Vanillic acid

Vanillic acid ^[1]

Names
Preferred IUPAC name 4-Hydroxy-3-methoxybenzoic acid
Other names 4-Hydroxy-m-anisic acid, Vanillate
Identifiers
CAS Number	121-34-6  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:30816  Y
ChEMBL	ChEMBL120568  Y
ChemSpider	8155  Y
ECHA InfoCard	100.004.061
KEGG	C06672  Y
PubChem CID	8468
UNII	GM8Q3JM2Y8  Y
CompTox Dashboard (EPA)	DTXSID6059522
InChI InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11) Y Key: WKOLLVMJNQIZCI-UHFFFAOYSA-N Y 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	168.148 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). Y  verify  (what is  YN ?) 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

Vanillic acid can be obtained from the oxidation of vanillin by various oxidizing agents.

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. Bibcode:2000ApEnM..66.2311C. 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 MC, Barroso CG, Pérez-Bustamante JA (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 PG, 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.