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121-79-9

121-79-9 | Propyl 3,4,5-trihydroxybenzoate

CAS No: 121-79-9 Catalog No: AG003TZW MDL No:MFCD00002196

Product Description

Catalog Number:
AG003TZW
Chemical Name:
Propyl 3,4,5-trihydroxybenzoate
CAS Number:
121-79-9
Molecular Formula:
C10H12O5
Molecular Weight:
212.1993
MDL Number:
MFCD00002196
IUPAC Name:
propyl 3,4,5-trihydroxybenzoate
InChI:
InChI=1S/C10H12O5/c1-2-3-15-10(14)6-4-7(11)9(13)8(12)5-6/h4-5,11-13H,2-3H2,1H3
InChI Key:
ZTHYODDOHIVTJV-UHFFFAOYSA-N
SMILES:
CCCOC(=O)c1cc(O)c(c(c1)O)O
EC Number:
204-498-2
UNII:
8D4SNN7V92
NSC Number:
2626
FEMA Number:
2947

Properties

Complexity:
206  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
212.068g/mol
Formal Charge:
0
Heavy Atom Count:
15  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
212.201g/mol
Monoisotopic Mass:
212.068g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
87A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.8  

Literature

Title Journal
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Gallic acid, a metabolite of the antioxidant propyl gallate, inhibits gap junctional intercellular communication via phosphorylation of connexin 43 and extracellular-signal-regulated kinase1/2 in rat liver epithelial cells. Mutation research 20080201
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The efficacy of protective effects of tannic acid, gallic acid, ellagic acid, and propyl gallate against hydrogen peroxide-induced oxidative stress and DNA damages in IMR-90 cells. Molecular nutrition & food research 20070801
Allergic contact cheilitis from a lipstick misdiagnosed as herpes labialis: Subsequent worsening due to Zovirax contact allergy. The Australasian journal of dermatology 20070801
Anterograde tracing method using DiI to label vagal innervation of the embryonic and early postnatal mouse gastrointestinal tract. Journal of neuroscience methods 20070730
Ecotoxicological effects of the antioxidant additive propyl gallate in five aquatic systems. Water research 20070601
Investigating the location of propyl gallate at surfaces and its chemical microenvironment by (1)H NMR. Lipids 20070601
Capillary electrophoresis-amperometric determination of antioxidant propyl gallate and butylated hydroxyanisole in foods. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20070601
Evaluation of occasional nonresponse of a washed cod mince model to hemoglobin (Hb)-mediated oxidation. Journal of agricultural and food chemistry 20070530
Effect of molecular structure of phenolic families as hydroxycinnamic acids and catechins on their antioxidant effectiveness in minced fish muscle. Journal of agricultural and food chemistry 20070516
Comparative cytotoxicity of alkyl gallates on mouse tumor cell lines and isolated rat hepatocytes. Comparative biochemistry and physiology. Part A, Molecular & integrative physiology 20070401
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Estrogenic potency of food-packaging-associated plasticizers and antioxidants as detected in ERalpha and ERbeta reporter gene cell lines. Journal of agricultural and food chemistry 20060614
Inhibition of hemoglobin- and iron-promoted oxidation in fish microsomes by natural phenolics. Journal of agricultural and food chemistry 20060614
Electron spin resonance study of radicals generated in cellulose/N-methylmorpholine solutions after flash photolysis at 77 K. Magnetic resonance in chemistry : MRC 20060601
[Inhibitory action of propyl gallate on the activation of SAPK/JNK and p38MAPK induced by cerebral ischemia-reperfusion in rats]. Yao xue xue bao = Acta pharmaceutica Sinica 20060601
Glyoxal markedly compromises hepatocyte resistance to hydrogen peroxide. Biochemical pharmacology 20060528
[The effect of propyl gallate on the activity of various antifungal drugs against filamentous fungi in vitro]. [Zhonghua yan ke za zhi] Chinese journal of ophthalmology 20060401
Antioxidant and modified atmosphere packaging prevention of discoloration in pork bones during retail display. Meat science 20060401
In vivo fragmentation of the large subunit of ribulose-1,5-bisphosphate carboxylase by reactive oxygen species in an intact leaf of cucumber under chilling-light conditions. Plant & cell physiology 20060201
Propyl gallate-induced platelet aggregation in patients with end-stage renal disease: the influence of the haemodialysis procedure. Nephrology (Carlton, Vic.) 20060201
Physicochemical properties of natural phenolics from grapes and olive oil byproducts and their antioxidant activity in frozen horse mackerel fillets. Journal of agricultural and food chemistry 20060125
Comparative study of the alkyl and peroxy radical scavenging activities of polyphenols. Chemosphere 20060101
A dip in the chlorophyll fluorescence induction at 0.2-2 s in Trebouxia-possessing lichens reflects a fast reoxidation of photosystem I. A comparison with higher plants. Biochimica et biophysica acta 20060101
A multistate model for the fluorescence response of R-phycoerythrin. Photochemistry and photobiology 20060101
Purification, product characterization and kinetic properties of lipoxygenase from olive fruit (Olea europaea L.). Plant physiology and biochemistry : PPB 20060101
Radical scavenging and catalytic activity of metal-phenolic complexes. The journal of physical chemistry. B 20051222
Relationship of CD86 surface marker expression and cytotoxicity on dendritic cells exposed to chemical allergen. Toxicology and applied pharmacology 20051201
[Inhibiting effect of adenosine on platelet activation in vitro]. Zhongguo shi yan xue ye xue za zhi 20051201
[Application of cationic propyl gallate as inducer of thrombocyte aggregation for evaluating the platelet function of platelet donors]. Zhongguo shi yan xue ye xue za zhi 20051201
Optimization of the analysis of flavor volatile compounds by liquid-liquid microextraction (LLME). Application to the aroma analysis of melons, peaches, grapes, strawberries, and tomatoes. Journal of agricultural and food chemistry 20051116
Effects of propyl gallate on interaction between TNF-alpha and sTNFR-I using an affinity biosensor. Acta pharmacologica Sinica 20051001
Thiol reducing compounds prevent human amylin-evoked cytotoxicity. The FEBS journal 20051001
Kinetic study of the quenching reaction of singlet oxygen by tea catechins in ethanol solution. Free radical biology & medicine 20050915
Toxicogenomics concepts and applications to study hepatic effects of food additives and chemicals. Toxicology and applied pharmacology 20050901
Microencapsulated mycelium-bound tannase from Aspergillus niger: an efficient catalyst for esterification of propyl gallate in organic solvents. Applied biochemistry and biotechnology 20050901
Effects of electron transport inhibitors and uncouplers on the oxidation of ferrous iron and compounds interacting with ferric iron in Acidithiobacillus ferrooxidans. Canadian journal of microbiology 20050801
Anti-oxidants reduce the acute adverse effects of residual oil fly ash on the frog palate mucociliary epithelium. Environmental research 20050701
Modulatory effect of glutathione status and antioxidants on methylmercury-induced free radical formation in primary cultures of cerebral astrocytes. Brain research. Molecular brain research 20050613
Model system for testing the efficacy of antioxidants in muscle foods. Journal of agricultural and food chemistry 20050601
Determination and confirmation of five phenolic antioxidants in foods by LC/MS and GC/MS. Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan 20050601
Alpha-tocopherol oxidation in fish muscle during chilling and frozen storage. Journal of agricultural and food chemistry 20050518
Determination of antioxidants in cosmetics by micellar electrokinetic capillary chromatography with electrochemical detection. Journal of chromatography. A 20050513
Identification of a novel estrogen-sulfating cytosolic SULT from zebrafish: molecular cloning, expression, characterization, and ontogeny study. Biochemical and biophysical research communications 20050429
[Slide platelet aggregation test used as a monitor for patient treated with anti-pletelet drugs]. Zhongguo shi yan xue ye xue za zhi 20050401
Sequence-specific DNA damage by reactive oxygen species: Implications for carcinogenesis and aging. Environmental health and preventive medicine 20050301
Protective effect of active oxygen scavengers on protein degradation and photochemical function in photosystem I submembrane fractions during light stress. The FEBS journal 20050201
Effects of scavengers for active oxygen species on cell death by cryptogein. Phytochemistry 20050201
Bioactive constituents from Boswellia papyrifera. Journal of natural products 20050201
Protective effect of propyl gallate against myocardial oxidative stress-induced injury in rat. The Journal of pharmacy and pharmacology 20050101
Vitamin C-induced loss of redox-dependent viability in lung microvascular endothelial cells. Antioxidants & redox signaling 20050101
Preventing hepatocyte oxidative stress cytotoxicity with Mangifera indica L. extract (Vimang). Drug metabolism and drug interactions 20050101
In vitro effect of phenolic antioxidants on germination, growth and aflatoxin B accumulation by peanut Aspergillus section Flavi. Journal of applied microbiology 20050101
[Inhibition of peroxidase-catalyzed oxidation of chromogenic substrates by propyl gallate and its polydisulfide]. Prikladnaia biokhimiia i mikrobiologiia 20050101
Comparison of immunoreactivity to serotonin, FMRFamide and SCPb in the gut and visceral nervous system of larvae, pupae and adults of the yellow fever mosquito Aedes aegypti. Journal of insect science (Online) 20050101
Evaluation for safety of antioxidant chemopreventive agents. Antioxidants & redox signaling 20050101
Effects of tannic acid and its related compounds on food mutagens or hydrogen peroxide-induced DNA strands breaks in human lymphocytes. Mutation research 20041122
Radial expansion of root cells and elongation of root hairs of Arabidopsis thaliana induced by massive doses of gamma irradiation. Plant & cell physiology 20041101
[Comparison of platelet activators used in slide platelet aggregation test]. Zhongguo shi yan xue ye xue za zhi 20041001
Antioxidant capacity and lipophilic content of seaweeds collected from the Qingdao coastline. Journal of agricultural and food chemistry 20040811
Inhibition of Na-K-ATPase in thick ascending limbs by NO depends on O2- and is diminished by a high-salt diet. American journal of physiology. Renal physiology 20040801
[Study on interaction of Radix Paeoniae 801 and endothelin-1 by using a piezoelectric quartz crystal biosensor]. Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine 20040801
[Current status of research on Radix paeoniae 801]. Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine 20040801
[Use of assessment of aggregation of thrombocytes induced by cationic propyl gallate to estimate recurrence of cardiovascular complications]. Vnitrni lekarstvi 20040801
Direct involvement of hydrogen peroxide in curvature of wheat coleoptile in blue-light-treated and dark-grown coleoptiles. Biochemical and biophysical research communications 20040709
Phenolic acid derivatives with potential anticancer properties--a structure-activity relationship study. Part 1: methyl, propyl and octyl esters of caffeic and gallic acids. Bioorganic & medicinal chemistry 20040701
Redox state regulates HIF-1alpha and its DNA binding and phosphorylation in salmonid cells. Journal of cell science 20040701
Assessing aspirin responsiveness in subjects with multiple risk factors for vascular disease with a rapid platelet function analyzer. Blood coagulation & fibrinolysis : an international journal in haemostasis and thrombosis 20040601
A study of molecular complex formation between propyl gallate and ascorbic acid in the microemulsion phase of sodium dodecyl sulfate, pentanol and water system. Colloids and surfaces. B, Biointerfaces 20040601
Permeability characteristics and membrane affinity of flavonoids and alkyl gallates in Caco-2 cells and in phospholipid vesicles. Archives of biochemistry and biophysics 20040515
Modulation of beta-lactam resistance in Staphylococcus aureus by catechins and gallates. International journal of antimicrobial agents 20040501
[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations]. Ceska a Slovenska farmacie : casopis Ceske farmaceuticke spolecnosti a Slovenske farmaceuticke spolecnosti 20040501
Antioxidant evaluation in dessert spices compared with common food additives. Influence of irradiation procedure. Journal of agricultural and food chemistry 20040407
Effects of platelet inhibitors on propyl gallate-induced platelet aggregation, protein tyrosine phosphorylation, and platelet factor 3 activation. Blood coagulation & fibrinolysis : an international journal in haemostasis and thrombosis 20040401
Characterization of the acetaminophen-induced degradation of cytochrome P450-3A4 and the proteolytic pathway. Basic & clinical pharmacology & toxicology 20040401
Metal-mediated oxidative damage to cellular and isolated DNA by gallic acid, a metabolite of antioxidant propyl gallate. Mutation research 20040314
Antibacterial activity of akyl gallates against Bacillus subtilis. Journal of agricultural and food chemistry 20040310
Model lipophilic formulations of retinyl palmitate: influence of conservative agents on light-induced degradation. Journal of pharmaceutical and biomedical analysis 20040310
Evidence for mitochondrial-derived alternative oxidase in the apicomplexan parasite Cryptosporidium parvum: a potential anti-microbial agent target. International journal for parasitology 20040309
Antipsoriatic drug anthralin induces EGF receptor phosphorylation in keratinocytes: requirement for H(2)O(2) generation. Experimental dermatology 20040201
Alternative oxidase reduces the sensitivity of Mycosphaerella graminicola to QOI fungicides. Pest management science 20040101
Investigation of atmospheric oxidation of propyl gallate in an anionic surfactant system in the absence and presence of ascorbic acid. Journal of cosmetic science 20040101
The use of chlorhexidine/n-propyl gallate as a urine preservative. Clinical laboratory science : journal of the American Society for Medical Technology 20040101
The galloyl moiety of green tea catechins is the critical structural feature to inhibit fatty-acid synthase. Biochemical pharmacology 20031115
Changes in the activity of the alternative oxidase in Orobanche seeds during conditioning and their possible physiological function. Phytochemistry 20030901
In vitro characterization of a plastid terminal oxidase (PTOX). European journal of biochemistry 20030901
Advanced hemostatic dressing development program: animal model selection criteria and results of a study of nine hemostatic dressings in a model of severe large venous hemorrhage and hepatic injury in Swine. The Journal of trauma 20030901
Properties of restructured beef steaks from forage- and grain-fed cattle as affected by antioxidant and flavoring agents. Meat science 20030901
Endostatin induces autophagic cell death in EAhy926 human endothelial cells. Histology and histopathology 20030701
Chain-breaking antioxidant activity of natural polyphenols as determined during the chain oxidation of methyl linoleate in Triton X-100 micelles. Archives of biochemistry and biophysics 20030615
Analysis of docosahexaenoic acid biosynthesis in Crypthecodinium cohnii by 13C labelling and desaturase inhibitor experiments. Journal of biotechnology 20030612
Hydrogen peroxide scavenging, antioxidant and anti-radical activity of some phenolic acids. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20030601
cDNA cloning, expression, and functional characterization of a zebrafish SULT1 cytosolic sulfotransferase. Archives of biochemistry and biophysics 20030601
GVS-111 prevents oxidative damage and apoptosis in normal and Down's syndrome human cortical neurons. International journal of developmental neuroscience : the official journal of the International Society for Developmental Neuroscience 20030501
Antioxidant activity of 3-dehydroshikimic acid in liposomes, emulsions, and bulk oil. Journal of agricultural and food chemistry 20030423
Hyperoxia alters phorbol ester-induced phospholipase D activation in bovine lung microvascular endothelial cells. Antioxidants & redox signaling 20030401
Scavenging of reactive oxygen species by a novel glucurinated flavonoid antioxidant isolated and purified from spinach. Phytochemistry 20030301
Effect of a single dose aspirin on platelets in humans with multiple risk factors for coronary artery disease. European journal of pharmacology 20030221
Sequestering ability of butylated hydroxytoluene, propyl gallate, resveratrol, and vitamins C and E against ABTS, DPPH, and hydroxyl free radicals in chemical and biological systems. Journal of agricultural and food chemistry 20030212
Synthesis of antioxidant propyl gallate using tannase from Aspergillus niger van Teighem in nonaqueous media. Bioorganic & medicinal chemistry letters 20030210
Photodynamic effects of antioxidant substituted porphyrin photosensitizers on gram-positive and -negative bacterial. Photochemistry and photobiology 20030201
Methylmercury-induced reactive oxygen species formation in neonatal cerebral astrocytic cultures is attenuated by antioxidants. Brain research. Molecular brain research 20030131
Amyloid beta protein enhances the clearance of extracellular L-glutamate by cultured rat cortical astrocytes. Neuroscience research 20030101
Propyl gallate is a superoxide dismutase mimic and protects cultured lens epithelial cells from H2O2 insult. Experimental eye research 20030101
[Bimodal changes in the germination of seeds subjected to heat treatment]. Radiatsionnaia biologiia, radioecologiia 20030101
Purification and characterization of tannin acyl hydrolase from Aspergillus niger MTCC 2425. Journal of basic microbiology 20030101
Addition of a propyl gallate-based procoagulant to a fibrin bandage improves hemostatic performance in a swine arterial bleeding model. Thrombosis research 20021215
Anti-Salmonella activity of alkyl gallates. Journal of agricultural and food chemistry 20021106
Kinetic evaluation of the reactivity of flavonoids as radical scavengers. SAR and QSAR in environmental research 20021001
Oxidation, reduction, and methylation of carnosic acid by Nocardia. Journal of natural products 20020901
Involvement of a plastid terminal oxidase in plastoquinone oxidation as evidenced by expression of the Arabidopsis thaliana enzyme in tobacco. The Journal of biological chemistry 20020830
In vivo interactions between photosynthesis, mitorespiration, and chlororespiration in Chlamydomonas reinhardtii. Plant physiology 20020801
Allergic contact dermatitis from occupational propyl gallate exposure. Contact dermatitis 20020801
Molecular design of antifungal agents. Journal of agricultural and food chemistry 20020703
Generation of reactive oxygen species and activation of NF-kappaB by non-Abeta component of Alzheimer's disease amyloid. Journal of neurochemistry 20020701
Antioxidant functions of selected allium thiosulfinates and S-alk(en)yl-L-cysteine sulfoxides. Journal of agricultural and food chemistry 20020424
Promoting effects of combined antioxidant and sodium nitrite treatment on forestomach carcinogenesis in rats after initiation with N-methyl-N'-nitro-N-nitrosoguanidine. Cancer letters 20020408
[Simultaneous determination of five antioxidants in food by HPLC with fluorescence detection]. Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan 20020401
Thrombin-induced platelet microparticles improved the aggregability of cryopreserved platelets. Cryobiology 20020401
Ability of surfactant micelles to alter the partitioning of phenolic antioxidants in oil-in-water emulsions. Journal of agricultural and food chemistry 20020227
Bond dissociation enthalpies of polyphenols: the importance of cooperative effects. The Journal of organic chemistry 20020208
Anti-MRSA activity of alkyl gallates. Bioorganic & medicinal chemistry letters 20020121
The influence of model drugs on the preparation of pellets by extrusion/spheronization: II. Spheronization parameters. International journal of pharmaceutics 20020101
[The photodynamic inactivation of Candida guilliermondii in the presence of photodithazine]. Mikrobiologiia 20020101
[Polyphenolic antioxidants efficiently protect urease from inactivation by ultrasonic cavitation]. Prikladnaia biokhimiia i mikrobiologiia 20020101
Evaluation of the antioxidant properties of Mediterranean and tropical fruits compared with common food additives. Journal of food protection 20011201
Application of cationic propyl gallate as inducer of thrombocyte aggregation for evaluation of effectiveness of antiaggregation therapy. Biomedical papers of the Medical Faculty of the University Palacky, Olomouc, Czechoslovakia 20011201
Cytogenetic effects of propyl gallate in CHO-K1 cells. Mutation research 20011115
[Initial experience with use of cationic propyl gallate as an inducer of thrombocyte aggregation in evaluation of anti-aggregation therapy]. Vnitrni lekarstvi 20011101
In vitro activity of polyhydroxycarboxylates against herpesviruses and HIV. Antiviral chemistry & chemotherapy 20011101
Antioxidant compounds and Ca(2+) pathway blockers differentially protect against methylmercury and mercuric chloride neurotoxicity. Journal of neuroscience research 20011001
Antioxidant properties of Mediterranean spices compared with common food additives. Journal of food protection 20010901
Chlororespiration and the process of carotenoid biosynthesis. Biochimica et biophysica acta 20010817
Effects of phenolic propyl esters on the oxidative stability of refined sunflower oil. Journal of agricultural and food chemistry 20010801
H(2)O(2) mediates oxidative stress-induced epidermal growth factor receptor phosphorylation. Toxicology letters 20010706
Activity of key enzymes in microsomal and mitochondrial membranes depends on the redox reactions involving lipid radicals. Membrane & cell biology 20010701
Inhibitory effects of nitric oxide on oxidative phosphorylation in plant mitochondria. Nitric oxide : biology and chemistry 20010601
Monoparameter sensors for the determination of the antioxidants butylated hydroxyanisole and n-propyl gallate in foods and cosmetics by flow injection spectrophotometry. The Analyst 20010601
The role of 15-lipoxygenase in disruption of the peroxisomal membrane and in programmed degradation of peroxisomes in normal rat liver. The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society 20010501
The influence of type and quantity of model drug on the extrusion/spheronization of mixtures with microcrystalline cellulose. I. Extrusion parameters. International journal of pharmaceutics 20010417
In vitro activity of propyl gallate-azole drug combination against fluconazole- and itraconazole-resistant Candida albicans strains. Letters in applied microbiology 20010401
Activation of heat shock factor 1 by pyrrolidine dithiocarbamate is mediated by its activities as pro-oxidant and thiol modulator. Biochemical and biophysical research communications 20010223
Antifungal activity of octyl gallate: structural criteria and mode of action. Bioorganic & medicinal chemistry letters 20010212
Lysosomal membrane damage in soluble Abeta-mediated cell death in Alzheimer's disease. Neurobiology of disease 20010201
Polyhydroxybenzoates inhibit ascorbic acid activation of mitochondrial glycerol-3-phosphate dehydrogenase: implications for glucose metabolism and insulin secretion. The Journal of biological chemistry 20010126
Effect of dietary treatment with n-propyl gallate or vitamin E on the survival of mice exposed to phosgene. Journal of applied toxicology : JAT 20010101
Monoclonal antibody-directed analysis of benzo[a]pyrene metabolism in rat liver and extrahepatic tissues: effect of propyl and octyl gallate. Nutrition and cancer 20010101
Steroid hormone activity of flavonoids and related compounds. Breast cancer research and treatment 20000701
Antioxidant function of phenethyl-5-bromo-pyridyl thiourea compounds with potent anti-HIV activity. Bioorganic & medicinal chemistry letters 20000103
Interaction of 1-hydroxyethyl radical with antioxidant enzymes. Archives of biochemistry and biophysics 19991215
Chemoprevention of heterocyclic amine-induced carcinogenesis by phenolic compounds in rats. Cancer letters 19990901
Characterization of rabbit UDP-glucuronosyltransferase UGT1A7: tertiary amine glucuronidation is catalyzed by UGT1A7 and UGT1A4. Archives of biochemistry and biophysics 19970815
Butylated hydroxyanisole blocks the inhibitory effects of tumor necrosis factor-alpha on collagen production in human dermal fibroblasts. Journal of dermatological science 19960401
Inhibition of human immunodeficiency viral replication by tannins and related compounds. Antiviral research 19920501
Role of reactive oxygen in tumor promotion: implication of superoxide anion in promotion of neoplastic transformation in JB-6 cells by TPA. Carcinogenesis 19850201

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