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{{Short description|3,4,5-Trihydroxybenzoic acid}} |
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{{chembox |
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{{Chembox |
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| Watchedfields = changed |
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| verifiedrevid = 409743735 |
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| verifiedrevid = 443831396 |
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| Name = Gallic acid |
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| Name = Gallic acid |
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| ImageFileL1 = Gallic acid.svg |
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| ImageFileL1 = Gallic acid.svg |
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| ImageSizeL1 = 130px |
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| ImageSizeL1 = 120 |
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| ImageClassL1 = skin-invert |
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| ImageFileR1 = Gallic acid-3D.png |
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| ImageAltL1 = Skeletal formula |
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| ImageSizeR1 = 130px |
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| ImageName = Gallic acid |
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| ImageFileR1 = Gallic acid molecule spacefill from xtal.png |
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| ImageSizeR1 = 120 |
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| IUPACName = 3,4,5-trihydroxybenzoic acid |
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| ImageAltR1 = Space-filling model of gallic acid |
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| OtherNames = Gallic acid<br>Gallate<br>3,4,5-trihydroxybenzoate |
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| ImageName = Gallic acid |
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| Section1 = {{Chembox Identifiers |
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| PIN = 3,4,5-Trihydroxybenzoic acid |
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| ChEBI = 30778 |
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| OtherNames = Gallic acid |
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|Section1={{Chembox Identifiers |
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| IUPHAR_ligand = 5549 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 30778 |
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| SMILES = O=C(O)c1cc(O)c(O)c(O)c1 |
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| SMILES = O=C(O)c1cc(O)c(O)c(O)c1 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 632XD903SP |
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| UNII = 632XD903SP |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII1 = 48339473OT |
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| UNII1_Comment = (monohydrate) |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C01424 |
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| KEGG = C01424 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = LNTHITQWFMADLM-UHFFFAOYSA-N |
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| StdInChIKey = LNTHITQWFMADLM-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|??|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 149-91-7 |
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| CASNo = 149-91-7 |
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| CASNo2_Ref = {{cascite|correct|CAS}} |
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| CASOther = (Monohydrate) |
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| PubChem = 370 |
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| CASNo2 = 5995-86-8 |
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| CASNo2_Comment = (monohydrate) |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PubChem = 370 |
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| ChemSpiderID=361 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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}} |
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| ChemSpiderID = 361 |
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| Section2 = {{Chembox Properties |
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| EINECS = 205-749-9 |
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| Formula = C<sub>7</sub>H<sub>6</sub>O<sub>5</sub> |
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| RTECS = LW7525000 |
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| MolarMass = 170.12 g/mol |
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}} |
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| ExactMass = 170.021523 u |
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|Section2={{Chembox Properties |
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| Appearance = White, yellowish-white, or<br />pale fawn-colored crystals. |
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| Formula = C<sub>7</sub>H<sub>6</sub>O<sub>5</sub> |
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| Density = 1.7 g/cm<sup>3</sup> (anhydrous) |
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| MolarMass = 170.12 g/mol |
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| Solubility = 1.1 g/100 ml water @ 20°C (anhydrous)<br />1.5 g/100 ml water @ 20 °C (monohydrate) |
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| Appearance = White, yellowish-white, or<br />pale fawn-colored crystals. |
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| MeltingPtC = 250 |
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| Density = 1.694 g/cm<sup>3</sup> (anhydrous) |
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| BoilingPt = |
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| Solubility = 1.19 g/100 mL, 20°C (anhydrous)<br />1.5 g/100 mL, 20 °C (monohydrate) |
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| pKa = COOH: 4.5, OH: 10. |
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| SolubleOther = soluble in ], ], ], ] <br> negligible in ], ], ] |
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}} |
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| MeltingPtC = 260 |
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| Section3 = {{Chembox Structure |
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| CrystalStruct = |
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| BoilingPt = |
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| pKa = COOH: 4.5, OH: 10. |
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| Dipole = |
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| LogP = 0.70 |
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}} |
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| MagSus = -90.0·10<sup>−6</sup> cm<sup>3</sup>/mol |
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| Section7 = {{Chembox Hazards |
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}} |
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| ExternalMSDS = |
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|Section3={{Chembox Structure |
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| MainHazards = Irritant |
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| CrystalStruct = |
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}} |
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| Dipole = |
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| Section8 = {{Chembox Related |
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}} |
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| Function = ]s,<br />]s |
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|Section7={{Chembox Hazards |
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| OtherFunctn = |
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| ExternalSDS = |
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| OtherCpds = ], ], ] |
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| MainHazards = Irritant |
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}} |
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| NFPA-H = 1 |
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| NFPA-F = 0 |
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| LD50 = 5000 mg/kg (rabbit, oral) |
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}} |
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|Section8={{Chembox Related |
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| OtherFunction = ]s,<br />]s |
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| OtherCompounds = ], ], ] |
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}} |
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'''Gallic acid''' is a ], a type of phenolic acid, a type of organic acid, also known as 3,4,5-trihydroxy], found in ]s, ], ], ] leaves, ] ], and other ]s.<ref>LD Reynolds and NG Wilson, “Scribes and Scholars” 3rd Ed. Oxford: 1991. pp193–4.</ref> The chemical formula is ]<sub>6</sub>]<sub>2</sub>(])<sub>3</sub>COOH. Gallic acid is found both free and as part of ]s. ] and ]s of gallic acid are termed 'gallates'. Despite its name, it does not contain ]. |
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'''Gallic acid''' (also known as '''3,4,5-trihydroxybenzoic acid''') is a ] with the formula ]<sub>6</sub>]<sub>2</sub>(])<sub>3</sub>CO<sub>2</sub>H. It is classified as a ]. It is found in ]s, ], ], ] leaves, ], and other ]s.<ref name=Haslam_and_Cai>{{Cite journal | last1 = Haslam | first1 = E. | last2 = Cai | first2 = Y. | doi = 10.1039/NP9941100041 | title = Plant polyphenols (vegetable tannins): Gallic acid metabolism | journal = Natural Product Reports | volume = 11 | issue = 1 | pages = 41–66 | year = 1994 | pmid = 15206456}}</ref> It is a white solid, although samples are typically brown owing to partial oxidation. ]s and ]s of gallic acid are termed "gallates". |
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Its name is derived from ]s, which were historically used to prepare ]. Despite the name, gallic acid does not contain ]. |
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Gallic acid is commonly used in the pharmaceutical industry.<ref>{{cite web | author = S. M. Fiuza | title = Phenolic acid derivatives with potential anticancer properties––a structure–activity relationship study. Part 1: Methyl, propyl and octyl esters of caffeic and gallic acids | publisher = ] | doi = 10.1016/j.bmc.2004.04.026 }}</ref> It is used as a ] for determining the ] content of various analytes by the ]; results are reported in ''gallic acid equivalents''.<ref>{{cite web | author = Andrew Waterhouse | title = Folin-Ciocalteau Micro Method for Total Phenol in Wine | publisher = ] | url = http://waterhouse.ucdavis.edu/phenol/folinmicro.htm}}</ref> Gallic acid can also be used as a starting material in the synthesis of the psychedelic alkaloid ].<ref>{{cite journal |last=Tsao |first=Makepeasce |authorlink= |coauthors= |year=1951 |month=July |title=A New Synthesis Of Mescaline |journal=Journal of the American Chemical Society |volume=73 |issue=11 |pages=5495–5496|issn=0002-7863 |url= |accessdate=2009-05-02 |quote= |doi=10.1021/ja01155a562 }}</ref> |
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==Isolation and derivatives== |
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Gallic acid seems to have anti-fungal and anti-viral properties. Gallic acid acts as an antioxidant and helps to protect human cells against oxidative damage. Gallic acid was found to show cytotoxicity against cancer cells, without harming healthy cells. Gallic acid is used as a remote astringent in cases of internal haemorrhage. Gallic acid is also used to treat albuminuria and diabetes. Some ointments to treat psoriasis and external haemorrhoids contain gallic acid.<ref></ref> |
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] |
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] molecule structure resembles that of two gallic acid molecules assembled in head to tail position and linked together by a C–C bond (as in ]) and two cyclic ] (]s) forming two additional 6-piece cycles.]] |
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Gallic acid is easily freed from ]s by acidic or alkaline ]. When heated with concentrated ], gallic acid converts to ]. Hydrolyzable tannins break down on hydrolysis to give gallic acid and ] or ellagic acid and glucose, known as ]s and ]s, respectively.<ref>{{Citation |last=Andrew Pengelly |title=The Constituents of Medicinal Plants |pages=29–30 |year=2004 |edition=2nd |publisher=Allen & Unwin}}</ref> |
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=== Biosynthesis === |
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==Historical context and uses== |
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] |
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Gallic acid was one of the substances used by ] (1782–1854) among other early investigators of ]s to clear the top layer of text off and reveal hidden manuscripts underneath. Mai was the first to employ it, but did so "with a heavy hand", often damaging manuscripts for future study.{{Citation needed|date=March 2008}} |
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Gallic acid is formed from ] by the action of the enzyme ] to produce 3,5-didehydroshikimate. This latter compound ].<ref></ref><ref>{{Cite journal|pmc=1184696|year=1969|last1=Dewick|first1=PM|last2=Haslam|first2=E|title=Phenol Biosynthesis in Higher Plants. Gallic Acid|volume=113|issue=3|pages=537–542|journal=Biochemical Journal|pmid=5807212|doi=10.1042/bj1130537}}</ref> |
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===Reactions=== |
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It has been discovered by French chemist and pharmacist ] (1780–1855) in 1818 and studied by French chemist ] (1807–1867). |
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====Oxidation and oxidative coupling==== |
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Alkaline solutions of gallic acid are readily oxidized by air. The oxidation is catalyzed by the enzyme ], an enzyme found in '']''. |
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Oxidative coupling of gallic acid with arsenic acid, permanganate, persulfate, or iodine yields ], as does reaction of methyl gallate with ].<ref name="ull-hcaa" /> Gallic acid forms intermolecular esters (]) such as ] and cyclic ether-esters (]s).<ref name="ull-hcaa">{{citation | author=Edwin Ritzer | author2=Rudolf Sundermann | contribution=Hydroxycarboxylic Acids, Aromatic | title=Ullmann's Encyclopedia of Industrial Chemistry | edition=7th | publisher=Wiley | year=2007 | page=6| title-link=Ullmann's Encyclopedia of Industrial Chemistry }}</ref> |
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Early photographers also used it, ] (1801–1870) for instance and ] (1800–1877) for developing latent images in ]s. It has also been used as a coating agent in ]. |
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====Hydrogenation==== |
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] of gallic acid gives the cyclohexane derivative hexahydrogallic acid.<ref>{{cite journal |doi=10.15227/orgsyn.042.0062|title=Hexahydrogallic Acid and Hexahydrogallic Acid Triacetate|journal=Organic Syntheses|year=1962|volume=42|page=62|author=Albert W. Burgstahler and Zoe J. Bithos}}</ref> |
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====Decarboxylation==== |
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Heating gallic acid gives ] (1,2,3-trihydroxybenzene). This conversion is catalyzed by ]. |
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====Esterification==== |
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Many esters of gallic acid are known, both synthetic and natural. ] catalyzes the ] (attachment of glucose) of gallic acid. |
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== Historical context and uses == |
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It was also used by ] to communicate with spies during the United States war for independence (American Revolution) according to the miniseries "''America the Story of Us''." |
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Gallic acid is an important component of ], the standard European writing and drawing ink from the 12th to 19th centuries, with a history extending to the Roman empire and the ]. ] (23–79 AD) describes the use of gallic acid as a means of detecting an adulteration of ]<ref>Pliny the Elder with John Bostock and H.T. Riley, trans., ''The Natural History of Pliny'' (London, England: Henry G. Bohn, 1857), vol. 6, In Book 34, Chapter 26 of his ''Natural History'', Pliny states that verdigris (a form of copper acetate (Cu(CH<sub>3</sub>COO)<sub>2</sub>·2Cu(OH)<sub>2</sub>), which was used to process leather, was sometimes adulterated with copperas (a form of iron(II) sulfate (FeSO<sub>4</sub>·7H<sub>2</sub>O)). He presented a simple test for determining the purity of verdigris. From p. 196: "The adulteration , however, which is most difficult to detect, is made with copperas; ... The fraud may also be detected by using a leaf of papyrus, which has been steeped in an infusion of nut-galls; for it becomes black immediately upon the genuine verdigris being applied."</ref> and writes that it was used to produce dyes. Galls (also known as oak apples) from oak trees were crushed and mixed with water, producing ]. It could then be mixed with ] (])—obtained by allowing sulfate-saturated water from a spring or mine drainage to evaporate{{citation needed|date=October 2021}}—and ] from acacia trees; this combination of ingredients produced the ink.<ref>{{cite web|last=Fruen|first=Lois|title=Iron Gall Ink|url=http://www.realscience.breckschool.org/upper/fruen/files/Enrichmentarticles/files/IronGallInk/IronGallInk.html|url-status=dead|archive-url=https://web.archive.org/web/20111002191808/http://www.realscience.breckschool.org/upper/fruen/files/Enrichmentarticles/files/IronGallInk/IronGallInk.html|archive-date=2011-10-02}}</ref> |
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Gallic acid was one of the substances used by ] (1782–1854), among other early investigators of ]s, to clear the top layer of text off and reveal hidden manuscripts underneath. Mai was the first to employ it, but did so "with a heavy hand", often rendering manuscripts too damaged for subsequent study by other researchers.<ref>L.D. Reynolds and N.G. Wilson, "Scribes and Scholars" 3rd Ed. Oxford: 1991, pp 193–4.</ref> |
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Gallic acid is a component of some ]tures. |
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Gallic acid was first studied by the Swedish chemist ] in 1786.<ref>Carl Wilhelm Scheele (1786) (On the essential salt of galls or gall-salt), ''Kongliga Vetenskaps Academiens nya Handlingar'' (Proceedings of the Royal Academy of Science), '''7''': 30–34.</ref> In 1818, French chemist and pharmacist ] (1780–1855) devised a simpler method of purifying gallic acid from galls;<ref>{{cite journal | author = Braconnot Henri | year = 1818 | url = https://books.google.com/books?id=OwXcSjJbARAC&pg=PA181 |title=Observations sur la préparation et la purification de l'acide gallique, et sur l'existence d'un acide nouveau dans la noix de galle |trans-title=Observations on the preparation and purification of gallic acid, and on the existence of a new acid in galls | journal = Annales de Chimie et de Physique | volume = 9 | pages = 181–184 }}</ref> gallic acid was also studied by the French chemist ] (1807–1867),<ref>J. Pelouze (1833) ''Annales de chimie et de physique'', '''54''': 337–365 .</ref> among others. |
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== List of plants or foods that contain the chemical == |
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* ] |
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* ] (''Arctostaphylos sp'') |
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* ''] sp'' |
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* ] |
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* '']''<ref name=Kilburn>Antimicrobial gallic acid from Caesalpinia mimosoides Lamk. Anchana Chanwitheesuk, Aphiwat Teerawutgulrag, Jeremy D. Kilburn and Nuansri Rakariyatham, Food Chemistry, Volume 100, Issue 3, 2007, pp. 1044-1048, {{doi|10.1016/j.foodchem.2005.11.008}}</ref> |
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* ] |
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* '']'' (sundew) |
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* '']'' (Common walnut) |
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* ] in peels and leaves |
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* '']'' (Indian gooseberry) in fruits |
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* ] |
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* '']'' (clove)<ref name=tdmq>{{cite journal |
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| last = Pathak |
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| first = S. B. ''et al.'' |
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| authorlink = |
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| coauthors = |
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| title = TLC Densitometric Method for the Quantification of Eugenol and Gallic Acid in Clove |
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| journal = Chromatographia |
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| volume = 60 |
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| issue = 3 - 4 |
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| pages = 241–244 |
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| publisher = |
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| location = |
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| year = 2004 |
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| url = |
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| issn = |
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| doi = 10.1365/s10337-004-0373-y |
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| id = |
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| accessdate = 28 June 2009 |
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| last2 = Niranjan |
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| first2 = K. |
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| last3 = Padh |
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| first3 = H. |
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| last4 = Rajani |
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| first4 = M.}}</ref> |
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* '']'' (Golden root) |
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* ] (Ayurvedic herbal rasayana formula) |
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* ] (''Hamamelis virginiana'') |
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* ] |
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When mixed with ], gallic acid had uses in early types of photography, like the ] to make the silver more sensitive to light; it was also used in developing photographs.<ref>{{Cite book |last1=Taylor |first1=Roger |url=https://books.google.com/books?id=DnfBcmW-OkYC&pg=PA65 |title=Impressed by Light: British Photographs from Paper Negatives, 1840-1860 |last2=Schaaf |first2=Larry John |date=2007 |publisher=Metropolitan Museum of Art |isbn=978-1-58839-225-1 |language=en}}</ref> |
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==Spectral data== |
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== Occurrence == |
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Gallic acid is found in a number of ]s, such as the ] '']'',<ref>{{cite journal |last1=Zucca |first1=Paolo |last2=Rosa |first2=Antonella |last3=Tuberoso |first3=Carlo |last4=Piras |first4=Alessandra |last5=Rinaldi |first5=Andrea |last6=Sanjust |first6=Enrico |last7=Dessì |first7=Maria |last8=Rescigno |first8=Antonio |title=Evaluation of Antioxidant Potential of "Maltese Mushroom" (Cynomorium coccineum) by Means of Multiple Chemical and Biological Assays |journal=Nutrients |date=11 January 2013 |volume=5 |issue=1 |pages=149–161 |doi=10.3390/nu5010149 |pmid=23344249 |pmc=3571642|doi-access=free }}</ref> the ] '']'', and the blue-green ] '']''.<ref name="Nakai">{{Cite journal |doi=10.1016/S0043-1354(00)00039-7 |title=Myriophyllum spicatum-released allelopathic polyphenols inhibiting growth of blue-green algae Microcystis aeruginosa |year=2000 |last1=Nakai |first1=S |journal=Water Research |volume=34 |issue=11 |pages=3026–3032|bibcode=2000WatRe..34.3026N }}</ref> Gallic acid is also found in various oak species,<ref>{{Cite journal|last2=Savolainen|first2=Heikki|last3=Lindroos|first3=Lasse|last4=Kangas|first4=Juhani|last5=Vartiainen|first5=Terttu|year=2000|title=Analysis of oak tannins by liquid chromatography-electrospray ionisation mass spectrometry|journal=Journal of Chromatography A|volume=891|issue=1|pages=75–83|doi=10.1016/S0021-9673(00)00624-5|pmid=10999626|last1=Mämmelä|first1=Pirjo}}</ref> ''],''<ref name="Kilburn">{{Cite journal|last2=Teerawutgulrag|first2=Aphiwat|last3=Kilburn|first3=Jeremy D.|last4=Rakariyatham|first4=Nuansri|year=2007|title=Antimicrobial gallic acid from Caesalpinia mimosoides Lamk|journal=Food Chemistry|volume=100|issue=3|pages=1044–1048|doi=10.1016/j.foodchem.2005.11.008|last1=Chanwitheesuk|first1=Anchana}}</ref> and in the stem bark of ''],''<ref>{{cite journal|last2=Onawunmi|first2=Grace O.|last3=Olugbade|first3=Tiwalade A.|year=2007|title=Antibacterial phenolics from Boswellia dalzielii|url=http://www.ajol.info/index.php/njnpm/article/view/11864|journal=Nigerian Journal of Natural Products and Medicine|volume=10|issue=1|pages=108–10|last1=Alemika|first1=Taiwo E.}}</ref> among others. Many foodstuffs contain various amounts of gallic acid, especially fruits (including strawberries, grapes, bananas),<ref name="pmid26251571">{{cite journal|year=2015|title=Gallic acid attenuates dextran sulfate sodium-induced experimental colitis in BALB/c mice|journal=Drug Design, Development and Therapy|volume=9|pages=3923–34|doi=10.2147/DDDT.S86345|pmc=4524530|pmid=26251571|vauthors=Pandurangan AK, Mohebali N, Norhaizan ME, Looi CY |doi-access=free }}</ref><ref>{{Cite journal|last2=Goto-Yamamoto|first2=N|last3=Hashizume|first3=K|year=2007|title=Influence of maceration temperature in red wine vinification on extraction of phenolics from berry skins and seeds of grape (Vitis vinifera)|journal=Bioscience, Biotechnology, and Biochemistry|volume=71|issue=4|pages=958–65|doi=10.1271/bbb.60628|pmid=17420579|last1=Koyama|first1=K|doi-access=free}}</ref> as well as ]s,<ref name="pmid26251571" /><ref>{{cite journal|year=2000|title=Gallic acid metabolites are markers of black tea intake in humans|journal=Journal of Agricultural and Food Chemistry|volume=48|issue=6|pages=2276–80|doi=10.1021/jf000089s|pmid=10888536|vauthors=Hodgson JM, Morton LW, Puddey IB, Beilin LJ, Croft KD}}</ref> cloves,<ref name="tdmq">{{cite journal|last1=Pathak|first1=S. B.|last2=Niranjan|first2=K.|last3=Padh|first3=H.|last4=Rajani|first4=M.|year=2004|title=TLC Densitometric Method for the Quantification of Eugenol and Gallic Acid in Clove|journal=Chromatographia|volume=60|issue=3–4|pages=241–244|doi=10.1365/s10337-004-0373-y|s2cid=95396304|display-authors=etal}}</ref> and ]s.<ref>{{Cite journal|last2=Barroso|first2=Carmelo García|last3=Pérez-Bustamante|first3=Juan Antonio|year=1994|title=Analysis of polyphenolic compounds of different vinegar samples|journal=Zeitschrift für Lebensmittel-Untersuchung und -Forschung|volume=199|pages=29–31|doi=10.1007/BF01192948|last1=Gálvez|first1=Miguel Carrero|s2cid=91784893}}</ref>{{Clarify|date=November 2016|reason=Type(s) of vinegar unstated, as well as quantity of gallic acid present.}} ] fruit is a rich source of gallic acid (24–165 mg per 100 g).<ref name="Goulas">{{cite journal | last1=Goulas | first1=Vlasios | last2=Stylos | first2=Evgenios | last3=Chatziathanasiadou | first3=Maria | last4=Mavromoustakos | first4=Thomas | last5=Tzakos | first5=Andreas | title=Functional Components of Carob Fruit: Linking the Chemical and Biological Space | journal=International Journal of Molecular Sciences | volume=17 | issue=11 | date=10 November 2016 | issn=1422-0067 | doi=10.3390/ijms17111875 | page=1875|pmid=27834921|pmc=5133875| doi-access=free }}</ref> |
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== Esters == |
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! {{chembox header}} | ] |
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Also known as galloylated esters: |
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* ] |
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* ], a food additive with E number E313 |
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| <!-- min (C<sub>18</sub> RP,)<ref></ref> --> |
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* ], or propyl 3,4,5-trihydroxybenzoate, an ester formed by the condensation of gallic acid and ] |
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* ], the ester of octanol and gallic acid |
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* ], or lauryl gallate, the ester of dodecanol and gallic acid |
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* ], a flavan-3-ol, a type of flavonoid, present in green tea |
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* ] (EGCG), also known as epigallocatechin 3-gallate, the ester of epigallocatechin and gallic acid, and a type of catechin |
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* ] (GCG), the ester of gallocatechin and gallic acid and a type of flavan-3ol |
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* ], a theaflavin derivative |
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Gallate esters are ]s useful in food preservation, with propyl gallate being the most commonly used. Their use in human health is scantly supported by evidence. |
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== Spectral data == |
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{| style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;" border="1" cellspacing="0" cellpadding="3" |
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| ] (log ε) |
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| ] (log ε) |
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| Major absorption bands |
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| Major absorption bands |
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| ν : 3491, 3377, 1703, 1617, 1539, 1453, 1254 ]<sup>−1</sup> (KBr) |
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| ν : 3491, 3377, 1703, 1617, 1539, 1453, 1254 cm<sup>−1</sup> (KBr) |
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<br>(acetone-d6): <!-- Link to image of spectrum --> |
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<br>(acetone-d6): <!-- Link to image of spectrum --> |
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<br>d : doublet, dd : doublet of doublets, |
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<br>d : doublet, dd : doublet of doublets, |
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| Other NMR data <!-- Insert special data e.g. <sup>19</sup>F chem. shifts, omit if not used --> |
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| Other NMR data <!-- Insert special data e.g. <sup>19</sup>F chem. shifts, omit if not used --> |
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| Masses of <br>main fragments |
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| Masses of <br>main fragments |
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| ESI-MS - m/z : 169.0137 |
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| ESI-MS - m/z : 169.0137 ms/ms (iontrap)@35 CE m/z product 125(100), 81(<1) |
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Reference<ref name=Kilburn/> |
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<ref name="Kilburn" /> |
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==Esters== |
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== See also == |
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* ] |
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* ], a food additive with E number E313 |
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* ] |
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* ], or propyl 3,4,5-trihydroxybenzoate, an ester formed by the condensation of gallic acid and propanol |
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* ] |
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* ], the ester of octanol and gallic acid |
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* ] |
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* ], or lauryl gallate, the ester of dodecanol and gallic acid |
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* ] |
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* ], a flavan-3-ol, a type of flavonoid, present in green tea |
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* ] |
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* ] (EGCG), also known as epigallocatechin 3-gallate, the ester of epigallocatechin and gallic acid, and a type of catechin |
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* ] |
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* ] (GCG), the ester of gallocatechin and gallic acid and a type of flavan-3ol |
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* ] |
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* ], a theaflavin derivative |
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==Metabolism== |
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== References == |
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] (EC 2.4.1.136) is an enzyme that uses UDP-glucose and gallate, whereas its two products are UDP and 1-galloyl-beta-D-glucose. |
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] (EC 4.1.1.59)is another enzyme. |
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==See also== |
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==References== |
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{{Reflist}} |
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{{Reflist}} |
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==External links== |
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{{Antioxidants}} |
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{{Gallotannin}} |
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{{Gallotannin}} |
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{{Phenolic acid}} |
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{{Phenolic acid}} |
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{{Authority control}} |
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{{DEFAULTSORT:Gallic Acid}} |
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{{DEFAULTSORT:Gallic Acid}} |
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