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375810 Sigma-Aldrich

Periodic acid

ACS reagent, 99%

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Properties

Related Categories ACS Grade Acids & Bases, Acids, Acids & Bases, Analytical Reagents, Analytical Reagents for General Use,
grade   ACS reagent
assay   99%
  99.0-101.0% (ACS specification)
impurities   ≤0.01% insolubles
  ≤0.01% other halogens
ign. residue   ≤0.01%
mp   122 °C(lit.)
anion traces   sulfate (SO42-): ≤0.01%
cation traces   Fe: ≤0.003%
  heavy metals: ≤0.005%

Description

Packaging

25, 100 g in glass bottle

Application

Periodic acid may be used in the following reactions:
• Oxidation of alcohols to ketones and aldehydes.1,2
• Oxidation hydroxylamine derivatives.3
• Oxidation of arenes to quinones.4
• Deprotection of the dithio- and oxathio-derivatives.5
• Oxidative degradation of epoxidized natural rubber (ENR).6
• Oxidation of urazoles and bis-urazoles to triazolinediones.7
• Oxidative cleavage of glucosazone.8

General description

Periodic acid is an inorganic acid commonly used as an oxidizing agent. Periodic acid oxidation9 is one of the steps in the periodate-resorcinol assay, used in the determination of sialic acid.10 Periodic acid reacts with 1,2 glycol linkage of carbohydrates to form aldehydes which can be stained by Schiff’s reagent. Therefore periodic-acid-Schiff′s reagent (PAS) is used in histochemistry to determine carbohydrates in tissue sections.11,12

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Periodic acid solution

1 g/dL in deionized water

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 3085 8(5.1) / PGII
WGK Germany 
3

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

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Peer-Reviewed Papers

References

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1. Pyridinium chlorochromate catalyzed oxidation of alcohols to aldehydes and ketones with periodic acid. Hunsen M. Tetrahedron Lett. 46(10), 1651-1653, (2005)

2. A mild and efficient oxidation of alcohols to aldehydes and ketones with periodic acid catalyzed by chromium (III) acetylacetonate. Xu L and Trudell ML. Tetrahedron Lett. 44(12), 2553-2555, (2003)

3. Further Observations Concerning the Periodic Acid Oxidation of Hydroxylamine Derivatives1. Emery TF and. Neilands JB. J. Org. Chem. 27(3), 1075-1077, (1962)

4. Chromium (VI) oxide-catalyzed oxidation of arenes with periodic acid. Yamazaki S. Tetrahedron Lett. 42(19), 3355-3357, (2001)

5. Deblocking of dithioacetals and oxathioacetals using periodic acid under mild nonaqueous conditions. Shi XX, et al. Tetrahedron Lett. 37(25), 4331-4334, (1996)

6. Chemical degradation of epoxidized natural rubber using periodic acid: Preparation of epoxidized liquid natural rubber. Phinyocheep P, et al. J. Appl. Polym. Sci. 95(1), 6-15, (2005)

7. The first report on the catalytic oxidation of urazoles to their corresponding triazolinediones via in situ catalytic generation of Br+ using periodic acid or oxone®/KBr system. Zolfigol MA, et al. J. Mol. Catal. A: Chem. 270(1), 219-224, (2007)

8. The Action of Periodic Acid on Glucose Phenylosazone. Chargaff E and Magasanik B. J. Am. Chem. Soc. 69(6), 1459-1461, (1947)

10. The sialic acids. XI. A periodate-resorcinol method for the quantitative estimation of free sialic acids and their glycosides. Jourdian GW, Dean L, and Roseman S J. Biol. Chem. 246(2), 430-5, (1971)

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11. Carbohydrate histochemistry studied by acetylation techniques: I. Periodic acid methods. McManus JFA and Cason JE. J. Exp. Med. 91(6), 651, (1950)

12. Histological and histochemical uses of periodic acid. McMANUS JF Stain Technol. 23(3), 99-108, (1948)

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Cross-comparison of protein recognition of sialic acid diversity on two novel sialoglycan microarrays. Padler-Karavani V, Song X, Yu H, et al. J. Biol. Chem. 287(27), 22593-608, (2012)

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Oxidized dextran as crosslinker for chitosan cryogel scaffolds and formation of polyelectrolyte complexes between chitosan and gelatin. Berillo D, Elowsson L, and Kirsebom H Macromol. Biosci. 12(8), 1090-9, (2012)

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An alternative role of C1q in bacterial infections: facilitating Streptococcus pneumoniae adherence and invasion of host cells. Agarwal V, Ahl J, Riesbeck K, et al. J. Immunol. 191(8), 4235-45, (2013)

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[Oxidation of carbohydrates by periodic acid]. Fujibayashi S Tanpakushitsu Kakusan Koso., Suppl:136-42, (1968)

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[Synthesis and identification of rutin complete antigen and analysis its immunogenicity]. Bao XY, He FY, Zeng JL, et al. Zhongguo Zhong Yao Za Zhi 38(3), 397-401, (2013)

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Sialic acid capture-and-release and LC-MS(n) analysis of glycopeptides. Nilsson J and Larson G Methods Mol. Biol. 951, 79-100, (2013)

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Enhancement of the nanofibrillation of wood cellulose through sequential periodate-chlorite oxidation. Liimatainen H, Visanko M, Sirviö JA, et al. Biomacromolecules 13(5), 1592-7, (2012)

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The GLIB technique for genome-wide mapping of 5-hydroxymethylcytosine. Pastor WA, Huang Y, Henderson HR, et al. Nat. Protoc. 7(10), 1909-17, (2012)

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Glycoproteomics enabled by tagging sialic acid- or galactose-terminated glycans. Ramya TN, Weerapana E, Cravatt BF, et al. Glycobiology 23(2), 211-21, (2013)

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Synthesis of 2-hydroxy-1,4-oxazin-3-ones through ring transformation of 3-hydroxy-4-(1,2-dihydroxyethyl)-β-lactams and a study of their reactivity. Mollet K, Goossens H, Piens N, et al. Chemistry 19(10), 3383-96, (2013)

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A nano-structured material for reliable speciation of chromium and manganese in drinking waters, surface waters and industrial wastewater effluents. Abdolmohammad-Zadeh H and Sadeghi GH Talanta 94, 201-8, (2012)

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Screening of polysaccharides for preparation of α-amylase conjugate to enhance stability and storage life. Jadhav SB and Singhal RS Carbohydr. Polym. 92(2), 1724-9, (2013)

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Beneficial effects of a novel RAGE inhibitor on early diabetic retinopathy and tactile allodynia. Guangyuan Li et al Mol. Vis. 17, 3156-65, (2011)

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A sensitive assay for palytoxins, ovatoxins and ostreocins using LC-MS/MS analysis of cleavage fragments from micro-scale oxidation. Selwood AI, van Ginkel R, Harwood DT, et al. Toxicon 60(5), 810-20, (2012)

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A periodate-cleavable linker for functional proteomics under slightly acidic conditions: application for the analysis of intracellular aspartic proteases. Maurer A, Zeyher C, Amin B, et al. J. Proteome Res. 12(1), 199-207, (2013)

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Periodate salts as pyrotechnic oxidizers: development of barium- and perchlorate-free incendiary formulations. Moretti JD, Sabatini JJ, and Chen G Angew. Chem. Int. Ed. Engl. 51(28), 6981-3, (2012)

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Pre-administration of L-tryptophan improved ADR-induced early renal failure in mice. Arioka Y, Yamamoto Y, Hoshi M, et al. Life Sci. 91(3-4), 100-6, (2012)

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Profiling glycol-split heparins by high-performance liquid chromatography/mass spectrometry analysis of their heparinase-generated oligosaccharides. Alekseeva A, Casu B, Torri G, et al. Anal. Biochem. 434(1), 112-22, (2013)

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Glucan of a somatic hybrid mushroom, pfls1h: structural characterization and study of immunological activities. Sen IK, Maji PK, Behera B, et al. Int. J. Biol. Macromol. 53, 127-32, (2013)

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Enabling Wittig reaction on site-specific protein modification. Han MJ, Xiong DC, and Ye XS Chem. Commun. (Camb.) 48(90), 11079-81, (2012)

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Structure analysis and antimutagenic activity of a novel salt-soluble polysaccharide from Auricularia polytricha. Zhou J, Chen Y, Xin M, et al. J. Sci. Food Agric. 93(13), 3225-30, (2013)

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Development of a hypersensitive periodate-cleavable amino acid that is methionine- and disulfide-compatible and its application in MHC exchange reagents for T cell characterisation. Amore A, Wals K, Koekoek E, et al. ChemBioChem. 14(1), 123-31, (2013)

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Controlled immobilisation of active enzymes on the cowpea mosaic virus capsid. Aljabali AA, Barclay JE, Steinmetz NF, et al. Nanoscale 4(18), 5640-5, (2012)

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Expulsion of Trichuris muris is associated with increased expression of angiogenin 4 in the gut and increased acidity of mucins within the goblet cell. D'Elia R BMC Genomics 10, 492, (2009)

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Chemical modification of carbohydrates in tissue sections may unmask mucin antigens. Kirkeby S Biotech. Histochem. 88(1), 19-26, (2013)

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Development of a compact chemiluminescence system coupled with capillary electrophoresis for carbohydrate analysis. Zhu J, Shu L, Wu M, et al. Talanta 93, 428-32, (2012)

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Deglycosylation effect of the mammalian sperm maturation antigen (SMA2) on serological reaction and acrosome reaction. Das T and Chatterjee T Anim. Reprod. Sci. 133(3-4), 176-83, (2012)

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Real-time monitoring of tyrosine hydroxylase activity using a plate reader assay. Vermeer LM, Higgins CA, Roman DL, et al. Anal. Biochem. 432(1), 11-5, (2013)

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Synthesis of a spacer-linked derivative of heptopyranosyl(α1-3)heptopyranose expressed in lipooligosaccharide and lipopolysaccharide. Yamasaki R, Nagahara K, Kishimoto K, et al. Biosci. Biotechnol. Biochem. 76(4), 772-7, (2012)

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Improved covalent immobilization of horseradish peroxidase on macroporous glycidyl methacrylate-based copolymers. Prodanović O, Prokopijević M, Spasojević D, et al. Appl. Biochem. Biotechnol. 168(5), 1288-301, (2012)

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9. Periodic Acid Oxidation. Jackson EL. Organic Reactions 2011th ed.,, 341-375

Merck 14,7171

Fieser 1,815 / Fieser 2,313 / Fieser 3,220 / Fieser 4,374 / Fieser 5,508 / Fieser 10,304 / Fieser 13,238

Corp MSDS 1 (2), 2731:D / RegBook 1 (3), 3253:H

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