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G7384 Sigma

Gallic acid

97.5-102.5% (titration)

Synonym: 3,4,5-Trihydroxybenzoic acid

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Description

Biochem/physiol Actions

Gallic acid is a water soluble phenolic acid present in grapes and in the leaves of many plants. Gallic acid esters, such as tannins, catechin gallates and aliphatic gallates are potent antioxidants in vitro. However, gallic acid itself also appears to have antioxidant, anticarcinogenic and antiangiogenic activity in vitro.

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1 kg in poly bottle

100, 250 g in poly bottle

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xi
Risk Statements (Europe) 
Safety Statements (Europe) 
26-36
WGK Germany 
2
RTECS 
LW7525000

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Peer-Reviewed Papers

References

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Gallic acid causes inactivating phosphorylation of cdc25A/cdc25C-cdc2 via ATM-Chk2 activation, leading to cell cycle arrest, and induces apoptosis in human prostate carcinoma DU145 cells. Agarwal, C., et al. Mol. Cancer Ther. 5, 3294-3302, (2006)

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Gallic acid is partially responsible for the antiangiogenic activities of Rubus leaf extract. Liu, Z., et al. Phytother Res. 20, 806-813, (2006)

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Gallic acid, an antioxidant, exhibits antiapoptotic potential in normal human lymphocytes: A Bcl-2 independent mechanism. Sohi, K.K., et al. J. Nutr. Sci. Vitaminol. 49, 221-227, (2003)

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Chlorogenic acid, quercetin-3-rutinoside and black tea phenols are extensively metabolized in humans. Olthof MR, Hollman PC, Buijsman MN, et al. J. Nutr. 133(6), 1806-14, (2003)

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Bioavailability and catabolism of green tea flavan-3-ols in humans. Del Rio D, Calani L, Cordero C, et al. Nutrition 26(11-12), 1110-6, (2010)

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A metabolite profiling approach to identify biomarkers of flavonoid intake in humans. Loke, W.M., et al. J. Nucl. Med. 139, 2309-14, (2009)

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Gallic acid interacts with α-synuclein to prevent the structural collapse necessary for its aggregation. Liu Y, Carver JA, Calabrese AN, et al. Biochim. Biophys. Acta 1844(9), 1481-5, (2014)

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Evaluation of gallic acid loaded zein sub-micron electrospun fibre mats as novel active packaging materials. Neo YP, Swift S, Ray S, et al. Food Chem. 141(3), 3192-200, (2013)

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Bioavailability of multiple components following acute ingestion of a polyphenol-rich juice drink. Borges G, Mullen W, Mullan A, et al. Mol. Nutr. Food. Res. 54 Suppl 2, S268-77, (2010)

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SPE-NMR metabolite sub-profiling of urine. Jacobs DM, Spiesser L, Garnier M, et al. Anal. Bioanal. Chem 404(8), 2349-61, (2012)

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Grape seed extract has superior beneficial effects than vitamin E on oxidative stress and apoptosis in the hippocampus of streptozotocin induced diabetic rats. Yonguc GN, Dodurga Y, Adiguzel E, et al. Gene 555(2), 119-26, (2015)

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Gallic acid regulates body weight and glucose homeostasis through AMPK activation. Doan KV, Ko CM, Kinyua AW, et al. Endocrinology 156(1), 157-68, (2015)

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[Simultaneous determination of gallic acid and hesperidin contained in Xiaogu capsule by HPLC]. Lin FF, Xie WB, Yu J, et al. Zhongguo Zhong Yao Za Zhi 38(10), 1518-20, (2013)

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Oral treatment with gallic acid and quercetin alleviates lindane-induced cardiotoxicity in rats. Vijaya Padma V, Poornima P, Prakash C, et al. Can. J. Physiol. Pharmacol. 91(2), 134-40, (2013)

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In vitro inhibition of ?-carbonic anhydrase isozymes by some phenolic compounds. Sevim Beyza Oztürk Sarikaya et al Bioorg. Med. Chem. Lett. 21, 4259-62, (2011)

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Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Alessio Innocenti et al Bioorg. Med. Chem. 18, 2159-64, (2010)

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Neuroprotective effects of oral gallic acid against oxidative stress induced by 6-hydroxydopamine in rats. Mansouri MT, Farbood Y, Sameri MJ, et al. Food Chem. 138(2-3), 1028-33, (2013)

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Pharmacokinetics of gallic acid and its relative bioavailability from tea in healthy humans. Shahrzad S, Aoyagi K, Winter A, et al. J. Nutr. 131(4), 1207-10, (2001)

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Plant polyphenols (vegetable tannins): gallic acid metabolism. Haslam E and Cai Y Nat. Prod. Rep. 11(1), 41-66, (1994)

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Chemical constituents of the fruits of Morinda citrifolia (Noni) and their antioxidant activity. Bao-Ning Su et al J. Nat. Prod. 68, 592-5, (2005)

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Dentin biomodification potential depends on polyphenol source. Aguiar TR, Vidal CM, Phansalkar RS, et al. J. Dent. Res. 93(4), 417-22, (2014)

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Synthesis and structure-activity relationship study of antidiabetic penta-O-galloyl-D-glucopyranose and its analogues. Yulin Ren et al J. Med. Chem. 49, 2829-37, (2006)

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Gallic acid and gallic acid derivatives: effects on drug metabolizing enzymes. Ow YY and Stupans I Curr. Drug Metab. 4(3), 241-8, (2003)

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Bioactive compounds from culinary herbs inhibit a molecular target for type 2 diabetes management, dipeptidyl peptidase IV. Bower AM, Real Hernandez LM, Berhow MA, et al. J. Agric. Food Chem. 62(26), 6147-58, (2014)

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The sensitizing capacity of the antioxidants propyl, octyl, and dodecyl gallate and some related gallic acid esters. Hausen BM and Beyer W Contact Dermatitis 26(4), 253-8, (1992)

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Dihydro-beta-agarofuran sesquiterpenes and pentacyclic triterpenoids from the root bark of Osyris lanceolata. Elizabeth M O Yeboah et al J. Nat. Prod. 73, 1151-5, (2010)

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Polyphenolic constituents of Actaea racemosa. Paiboon Nuntanakorn et al J. Nat. Prod. 69, 314-8, (2006)

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Benzophenones and biflavonoids from Rheedia edulis. Ulyana Muñoz Acuña et al J. Nat. Prod. 73, 1775-9, (2010)

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Synthesis of some novel pyrazolo[3,4-b]pyridine and pyrazolo[3,4-d]pyrimidine derivatives bearing 5,6-diphenyl-1,2,4-triazine moiety as potential antimicrobial agents. Tarik El-Sayed Ali et al Eur. J. Med. Chem. 44, 4385-92, (2009)

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QSAR study of antioxidant activity of wine polyphenols. Vesna Rastija et al Eur. J. Med. Chem. 44, 400-8, (2009)

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Polyphenol levels in human urine after intake of six different polyphenol-rich beverages. Ito H, Gonthier MP, Manach C, et al. Br. J. Nutr. 94(4), 500-9, (2005)

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Development of a generic assay for the determination of total trihydroxybenzoate derivatives based on gold-luminol chemiluminescence. Giokas DL, Christodouleas DC, Vlachou I, et al. Anal. Chim. Acta 764, 70-7, (2013)

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Maplexins, new ?-glucosidase inhibitors from red maple (Acer rubrum) stems. Chunpeng Wan et al Bioorg. Med. Chem. Lett. 22, 597-600, (2012)

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Alkyl esters of gallic acid as anticancer agents: a review. Locatelli C, Filippin-Monteiro FB, and Creczynski-Pasa TB Eur. J. Med. Chem. 60, 233-9, (2013)

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Tea catechins inhibit hepatocyte growth factor receptor (MET kinase) activity in human colon cancer cells: kinetic and molecular docking studies. Christine A Larsen et al J. Med. Chem. 52, 6543-5, (2009)

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Phloroglucinol glycosides from the fresh fruits of Eucalyptus maideni. Li-Wen Tian et al J. Nat. Prod. 73, 160-3, (2010)

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Inhibition of aldose reductase from cataracted eye lenses by finger millet (Eleusine coracana) polyphenols. S Chethan et al Bioorg. Med. Chem. 16, 10085-90, (2008)

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Gallic acid: molecular rival of cancer. Verma S, Singh A, and Mishra A Environ. Toxicol. Pharmacol. 35(3), 473-85, (2013)

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Explicit role of peroxisome proliferator-activated receptor gamma in gallic acid-mediated protection against ischemia-reperfusion-induced acute kidney injury in rats. Singh JP, Singh AP, and Bhatti R J. Surg. Res. 187(2), 631-9, (2014)

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Rapid and specific sensing of gallic acid with a photoelectrochemical platform based on polyaniline-reduced graphene oxide-TiO2. Ma W, Han D, Gan S, et al. Chem. Commun. (Camb.) 49(71), 7842-4, (2013)

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Ester derivatives of gallic acid with potential toxicity toward L1210 leukemia cells. Claudriana Locatelli et al Bioorg. Med. Chem. 16, 3791-9, (2008)

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The anthocyanin metabolites gallic acid, 3-O-methylgallic acid, and 2,4,6-trihydroxybenzaldehyde decrease human colon cancer cell viability by regulating pro-oncogenic signals. Forester SC, Choy YY, Waterhouse AL, et al. Mol. Carcinog. 53(6), 432-9, (2014)

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Application of surface enzyme treatments using laccase and a hydrophobic compound to paper-based media. Cusola O, Valls C, Vidal T, et al. Bioresour. Technol. 131, 521-6, (2013)

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Synthesis and antioxidant properties of pulvinic acids analogues. Brice Nadal et al Bioorg. Med. Chem. 18, 7931-9, (2010)

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Antioxidant and antihypertensive activity of extract from Thymus serpyllum L. in experimental hypertension. Mihailovic-Stanojevic N, Belščak-Cvitanović A, Grujić-Milanović J, et al. Plant Foods Hum. Nutr. 68(3), 235-40, (2013)

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Pu-erh tea hot-water extract activates Akt and induces insulin-independent glucose transport in rat skeletal muscle. Ma X, Tsuda S, Yang X, et al. J. Med. Food 16(3), 259-62, (2013)

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Antitumor activity of methyl gallate by inhibition of focal adhesion formation and Akt phosphorylation in glioma cells. Lee SH, Kim JK, Kim DW, et al. Biochim. Biophys. Acta 1830(8), 4017-29, (2013)

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Pyrogallol and its analogs can antagonize bacterial quorum sensing in Vibrio harveyi. Nanting Ni et al Bioorg. Med. Chem. Lett. 18, 1567-72, (2008)

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Evidence does not support a role for gallic acid in Phragmites australis invasion success. Weidenhamer JD, Li M, Allman J, et al. J. Chem. Ecol. 39(2), 323-32, (2013)

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Studies on the chemical constituents and anticancer activity of Saxifraga stolonifera (L) Meeb. Zhuo Chen et al Bioorg. Med. Chem. 16, 1337-44, (2008)

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Phenolic glycosides from berries of Pimenta dioica. Hiroe Kikuzaki et al J. Nat. Prod. 71, 861-5, (2008)

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Rational Design of Novel, Potent Small Molecule Pan-Selectin Antagonists Kranich, R.; et al. J. Med. Chem. 50, 1101-1115, (2007)

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Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi. P C Leal et al Bioorg. Med. Chem. Lett. 19, 1793-6, (2009)

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Biopesticides from plants: Calceolaria integrifolia s.l. Céspedes CL, Salazar JR, Ariza-Castolo A, et al. Environ. Res. 132, 391-406, (2014)

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Changes of antioxidant activity and formation of 5-hydroxymethylfurfural in honey during thermal and microwave processing. Kowalski S Food Chem. 141(2), 1378-82, (2013)

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In vitro polyphenolics erythrocyte model and in vivo chicken embryo model revealed gallic acid to be a potential hemorrhage inducer: physicochemical action mechanisms. Ker YB, Peng CC, Lin CH, et al. Chem. Res. Toxicol. 26(3), 325-35, (2013)

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Proton dissociation is important to understanding structure-activity relationships of gallic acid antioxidants. Hong-Fang Ji et al Bioorg. Med. Chem. Lett. 16, 4095-8, (2006)

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Gallic acid provokes DNA damage and suppresses DNA repair gene expression in human prostate cancer PC-3 cells. Liu KC, Ho HC, Huang AC, et al. Environ. Toxicol. 28(10), 579-87, (2013)

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Urinary excretion of 13 dietary flavonoids and phenolic acids in free-living healthy subjects - variability and possible use as biomarkers of polyphenol intake. Mennen LI, Sapinho D, Ito H, et al. Eur. J. Clin. Nutr. 62(4), 519-25, (2008)

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Surfactants, aromatic and isoprenoid compounds, and fatty acid biosynthesis inhibitors suppress Staphylococcus aureus production of toxic shock syndrome toxin 1. Peter J McNamara et al Antimicrob. Agents Chemother. 53, 1898-906, (2009)

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Structures and radical-scavenging activities of phenolic constituents from the bark of Picea jezoensis var. jezoensis. Shun-ichi Wada et al J. Nat. Prod. 70, 1605-10, (2007)

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Catechins are not major components responsible for the beneficial effect of Camellia sinensis on the ovarian δ-ALA-D activity inhibited by cadmium. Soares MB, Izaguirry AP, Vargas LM, et al. Food Chem. Toxicol. 55, 463-9, (2013)

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Discovery of estrogen receptor ? modulators from natural compounds in Si-Wu-Tang series decoctions using estrogen-responsive MCF-7 breast cancer cells. Li Liu et al Bioorg. Med. Chem. Lett. 22, 154-63, (2012)

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Antifungal activity of gallic acid purified from Terminalia nigrovenulosa bark against Fusarium solani. Nguyen DM, Seo DJ, Lee HB, et al. Microb. Pathog. 56, 8-15, (2013)

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New diterpenoids and the bioactivity of Erythrophleum fordii. Chuan-Chung Tsao et al Bioorg. Med. Chem. 16, 9867-70, (2008)

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Molecular hairpin: a possible model for inhibition of tau aggregation by tannic acid. Yao J, Gao X, Sun W, et al. Biochemistry 52(11), 1893-902, (2013)

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Simultaneous determination and pharmacokinetic study of stachydrine and leonurine in rat plasma after oral administration of Herba Leonuri extract by LC-MS/MS. Li B, Wu J, and Li X J. Pharm. Biomed. Anal. 76, 192-9, (2013)

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Synthesis and antioxygenic activities of seabuckthorn flavone-3-ols and analogs. N Pandurangan et al Bioorg. Med. Chem. Lett. 21, 5328-30, (2011)

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Differentiation between stoichiometric and anticatalytic antioxidant properties of benzoic acid analogues: a structure/redox potential relationship study. Franck T, Mouithys-Mickalad A, Robert T, et al. Chem. Biol. Interact. 206(2), 194-203, (2013)

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Antioxidant capacities, phenolic contents, and GC/MS analysis of Rhodiola imbricata Edgew. root extracts from Trans-Himalaya. Tayade AB, Dhar P, Sharma M, et al. J. Food Sci. 78(3), C402-10, (2013)

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IAPP aggregation and cellular toxicity are inhibited by 1,2,3,4,6-penta-O-galloyl-β-D-glucose. Bruno E, Pereira C, Roman KP, et al. Amyloid 20(1), 34-8, (2013)

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Inhibitory effect of macabarterin, a polyoxygenated ellagitannin from Macaranga barteri, on human neutrophil respiratory burst activity. Rostand Manfouo Ngoumfo et al J. Nat. Prod. 71, 1906-10, (2008)

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Allelopathic effects of gallic acid from Aegiceras corniculatum on Cyclotella caspia. Liu Y, Li F, and Huang Q J. Environ. Sci. (China) 25(4), 776-84, (2013)

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Green tea from purple leaf coloured tea clones in Kenya- their quality characteristics. Kilel EC, Faraj AK, Wanyoko JK, et al. Food Chem. 141(2), 769-75, (2013)

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Tylosema esculentum extractives and their bioactivity. Ofentse Mazimba et al Bioorg. Med. Chem. 19, 5225-30, (2011)

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Anti-babesial and anti-plasmodial compounds from Phyllanthus niruri. Subeki Subeki et al J. Nat. Prod. 68, 537-9, (2005)

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Synthesis and biological evaluation of nitrogen-containing benzophenone analogues as TNF-alpha and IL-6 inhibitors with antioxidant activity. Babasaheb P Bandgar et al Bioorg. Med. Chem. Lett. 20, 2292-6, (2010)

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Gallic acid modulates cerebral oxidative stress conditions and activities of enzyme-dependent signaling systems in streptozotocin-treated rats. Kade IJ and Rocha JB Neurochem. Res. 38(4), 761-71, (2013)

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Anti-inflammatory and anti-allergic activities of Pentaherb formula, Moutan Cortex (Danpi) and gallic acid. Liu KY, Hu S, Chan BC, et al. Molecules 18(3), 2483-500, (2013)

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Antimicrobial and antioxidant activities of Cichorium intybus root extract using orthogonal matrix design. Liu H, Wang Q, Liu Y, et al. J. Food Sci. 78(2), M258-63, (2013)

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Kinetics of the transformation of n-propyl gallate and structural analogs in the perfused rat liver. Eler GJ, Santos IS, de Moraes AG, et al. Toxicol. Appl. Pharmacol. 273(1), 35-46, (2013)

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Inhibition of 15-lipoxygenase-catalysed oxygenation of arachidonic acid by substituted benzoic acids. Wendy R Russell et al Bioorg. Med. Chem. 16, 4589-93, (2008)

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Leonurus japonicus, Leonurus cardiaca, Leonotis leonurus: a novel HPLC study on the occurrence and content of the pharmacologically active guanidino derivative leonurine. Kuchta K, Ortwein J, and Rauwald HW Pharmazie 67(12), 973-9, (2012)

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Synthesis of 3-O-methylgallic acid a powerful antioxidant by electrochemical conversion of syringic acid. Gargouri OD, Gargouri B, Trabelsi SK, et al. Biochim. Biophys. Acta 1830(6), 3643-9, (2013)

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Antiradical activity of gallic acid included in lipid interphases. Salcedo CL, Frías MA, Cutro AC, et al. Biochim. Biophys. Acta 1838(10), 2656-61, (2014)

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Evaluation of antioxidant potential of “maltese mushroom” (Cynomorium coccineum) by means of multiple chemical and biological assays. Zucca P, Rosa A, Tuberoso CI, et al. Nutrients 5(1), 149-61, (2013)

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Preparation, characterization and in vitro release study of gallic acid loaded silica nanoparticles for controlled release. Hu H, Nie L, Feng S, et al. Pharmazie 68(6), 401-5, (2013)

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Total phenolic content and antioxidative properties of commercial tinctures obtained from some Lamiaceae plants. Kowalczyk A, Biskup I, and Fecka I Nat. Prod. Commun. 7(12), 1631-4, (2012)

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Dietary intake of phytonutrients in relation to fruit and vegetable consumption in Korea. Lee HS, Cho YH, Park J, et al. J. Acad. Nutr. Diet. 113(9), 1194-9, (2013)

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A novel phenolic compound from Phyllanthus emblica. She G, Cheng R, Sha L, et al. Nat. Prod. Commun. 8(4), 461-2, (2013)

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Two new glycosides from Carduus acanthoides. Liu SK, Que S, Cheng W, et al. J. Asian Nat. Prod. Res. 15(12), 1243-8, (2013)

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in vitro study of the PLA2 inhibition and antioxidant activities of Aloe vera leaf skin extracts. Maher Kammoun et al Lipids Health Dis. 10, 30, (2011)

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Gallic acid selectively induces the necrosis of activated hepatic stellate cells via a calcium-dependent calpain I activation pathway. Hsieh SC, Wu CH, Wu CC, et al. Life Sci. 102(1), 55-64, (2014)

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Syringic acid from Tamarix aucheriana possesses antimitogenic and chemo-sensitizing activities in human colorectal cancer cells. Abaza MS, Al-Attiyah R, Bhardwaj R, et al. Pharm. Biol. 51(9), 1110-24, (2013)

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Use of pyrogallol red and pyranine as probes to evaluate antioxidant capacities towards hypochlorite. Pérez-Cruz F, Cortés C, Atala E, et al. Molecules 18(2), 1638-52, (2013)

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(+)-rumphiin and polyalthurea, new compounds from the stems of Polyalthia rumphii. Wang TS, Luo YP, Wang J, et al. Nat. Prod. Commun. 8(10), 1427-9, (2013)

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Free radical scavenging and total antioxidant capacity of root extracts of Anchomanes difformis Engl. (Araceae). Aliyu AB, Ibrahim MA, Musa AM, et al. Acta Pol. Pharm. 70(1), 115-21, (2013)

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Investigation into biologically active constituents of Geum rivale L. Owczarek A and Gudej J Acta Pol. Pharm. 70(1), 111-4, (2013)

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Statistical optimization of bioprocess parameters for enhanced gallic acid production from coffee pulp tannins by Penicillium verrucosum. Bhoite RN, Navya PN, and Murthy PS Prep Biochem Biotechnol. 43(4), 350-63, (2013)

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Healing effect of hydro-alcoholic extract of Ephedra pachyclada Boiss. in experimental gastric ulcer in rat. Pirbalouti AG, Amirmohammadi M, Azizi S, et al. Acta Pol. Pharm. 70(6), 1003-9, (2013)

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Merck 14,4345

Beil. 10,IV,1993

Aldrich MSDS 1, 986:D / Corp MSDS 1 (1), 1760:D / FT-IR 2 (2), 2713:B / FT-IR 1 (2), 232:A / FT-NMR 1 (2), 1147:C / IR-Spectra (3), 980:D / IR-Spectra (2), 859:B / NMR-Reference 2 (2), 228:C / RegBook 1 (2), 1821:B / Sax 6, 1469 / Sigma FT-IR 1 (2), 589:A / Structure Index 1, 291:D:6

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