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W294705 Aldrich

Propyl gallate

≥98%, FCC

Synonym: 3,4,5-Trihydroxybenzoic acid propyl ester

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Properties

Related Categories Alphabetical Listings, Flavors and Fragrances, Halal Certified Products, Kosher Certified Products, O - Z,
biological source   synthetic
grade   Halal
  Kosher
reg. compliance   FCC
  FDA 21 CFR (172.615)
  FDA 21 CFR (175.125)
  FDA 21 CFR (175.300)
  FDA 21 CFR (175.380)
  FDA 21 CFR (175.390)
  EU Regulation 1334/2008 & 178/2002
  EU Regulation 178/2002
assay   ≥98%
mp   146-149 °C(lit.)
Organoleptic   odorless
allergen   no known allergens

Description

Packaging

1 kg in poly bottle

10 kg in fiber drum

Reconstitution

Prepare a 0.1M solution in glycerol:PBS (9:1)

Application

Used as an anti-fade reagent in fluorescence microscopy to reduce photobleaching of fluorescent probes such as rhodamine and fluorescein.

Biochem/physiol Actions

An antioxidant that exhibits antimicrobial activity. Propyl gallate has been reported to be an effective antioxidant-based hepatoprotector, both in vitro and in vivo. It has also been shown to prevent neuronal apoptosis and block the death of neurons exposed to FeSO4/GA as well as partially protect endothelial cells against TNF-induced apoptosis. However, propyl gallate induced single strand breaks in DNA at concentrations higher than 0.25 μM when it was combined with copper concentrations at 5 μM and above. Another report, however, found that incubation of isolated rat hepatocytes with propyl gallate at concentrations of >1 mM induced cell killing, whereas, a lower concentration of propyl gallate > 0.5 mM resulted in a ladder formation of soluble low-molecular weight DNA fragments, characteristic of apoptosis.

An antioxidant that exhibits antimicrobial activity. Propyl gallate has been reported to be an effective antioxidant-based hepatoprotector, both in vitro and in vivo. It has also been shown to prevent neuronal apoptosis and block the death of neurons exposed to FeSO4/GA as well as partially protect endothelial cells against TNF-induced apoptosis.

Other Notes

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Price and Availability

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United States Pharmacopeia (USP) Reference Standard

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European Pharmacopoeia (EP) Reference Standard

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xn
Risk Statements (Europe) 
Safety Statements (Europe) 
24-37
WGK Germany 
2
RTECS 
LW8400000
Flash Point(F) 
368.6 °F
Flash Point(C) 
187 °C

Protocols & Articles

Articles

Understanding the Complexities of Kosher Ingredients

Dr. Luke Grocholl, Quality Assurance Supervisor, Sigma-Aldrich Flavors & Fragrances and Rabbi Gershon Segal
Keywords: Fermentation, Food & Beverage, Safety industry

Peer-Reviewed Papers

References

Set your institution to view full text papers.

DNA strand break induction and enhanced cytotoxicity of propyl gallate in the presence of copper(II). Jacobi, H., et al. Free Radic. Biol. Med. 24, 972-978, (1998)

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Astrocytic gap junctional communication decreases neuronal vulnerability to oxidative stress-induced disruption of Ca2+ homeostasis and cell death. Blanc, E.M., et al. J. Neurochem. 70, 958-970, (1998)

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Propyl gallate-induced DNA fragmentation in isolated rat hepatocytes. Nakagawa, Y., et al. Arch. Toxicol. 72, 33-37, (1997)

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Mitochondrial manganese superoxide dismutase prevents neural apoptosis and reduces ischemic brain injury. Keller, J.N., et al. J. Neurosci. 18, 687-697, (1998)

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Linoleic acid potentiates TNF-mediated oxidative stress, disruption of calcium homeostasis, and apoptosis of cultured vascular endothelial cells. Toborek, M., et al. J. Lipid Res. 38, 2155-2167, (1997)

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Propyl gallate as a hepatoprotector in vitro and in vivo. Wu, T.W., et al. Biochem. Pharmacol. 48, 419-422, (1994)

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Fluorescence microscopy: Reduced photobleaching of rhodamine and fluorescein protein conjugates by n-propyl gallate. Giloh, H., and Sedat, J.W. Science 217, 1252-1255, (1982)

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Anti-oxidant and anti-bacterial activities of novel N'-arylmethylidene-2-(3, 4-dimethyl-5, 5-dioxidopyrazolo[4,3-c][1,2]benzothiazin-2(4H)-yl) acetohydrazides. Matloob Ahmad et al Eur. J. Med. Chem. 45, 698-704, (2010)

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Evaluation of longevity enhancing compounds against transactive response DNA-binding protein-43 neuronal toxicity. Tauffenberger A, Julien C, and Parker JA Neurobiol. Aging 34(9), 2175-82, (2013)

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Differential role of ethylene and hydrogen peroxide in dark-induced stomatal closure. Kar RK, Parvin N, and Laha D Pak. J. Biol. Sci. 16(24), 1991-6, (2013)

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[Mechanism of the reduction of cerebral ischemic-reperfusion injury through inhibiting the activity of NF-kappaB by propyl gallate]. Zheng JM, Chen XC, Lin M, et al. Yao Xue Xue Bao 46(2), 158-64, (2011)

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Anti-oxidant, anti-fungal and anti-leishmanial activities of novel 3-[4-(1H-imidazol-1-yl) phenyl]prop-2-en-1-ones. Tanvir Hussain et al Eur. J. Med. Chem. 44, 4654-60, (2009)

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Effects of n-propyl gallate on neuronal survival after forebrain ischemia in rats. Kawano Y, Kawaguchi M, Hirota K, et al. Resuscitation 83(2), 249-52, (2012)

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Synthesis, antioxidant activities and urease inhibition of some new 1,2,4-triazole and 1,3,4-thiadiazole derivatives. Imtiaz Khan et al Eur. J. Med. Chem. 45, 5200-7, (2010)

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Effect of antioxidant inclusion and oil quality on broiler performance, meat quality, and lipid oxidation. Tavárez MA, Boler DD, Bess KN, et al. Poult. Sci. 90(4), 922-30, (2011)

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Ectromelia virus BTB/kelch proteins, EVM150 and EVM167, interact with cullin-3-based ubiquitin ligases. Brianne A. Wilton et al Virology 374, 82-99, (2008)

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2-Styrylchromones: novel strong scavengers of reactive oxygen and nitrogen species. Ana Gomes et al Bioorg. Med. Chem. 15, 6027-36, (2007)

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Loss Of Modifier Of Cell Adhesion Reveals A Pathway Leading To Axonal Degeneration. Chen, Q., et al. J. Neurosci. 29, 118-30, (2009)

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Role of redox signaling regulation in propyl gallate-induced apoptosis of human leukemia cells. Chen CH, Lin WC, Kuo CN, et al. Food Chem. Toxicol. 49(2), 494-501, (2011)

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Cryptococcus neoformans capsular enlargement and cellular gigantism during Galleria mellonella infection. García-Rodas R PLoS ONE 6(9), e24485, (2011)

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Effects of emulsifier hydrophile-lipophile balance and emulsifier concentration on the distributions of gallic acid, propyl gallate, and α-tocopherol in corn oil emulsions. Losada-Barreiro S, Sánchez-Paz V, and Bravo-Díaz C J. Colloid. Interface Sci. 389(1), 1-9, (2013)

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Oxidative stability of cooked, frozen, reheated beef patties: effect of antioxidants. Colindres P and Brewer MS J. Sci. Food Agric. 91(5), 963-8, (2011)

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Effects of a dietary antioxidant blend and vitamin E on growth performance, oxidative status, and meat quality in broiler chickens fed a diet high in oxidants. Lu T, Harper AF, Zhao J, et al. Poult. Sci. 93(7), 1649-57, (2014)

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Antioxidants modulate molecular mobility, oxygen permeability, and microstructure in zein films. Liang J and Ludescher RD J. Agric. Food Chem. 59(24), 13173-80, (2011)

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A target analogue imprinted polymer for the recognition of antiplatelet active ingredients in Radix Salviae Miltiorrhizae by LC/MS/MS. Huang M, Pang W, Zhang J, et al. J. Pharm. Biomed. Anal. 58, 12-8, (2012)

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Cloud-point extraction and reversed-phase high-performance liquid chromatography for the determination of synthetic phenolic antioxidants in edible oils. Chen M, Xia Q, Liu M, et al. J. Food Sci. 76(1), C98-103, (2011)

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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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Evidence on the formation of singlet oxygen in the donor side photoinhibition of photosystem II: EPR spin-trapping study. Yadav DK and Pospíšil P PLoS ONE 7(9), e45883, (2012)

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Cytological evaluation of the effect of azoxystrobin and alternative oxidase inhibitors in Botrytis cinerea. Inoue K, Tsurumi T, Ishii H, et al. FEMS Microbiol. Lett. 326(1), 83-90, (2012)

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Lipocarbazoles, secondary metabolites from Tsukamurella pseudospumae Acta 1857 with antioxidative activity. Kathrin Schneider et al J. Nat. Prod. 72, 1768-72, (2009)

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Improvement of aminolevulinic acid (ALA)-mediated photodynamic diagnosis using n-propyl gallate. Hirano T, Hagiya Y, Fukuhara H, et al. Photodiagnosis Photodyn. Ther. 10(1), 28-32, (2013)

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Bioactive constituents from Boswellia papyrifera. Atta-ur-Rahman et al J. Nat. Prod. 68, 189-93, (2005)

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Rab11 is required for epithelial cell viability, terminal differentiation, and suppression of tumor-like growth in the Drosophila egg chamber. Xu J PLoS ONE 6(5), e20180, (2011)

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Characterization of a tannase from Emericella nidulans immobilized on ionic and covalent supports for propyl gallate synthesis. Gonçalves HB, Jorge JA, Pessela BC, et al. Biotechnol. Lett. 35(4), 591-8, (2013)

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Localization of lipoxygenase activity on the oil bodies and in protoplasts using a novel fluorescence imaging method. Yadav MK and Bhatla SC Plant Physiol. Biochem. 49(2), 230-4, (2011)

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The antiangiogenic and antinociceptive activities of n-propyl gallate. Jung HJ and Lim CJ Phytother Res. 25(10), 1570-3, (2011)

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Imbalance of glomerular VEGF-NO axis in diabetic rats: prevention by chronic therapy with propyl gallate. Tian S, Gan Y, Li J, et al. J. Nephrol. 24(4), 499-506, (2011)

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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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Effect of antioxidants and silicates on peroxides in povidone. Narang AS, Rao VM, Desai DS. J. Pharm. Sci. 101, 127-139, (2012)

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Propyl gallate synthesis using acidophilic tannase and simultaneous production of tannase and gallic acid by marine Aspergillus awamori BTMFW032. Beena PS, Basheer SM, Bhat SG, et al. Appl. Biochem. Biotechnol. 164(5), 612-28, (2011)

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Effects of a dietary antioxidant blend and vitamin E on fatty acid profile, liver function, and inflammatory response in broiler chickens fed a diet high in oxidants. Lu T, Harper AF, Zhao J, et al. Poult. Sci. 93(7), 1658-66, (2014)

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Oxidative stress augments the secretion of atrial natriuretic peptide in isolated rat atria. Shah A, Gao S, Oh YB, et al. Peptides 32(6), 1172-8, (2011)

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In vivo effects of propyl gallate, a novel Ca(2+) sensitizer, in a mouse model of dilated cardiomyopathy caused by cardiac troponin T mutation. Du CK, Zhan DY, and Morimoto S Life Sci. 109(1), 15-9, (2014)

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Utility of 4-chloro-7-nitrobenzofurazan for the spectrofluorimetric determination of butylated hydroxyanisole and propyl gallate in foodstuffs. Chen M, Tai Z, Hu X, et al. J. Food Sci. 77(4), C401-7, (2012)

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Contact depigmentation induced by propyl gallate. Pandhi D, Vij A, and Singal A Clin. Exp. Dermatol. 36(4), 366-8, (2011)

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The enhancement of propyl gallate-induced apoptosis in HeLa cells by a proteasome inhibitor MG132. You BR, Park WH. Oncol. Rep. 25, 871-877, (2011)

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The relationship between CD86 and CD54 protein expression and cytotoxicity following stimulation with contact allergen in THP-1 cells. Nukada, Y., et al. J. Toxicol. Sci. 36 (3), 313-324, (2011)

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Characterization of bioimprinted tannase and its kinetic and thermodynamics properties in synthesis of propyl gallate by transesterification in anhydrous medium. Nie G, Zheng Z, Gong G, et al. Appl. Biochem. Biotechnol. 167(8), 2305-17, (2012)

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Final report on the amended safety assessment of Propyl Gallate. Int. J. Toxicol. 26 Suppl 3, 89-118, (2007)

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Propyl gallate plays a nephroprotective role in early stage of diabetic nephropathy associated with suppression of glomerular endothelial cell proliferation and angiogenesis. Tian S, Tang J, Liu H, et al. Exp. Diabetes Res. 2012, 209567, (2012)

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Visible-light-promoted degradation of the antioxidants propyl gallate and t-butylhydroquinone: mechanistic aspects. Criado S, Allevi C, and García NA Redox Rep. 17(3), 131-8, (2012)

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Effects of dietary fat, butylated hydroxytoluene and propyl gallate on microsomal drug metabolism in rats. Nutr. Rev. 40(6), 189-91, (1982)

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Merck 14,7859

Beil. 10,IV,2003

Aldrich MSDS 1, 1552:C / Arctander, 2710 / Corp MSDS 1 (2), 2967:D / FT-IR 1 (2), 301:A / FT-IR 2 (2), 2854:D / FT-NMR 1 (2), 1261:B / Fenaroli / IR-Spectra (3), 1032:D / IR-Spectra (2), 903:G / NMR-Reference 2 (2), 295:A / RegBook 1 (2), 1909:K / Sax 6, 2310 / Sigma FT-IR 1 (2), 862:C / Structure Index 1, 306:D:5 / Vapor Phase 3, 1370:B

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