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tiếng việt 中文 edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia 3 4 5 trihydroxybenzoic acid gallic acid names preferred iupac name 3 4 5 trihydroxybenzoic acid other names gallic acid identifiers cas number 149 91 7 y 5995 86 8 monohydrate y 3d model jsmol interactive image chebi chebi 30778 y chembl chembl288114 y chemspider 361 y echa infocard 100 005 228 ec number 205 749 9 iuphar bps 5549 kegg c01424 y pubchem cid 370 rtecs number lw7525000 unii 632xd903sp y 48339473ot monohydrate y comptox dashboard epa dtxsid0020650 inchi inchi 1s c7h6o5 c8 4 1 3 7 11 12 2 5 9 6 4 10 h1 2 8 10h h 11 12 y key lnthitqwfmadlm uhfffaoysa n y inchi 1 c7h6o5 c8 4 1 3 7 11 12 2 5 9 6 4 10 h1 2 8 10h h 11 12 key lnthitqwfmadlm uhfffaoyan smiles o c o c1cc o c o c o c1 properties chemical formula c 7 h 6 o 5 molar mass 170 12 g mol appearance white yellowish white or pale fawn colored crystals density 1 694 g cm 3 anhydrous melting point 260 c 500 f 533 k solubility in water 1 19 g 100 ml 20 c anhydrous 1 5 g 100 ml 20 c monohydrate solubility soluble in alcohol ether glycerol acetone negligible in benzene chloroform petroleum ether log p 0 70 acidity p k a cooh 4 5 oh 10 magnetic susceptibility χ 90 0 10 6 cm 3 mol hazards occupational safety and health ohs osh main hazards irritant nfpa 704 fire diamond 1 0 lethal dose or concentration ld lc ld 50 median dose 5000 mg kg rabbit oral safety data sheet sds external msds related compounds related phenols carboxylic acids related compounds benzoic acid phenol pyrogallol except where otherwise noted data are given for materials in their standard state at 25 c 77 f 100 kpa n verify what is y n infobox references chemical compound gallic acid also known as 3 4 5 trihydroxybenzoic acid is a trihydroxybenzoic acid with the formula c 6 h 2 oh 3 co 2 h it is classified as a phenolic acid it is found in gallnuts sumac witch hazel tea leaves oak bark and other plants 1 it is a white solid although samples are typically brown owing to partial oxidation salts and esters of gallic acid are termed gallates its name is derived from oak galls which were historically used to prepare tannic acid despite the name gallic acid does not contain gallium isolation and derivatives edit electrostatic potential map of surface of gallic acid molecule ellagic acid 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 biphenyl and two cyclic ester links lactones forming two additional 6 piece cycles gallic acid is easily freed from gallotannins by acidic or alkaline hydrolysis when heated with concentrated sulfuric acid gallic acid converts to rufigallol 2 biosynthesis edit chemical structure of 3 5 didehydroshikimate gallic acid is formed from 3 dehydroshikimate by the action of the enzyme shikimate dehydrogenase to produce 3 5 didehydroshikimate this latter compound aromatizes 3 4 reactions edit oxidation and oxidative coupling edit alkaline solutions of gallic acid are readily oxidized by air the oxidation is catalyzed by the enzyme gallate dioxygenase an enzyme found in pseudomonas putida oxidative coupling of gallic acid with arsenic acid permanganate persulfate or iodine yields ellagic acid as does reaction of methyl gallate with iron iii chloride 5 gallic acid forms intermolecular esters depsides such as digallic and cyclic ether esters depsidones 5 hydrogenation edit hydrogenation of gallic acid gives the cyclohexane derivative hexahydrogallic acid 6 decarboxylation edit heating gallic acid gives pyrogallol 1 2 3 trihydroxybenzene this conversion is catalyzed by gallate decarboxylase esterification edit many esters of gallic acid are known both synthetic and natural gallate 1 beta glucosyltransferase catalyzes the glycosylation attachment of glucose of gallic acid historical context and uses edit gallic acid is an important component of iron gall ink the standard european writing and drawing ink from the 12th to 19th centuries with a history extending to the roman empire and the dead sea scrolls pliny the elder 23 79 ad describes the use of gallic acid as a means of detecting an adulteration of verdigris 7 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 tannic acid it could then be mixed with green vitriol ferrous sulfate obtained by allowing sulfate saturated water from a spring or mine drainage to evaporate citation needed and gum arabic from acacia trees this combination of ingredients produced the ink 8 gallic acid was one of the substances used by angelo mai 1782 1854 among other early investigators of palimpsests 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 9 gallic acid was first studied by the swedish chemist carl wilhelm scheele in 1786 10 in 1818 french chemist and pharmacist henri braconnot 1780 1855 devised a simpler method of purifying gallic acid from galls 11 gallic acid was also studied by the french chemist théophile jules pelouze 1807 1867 12 among others when mixed with acetic acid gallic acid had uses in early types of photography like the calotype to make the silver more sensitive to light it was also used in developing photographs 13 occurrence edit gallic acid is found in a number of land plants such as the parasitic plant cynomorium coccineum 14 the aquatic plant myriophyllum spicatum and the blue green alga microcystis aeruginosa 15 gallic acid is also found in various oak species 16 caesalpinia mimosoides 17 and in the stem bark of boswellia dalzielii 18 among others many foodstuffs contain various amounts of gallic acid especially fruits including strawberries grapes bananas 19 20 as well as teas 19 21 cloves 22 and vinegars 23 clarification needed carob fruit is a rich source of gallic acid 24 165 mg per 100 g 24 esters edit also known as galloylated esters methyl gallate ethyl gallate a food additive with e number e313 propyl gallate or propyl 3 4 5 trihydroxybenzoate an ester formed by the condensation of gallic acid and propanol octyl gallate the ester of octanol and gallic acid dodecyl gallate or lauryl gallate the ester of dodecanol and gallic acid epicatechin gallate a flavan 3 ol a type of flavonoid present in green tea epigallocatechin gallate egcg also known as epigallocatechin 3 gallate the ester of epigallocatechin and gallic acid and a type of catechin gallocatechin gallate gcg the ester of gallocatechin and gallic acid and a type of flavan 3ol theaflavin 3 gallate a theaflavin derivative gallate esters are antioxidants useful in food preservation with propyl gallate being the most commonly used their use in human health is scantly supported by evidence spectral data edit uv vis lambda max 220 271 nm ethanol spectrum of gallic acid extinction coefficient log ε ir major absorption bands ν 3491 3377 1703 1617 1539 1453 1254 cm 1 kbr nmr proton nmr acetone d6 d doublet dd doublet of doublets m multiplet s singlet δ 7 15 2h s h 3 and h 7 carbon 13 nmr acetone d6 δ 167 39 c 1 144 94 c 4 and c 6 137 77 c 5 120 81 c 2 109 14 c 3 and c 7 other nmr data ms masses of main fragments esi ms m h m z 169 0137 ms ms iontrap 35 ce m z product 125 100 81 1 17 see also edit benzoic acid catechol hydrolyzable tannin pyrogallol syringol syringaldehyde syringic acid shikimic acid references edit haslam e cai y 1994 plant polyphenols vegetable tannins gallic acid metabolism natural product reports 11 1 41 66 doi 10 1039 np9941100041 pmid 15206456 andrew pengelly 2004 the constituents of medicinal plants 2nd ed allen unwin pp 29 30 gallic acid pathway on metacyc org dewick pm haslam e 1969 phenol biosynthesis in higher plants gallic acid biochemical journal 113 3 537 542 doi 10 1042 bj1130537 pmc 1184696 pmid 5807212 1 2 edwin ritzer rudolf sundermann 2007 hydroxycarboxylic acids aromatic ullmann s encyclopedia of industrial chemistry 7th ed wiley p 6 albert w burgstahler and zoe j bithos 1962 hexahydrogallic acid and hexahydrogallic acid triacetate organic syntheses 42 62 doi 10 15227 orgsyn 042 0062 pliny the elder with john bostock and h t riley trans the natural history of pliny london england henry g bohn 1857 vol 6 p 196 in book 34 chapter 26 of his natural history pliny states that verdigris a form of copper acetate cu ch 3 coo 2 2cu oh 2 which was used to process leather was sometimes adulterated with copperas a form of iron ii sulfate feso 4 7h 2 o he presented a simple test for determining the purity of verdigris from p 196 the adulteration of verdigris 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 fruen lois iron gall ink archived from the original on 2011 10 02 l d reynolds and n g wilson scribes and scholars 3rd ed oxford 1991 pp 193 4 carl wilhelm scheele 1786 om sal essentiale gallarum eller gallåple salt on the essential salt of galls or gall salt kongliga vetenskaps academiens nya handlingar proceedings of the royal swedish academy of science 7 30 34 braconnot henri 1818 observations sur la préparation et la purification de l acide gallique et sur l existence d un acide nouveau dans la noix de galle observations on the preparation and purification of gallic acid and on the existence of a new acid in galls annales de chimie et de physique 9 181 184 j pelouze 1833 mémoire sur le tannin et les acides gallique pyrogallique ellagique et métagallique annales de chimie et de physique 54 337 365 presented february 17 1834 taylor roger schaaf larry john 2007 impressed by light british photographs from paper negatives 1840 1860 metropolitan museum of art isbn 978 1 58839 225 1 zucca paolo rosa antonella tuberoso carlo piras alessandra rinaldi andrea sanjust enrico dessì maria rescigno antonio 11 january 2013 evaluation of antioxidant potential of maltese mushroom cynomorium coccineum by means of multiple chemical and biological assays nutrients 5 1 149 161 doi 10 3390 nu5010149 pmc 3571642 pmid 23344249 nakai s 2000 myriophyllum spicatum released allelopathic polyphenols inhibiting growth of blue green algae microcystis aeruginosa water research 34 11 3026 3032 bibcode 2000watre 34 3026n doi 10 1016 s0043 1354 00 00039 7 mämmelä pirjo savolainen heikki lindroos lasse kangas juhani vartiainen terttu 2000 analysis of oak tannins by liquid chromatography electrospray ionisation mass spectrometry journal of chromatography a 891 1 75 83 bibcode 2000jcha 891 75m doi 10 1016 s0021 9673 00 00624 5 pmid 10999626 1 2 chanwitheesuk anchana teerawutgulrag aphiwat kilburn jeremy d rakariyatham nuansri 2007 antimicrobial gallic acid from caesalpinia mimosoides lamk food chemistry 100 3 1044 1048 bibcode 2007foodc 100 1044c doi 10 1016 j foodchem 2005 11 008 alemika taiwo e onawunmi grace o olugbade tiwalade a 2007 antibacterial phenolics from boswellia dalzielii nigerian journal of natural products and medicine 10 1 108 10 1 2 pandurangan ak mohebali n norhaizan me looi cy 2015 gallic acid attenuates dextran sulfate sodium induced experimental colitis in balb c mice drug design development and therapy 9 3923 34 doi 10 2147 dddt s86345 pmc 4524530 pmid 26251571 koyama k goto yamamoto n hashizume k 2007 influence of maceration temperature in red wine vinification on extraction of phenolics from berry skins and seeds of grape vitis vinifera bioscience biotechnology and biochemistry 71 4 958 65 bibcode 2007bsbtb 71 958k doi 10 1271 bbb 60628 pmid 17420579 hodgson jm morton lw puddey ib beilin lj croft kd 2000 gallic acid metabolites are markers of black tea intake in humans journal of agricultural and food chemistry 48 6 2276 80 bibcode 2000jafc 48 2276h doi 10 1021 jf000089s pmid 10888536 pathak s b niranjan k padh h rajani m et al 2004 tlc densitometric method for the quantification of eugenol and gallic acid in clove chromatographia 60 3 4 241 244 doi 10 1365 s10337 004 0373 y s2cid 95396304 gálvez miguel carrero barroso carmelo garcía pérez bustamante juan antonio 1994 analysis of polyphenolic compounds of different vinegar samples zeitschrift für lebensmittel untersuchung und forschung 199 29 31 doi 10 1007 bf01192948 s2cid 91784893 goulas vlasios stylos evgenios chatziathanasiadou maria mavromoustakos thomas tzakos andreas 10 november 2016 functional components of carob fruit linking the chemical and biological space international journal of molecular sciences 17 11 1875 bibcode 2016ijmsc 17 1875g doi 10 3390 ijms17111875 issn 1422 0067 pmc 5133875 pmid 27834921 v t e types of gallotannins aglycones digallic acid gallic acid galloylglucoses monogalloylglucoses 1 galloylglucose glucogallin digalloylglucoses 1 6 digalloylglucose 2 6 digalloylglucose 3 6 digalloylglucose trigalloylglucoses 1 2 3 trigalloylglucose 1 2 3 tri o galloyl β d glucose 1 2 6 trigalloylglucose 1 3 6 trigalloylglucose tetragalloylglucoses 1 2 3 6 tetragalloylglucose 1 2 3 6 tetrakis o galloyl β d glucose 1 2 4 6 tetragalloylglucose 1 2 4 6 tetrakis o galloyl β d glucose pentagalloylglucoses 1 2 3 4 6 pentagalloylglucose 6 digalloyl 1 2 3 trigalloylglucose other hexagalloylglucose heptagalloylglucose octagalloylglucose nonagalloylglucose decagalloylglucose galloylquinic acids monogalloylquinic acids 3 o galloylquinic acid theogallin 4 o galloylquinic acid 5 o galloylquinic acid digalloylquinic acids 1 4 di o galloylquinic acid 3 4 di o galloylquinic acid 3 5 di o galloylquinic acid 4 5 di o galloylquinic acid trigalloylquinic acids 1 3 4 tri o galloylquinic acid 3 4 5 tri o galloylquinic acid galloylshikimic acids 4 o galloylshikimic acid 5 o galloylshikimic acid 3 5 di o galloylshikimic acid 3 4 5 tri o galloylshikimic acid others 1 2 6 trigalloylalloside 1 3 6 trigalloylalloside 1 2 3 6 tetragalloylalloside 1 o galloylquercitol 1 4 di o galloylquercitol v t e phenolic acids c6 c1 and their glycosides monohydroxybenzoic acids 3 hydroxybenzoic acid 4 hydroxybenzoic acid salicylic acid 2 hydroxybenzoic acid glycosides p hydroxybenzoic acid glucoside alkylated methylparaben methyl p hydroxybenzoic acid dihydroxybenzoic acids 2 3 dihydroxybenzoic acid hypogallic acid 2 4 dihydroxybenzoic acid 2 5 dihydroxybenzoic acid gentisic acid 2 6 dihydroxybenzoic acid 3 4 dihydroxybenzoic acid protocatechuic acid 3 5 dihydroxybenzoic acid alkylated ethyl protocatechuate orsellinic acid trihydroxybenzoic acids gallic acid phlorogluci...