| Revision as of 15:49, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 470027645 of page Vanillic_acid for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 23:40, 3 March 2024 edit Maxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,042 edits Added the cs1 style template to denote Vancouver ("vanc") citation style, because references contain "vauthors" attribute to specify the list of authors. Added bibcode. | Use this tool. Report bugs. | #UCB_Gadget |
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{{cs1 config|name-list-style=vanc}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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|verifiedrevid = 470628993 |
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|Reference =<ref name="urlVANILLIC ACID (3-METHOXY-4-HYDROXYBENZOIC ACID)">{{cite web | url = http://chemicalland21.com/lifescience/foco/VANILLIC%20ACID.htm | title = Vanillic acid (4-hydroxy-3-methoxybenzoic acid) | publisher = chemicalland21.com | access-date = 2009-01-28}}</ref> |
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| verifiedrevid = 419134593 |
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|ImageFileL1_Ref = {{chemboximage|correct|??}} |
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|Reference=<ref name="urlVANILLIC ACID (3-METHOXY-4-HYDROXYBENZOIC ACID)">{{cite web | url = http://chemicalland21.com/lifescience/foco/VANILLIC%20ACID.htm | title = Vanillic acid (4-hydroxy-3-methoxybenzoic acid) | author = | authorlink = | coauthors = | date = | work = | publisher = chemicalland21.com | pages = | language = | archiveurl = | archivedate = | quote = | accessdate = 2009-01-28}}</ref> |
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|ImageFileL1 =Kwas wanilinowy.svg |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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|ImageSizeL1 =130 |
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| ImageFile=Vanillinsäure.svg |
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|ImageAltL1 = Skeletal formula of vanillic acid |
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| ImageSize=150px |
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|ImageFileR1 = Vanillic acid 3D ball.png |
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| IUPACName=4-Hydroxy-3-methoxybenzoic acid |
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|ImageSizeR1 =145 |
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| OtherNames=4-Hydroxy-m-anisic acid, Vanillate |
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|ImageAltR1 = Ball-and-stick model of the vanillic acid molecule |
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|Section1= {{Chembox Identifiers |
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|PIN =4-Hydroxy-3-methoxybenzoic acid |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|OtherNames =4-Hydroxy-''m''-anisic acid, Vanillate |
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| ChemSpiderID = 8155 |
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|Section1={{Chembox Identifiers |
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| InChI = 1/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11) |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| InChIKey = WKOLLVMJNQIZCI-UHFFFAOYAH |
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|ChemSpiderID = 8155 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|InChI = 1/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11) |
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| ChEMBL = 120568 |
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|InChIKey = WKOLLVMJNQIZCI-UHFFFAOYAH |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| StdInChI = 1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11) |
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|ChEMBL = 120568 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = WKOLLVMJNQIZCI-UHFFFAOYSA-N |
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|StdInChI = 1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11) |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| CASNo=121-34-6 |
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|StdInChIKey = WKOLLVMJNQIZCI-UHFFFAOYSA-N |
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| PubChem=8468 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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|CASNo =121-34-6 |
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| ChEBI = 30816 |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES = COc1cc(ccc1O)C(=O)O |
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|UNII = GM8Q3JM2Y8 |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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|KEGG = C06672 |
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|PubChem =8468 |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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|ChEBI = 30816 |
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|SMILES = COc1cc(ccc1O)C(=O)O |
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}} |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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|C=8 | H=8 | O=4 |
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| Formula=C<sub>8</sub>H<sub>8</sub>O<sub>4</sub> |
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|Appearance =White to light yellow powder or crystals |
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| MolarMass= 168.14 g/mol |
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|MeltingPtC = 210 to 213 |
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| ExactMass = |
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| Appearance=White to light yellow powder or crystals |
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| Density= |
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| MeltingPt=210–213 °C |
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}} |
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|Section3= {{Chembox Hazards |
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| NFPA-H = 1 |
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| NFPA-F = 0 |
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| NFPA-R = 0 |
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|Section3={{Chembox Hazards |
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|NFPA-H = 1 |
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|NFPA-F = 0 |
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|NFPA-R = 0 |
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}} |
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|Section4={{Chembox Related |
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|OtherCompounds = ], ]}} |
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}} |
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'''Vanillic acid''' ('''4-hydroxy-3-methoxybenzoic acid''') is a ] derivative used as a flavoring agent. It is an ] form of ]. It is also an intermediate in the production of vanillin from ].<ref name="pmid8987621">{{cite journal | vauthors = Lesage-Meessen L, Delattre M, Haon M, Thibault JF, Ceccaldi BC, Brunerie P, Asther M | title = A two-step bioconversion process for vanillin production from ferulic acid combining Aspergillus niger and Pycnoporus cinnabarinus | journal = J. Biotechnol. | volume = 50 | issue = 2–3 | pages = 107–113 |date=October 1996 | pmid = 8987621 | doi = 10.1016/0168-1656(96)01552-0}}</ref><ref name="pmid10831404">{{cite journal | vauthors = Civolani C, Barghini P, Roncetti AR, Ruzzi M, Schiesser A | title = Bioconversion of ferulic acid into vanillic acid by means of a vanillate-negative mutant of Pseudomonas fluorescens strain BF13 | journal = Appl. Environ. Microbiol. | volume = 66 | issue = 6 | pages = 2311–2317 |date=June 2000 | pmid = 10831404 | pmc = 110519 | doi = 10.1128/AEM.66.6.2311-2317.2000 | bibcode = 2000ApEnM..66.2311C }}</ref> |
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== Occurrence in nature == |
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The highest amount of vanillic acid in plants known so far is found in the root of '']'',<ref>{{cite book | author = Duke, JA | title = Handbook of phytochemical constituents of GRAS herbs and other economic plants | year = 1992 | publisher = CRC Press, 999 edition | url = http://www.ars-grin.gov/cgi-bin/duke/chemical.pl?VANILICACID | isbn = 978-0-8493-3865-6 | access-date = 2012-01-07 | archive-url = https://web.archive.org/web/20150923173938/http://www.ars-grin.gov/cgi-bin/duke/chemical.pl?VANILICACID | archive-date = 2015-09-23 | url-status = dead }}</ref> an herb indigenous to China, which is used in ]. |
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=== Occurrences in food === |
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], obtained from the fruit of the açaí palm ('']''), is rich in vanillic acid ({{val|1,616|94|u=mg/kg}}).<ref>{{cite journal |journal = J Agric Food Chem |date=Jun 2008 | volume = 56 | issue = 12 | pages = 4631–4636 | title = Chemical composition, antioxidant properties, and thermal stability of a phytochemical enriched oil from Açaí (''Euterpe oleracea'' Mart.) | vauthors = Pacheco-Palencia LA, Mertens-Talcott S, Talcott ST |pmid = 18522407| doi = 10.1021/jf800161u}}</ref> It is one of the main natural phenols in ].{{Citation needed|date=December 2019|reason=removed citation to predatory publisher content}} It is also found in ] and ].<ref>{{Cite journal | doi = 10.1007/BF01192948| title = Analysis of polyphenolic compounds of different vinegar samples| journal = Zeitschrift für Lebensmittel-Untersuchung und -Forschung| volume = 199| pages = 29–31| year = 1994| last1 = Gálvez| first1 = Miguel Carrero| last2 = Barroso| first2 = Carmelo García | last3 = Pérez-Bustamante| first3 = Juan Antonio| s2cid = 91784893}}</ref> |
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== Metabolism == |
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Vanillic acid is one of the main ] ]s found in humans after consumption of ] infusions.<ref>{{Cite journal | doi = 10.1002/biof.5520080119| pmid = 9699018| title = Catechin metabolites after intake of green tea infusions| journal = BioFactors| volume = 8| issue = 1–2| pages = 111–8| year = 1998| last1 = Pietta| first1 = P. G.| last2 = Simonetti| first2 = P.| last3 = Gardana| first3 = C.| last4 = Brusamolino| first4 = A.| last5 = Morazzoni| first5 = P.| last6 = Bombardelli| first6 = E.| s2cid = 37684286}}</ref> |
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==Synthesis== |
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Vanillic acid can be obtained from the oxidation of ] by various oxidizing agents. With Pd/C, NaBH<sub>4</sub>, and KOH as the oxidizing agent, the conversion was reported to occur in ~89% yield.<ref>{{cite journal|vauthors=Lim M, Yoon CM, An G, Rhee H |title=Environmentally benign oxidation reaction of aldehydes to their corresponding carboxylic acids using Pd/C with NaBH4 and KOH |journal=Tetrahedron Lett. |date=2007 |volume=48 |issue=22 |pages=3835–3839|doi=10.1016/j.tetlet.2007.03.151 }}</ref> |
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== References == |
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{{Reflist}} |
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{{Gallotannin}} |
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