antioxidant properties, and thermal stability of a phytochemical enriched oil from Acai (Euterpe oleracea Mart.)". J Agric Food Chem. 56 (12): 4631–6. 2008. doi:10.1021/jf800161u. PMID 18522407. {{cite journal}}: Unknown parameter |authors= ignored (help); Unknown parameter |month= ignored (help)
  6. 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
Types of gallotannins
Aglycones
Galloylglucoses
Monogalloylglucoses:
Digalloylglucoses:
Trigalloylglucoses:
Tetragalloylglucoses:
Pentagalloylglucoses:
other
Galloylquinic acids:
Monogalloylquinic acids:
Digalloylquinic acids:
Trigalloylquinic acids:
Galloylshikimic acids:
others

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