Misplaced Pages

Vanillic acid: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively← Previous editContent deleted Content addedVisualWikitext
Revision as of 05:02, 7 January 2012 editZéroBot (talk | contribs)704,777 editsm r2.7.1) (Robot: Adding ja:バニリン酸← Previous edit Latest revision as of 23:40, 3 March 2024 edit undoMaxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,043 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 
(57 intermediate revisions by 35 users not shown)
Line 1: Line 1:
{{cs1 config|name-list-style=vanc}}
{{chembox {{chembox
| Verifiedfields = changed |Watchedfields = changed
|verifiedrevid = 470628993
| Watchedfields = changed
|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>
| verifiedrevid = 419134593
|ImageFileL1_Ref = {{chemboximage|correct|??}}
|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>
|ImageFileL1 =Kwas wanilinowy.svg
| ImageFile_Ref = {{chemboximage|correct|??}}
|ImageSizeL1 =130
| ImageFile=Vanillinsäure.svg
|ImageAltL1 = Skeletal formula of vanillic acid
| ImageSize=150px
|ImageFileR1 = Vanillic acid 3D ball.png
| IUPACName=4-Hydroxy-3-methoxybenzoic acid
|ImageSizeR1 =145
| OtherNames=4-Hydroxy-m-anisic acid, Vanillate
|ImageAltR1 = Ball-and-stick model of the vanillic acid molecule
|Section1= {{Chembox Identifiers
|PIN =4-Hydroxy-3-methoxybenzoic acid
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|OtherNames =4-Hydroxy-''m''-anisic acid, Vanillate
| ChemSpiderID = 8155
|Section1={{Chembox Identifiers
| InChI = 1/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| InChIKey = WKOLLVMJNQIZCI-UHFFFAOYAH
|ChemSpiderID = 8155
| ChEMBL_Ref = {{ebicite|correct|EBI}}
|InChI = 1/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)
| ChEMBL = 120568
|InChIKey = WKOLLVMJNQIZCI-UHFFFAOYAH
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|ChEMBL_Ref = {{ebicite|correct|EBI}}
| StdInChI = 1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)
|ChEMBL = 120568
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WKOLLVMJNQIZCI-UHFFFAOYSA-N
|StdInChI = 1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)
| CASNo_Ref = {{cascite|correct|CAS}}
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| CASNo=121-34-6
|StdInChIKey = WKOLLVMJNQIZCI-UHFFFAOYSA-N
| PubChem=8468
| ChEBI_Ref = {{ebicite|changed|EBI}} |CASNo_Ref = {{cascite|correct|CAS}}
|CASNo =121-34-6
| ChEBI = 30816
|UNII_Ref = {{fdacite|correct|FDA}}
| SMILES = COc1cc(ccc1O)C(=O)O
|UNII = GM8Q3JM2Y8
|KEGG_Ref = {{keggcite|correct|kegg}}
|KEGG = C06672
|PubChem =8468
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI = 30816
|SMILES = COc1cc(ccc1O)C(=O)O
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
|C=8 | H=8 | O=4
| Formula=C<sub>8</sub>H<sub>8</sub>O<sub>4</sub>
|Appearance =White to light yellow powder or crystals
| MolarMass= 168.14 g/mol
|MeltingPtC = 210 to 213
| ExactMass =
}}
| Appearance=White to light yellow powder or crystals
|Section3={{Chembox Hazards
| Density=
|NFPA-H = 1
| MeltingPt=210–213&nbsp;°C
|NFPA-F = 0
| BoilingPt=
|NFPA-R = 0
| Solubility=
}} }}
|Section3= {{Chembox Hazards |Section4={{Chembox Related
|OtherCompounds = ], ]}}
| MainHazards=
| FlashPt=
| Autoignition=
| NFPA-H = 1
| NFPA-F = 0
| NFPA-R = 0
| NFPA-O =
}}
}} }}
'''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 | author = 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 = 107–13 | year = 1996 | month = October | pmid = 8987621 | doi = 10.1016/0168-1656(96)01552-0| url = }}</ref><ref name="pmid10831404">{{cite journal | author = 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 = 2311–7 | year = 2000 | month = June | pmid = 10831404 | pmc = 110519 | doi = 10.1128/AEM.66.6.2311-2317.2000 | url = }}</ref>
]


'''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>
==Occurrence in nature==
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 = 978-0849338656}}</ref>, a herb indigenous to China, which is used in ].


== Occurrence in nature ==
], obtained from the fruit of the açaí palm (''Euterpe oleracea''), is rich in vanillic acid (1,616 +/- 94 mg/kg).<ref>{{cite journal |journal = J Agric Food Chem | year = 2008 | month = Jun | volume = 56 | issue = 12 | pages = 4631–6 | title = Chemical composition, antioxidant properties, and thermal stability of a phytochemical enriched oil from Acai (Euterpe oleracea Mart.) | authors = Pacheco-Palencia LA, Mertens-Talcott S, Talcott ST |PMID = 18522407| doi = 10.1021/jf800161u}}</ref>
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 ].


=== Occurrences in food ===
==Metabolism==
], 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>
Vanillic acid is one of the main ] ]s found in humans after consumption of ] infusions.<ref>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}}</ref>


==References== == Metabolism ==
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>

==Synthesis==
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>

== References ==
{{Reflist}} {{Reflist}}


Line 64: Line 69:


] ]
]
] ]
] ]
] ]
] ]

{{Natural-phenol-stub}}

]
]
]
]

Latest revision as of 23:40, 3 March 2024

Vanillic acid
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
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.061 Edit this at Wikidata
KEGG
PubChem CID
UNII
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 168.148 g·mol
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)
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
Related compounds
Related compounds Vanillin, vanillyl alcohol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY 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.

Occurrence in nature

The highest amount of vanillic acid in plants known so far is found in the root of Angelica sinensis, 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). It is one of the main natural phenols in argan oil. It is also found in wine and vinegar.

Metabolism

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

Synthesis

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.

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.
  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.
Types of gallotannins
Aglycones
Galloylglucoses
Monogalloylglucoses:
Digalloylglucoses:
Trigalloylglucoses:
Tetragalloylglucoses:
Pentagalloylglucoses:
other
Galloylquinic acids:
Monogalloylquinic acids:
Digalloylquinic acids:
Trigalloylquinic acids:
Galloylshikimic acids:
others
Categories: