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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:30816 ;
ChEMBL	ChEMBL120568 ;
ChemSpider	8155 ;
ECHA InfoCard	100.004.061
KEGG	C06672 ;
PubChem CID	8468;
UNII	GM8Q3JM2Y8 ;
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) 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	168.148 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). verify (what is ?) 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]

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[edit]

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[edit]

Vanillic acid is one of the main catechins metabolites found in humans after consumption of green tea infusions.^[7]

Synthesis[edit]

Vanillic acid can be obtained from the oxidation of vanillin by various oxidizing agents. With Pd/C, NaBH₄, and KOH as the oxidizing agent, the conversion was reported to occur in ~89% yield.^[8]

References[edit]

^ "Vanillic acid (4-hydroxy-3-methoxybenzoic acid)". chemicalland21.com. Retrieved 2009-01-28.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

[urlVANILLIC_ACID_(3-METHOXY-4-HYDROXYBENZOIC_ACID)-1] "Vanillic acid (4-hydroxy-3-methoxybenzoic acid)". chemicalland21.com. Retrieved 2009-01-28.

[pmid8987621-2] 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.

[pmid10831404-3] 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.

[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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]