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Wikipedia

Glutaraldehyde

February 24, 2023

Glutaraldehyde is an organic compound with the formula (CH2)3(CHO)2. The molecule consists of a five carbon chain doubly terminated with formyl (CHO) groups. It is usually used as a solution in water, and such solutions exists as a collection of hydrates, cyclic derivatives, and condensation products, several of which interconvert. Because the molecule has two carbonyl group is reactive to primary amine groups (even as its hydrates), it can function as a crosslinking agent for any substance with primary amine groups and develop imine connected links. Crosslinking rigidifies and deactivates many biological functions, so in this way, glutaraldehyde solutions are used as biocides and as fixative. It is sold under the brandname Cidex and Glutaral.[3][4][5][6] As a disinfectant, it is used to sterilize surgical instruments.[3]

Glutaraldehyde
Names
Preferred IUPAC name
Pentanedial[1]
Other names
Glutaraldehyde
Glutardialdehyde
Glutaric acid dialdehyde
Glutaric aldehyde
Glutaric dialdehyde
1,5-Pentanedial
Identifiers
  • 111-30-8 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 3365 Y
DrugBank
  • DB03266 Y
ECHA InfoCard 100.003.506
KEGG
  • D01120 Y
  • 3485
UNII
  • T3C89M417N Y
  • DTXSID6025355
  • InChI=1S/C5H8O2/c6-4-2-1-3-5-7/h4-5H,1-3H2 Y
    Key: SXRSQZLOMIGNAQ-UHFFFAOYSA-N Y
  • InChI=1/C5H8O2/c6-4-2-1-3-5-7/h4-5H,1-3H2
    Key: SXRSQZLOMIGNAQ-UHFFFAOYAO
  • O=CCCCC=O
Properties
C5H8O2
Molar mass 100.117
Appearance Clear liquid
Odor pungent[2]
Density 1.06 g/mL
Melting point −14 °C (7 °F; 259 K)
Boiling point 187 °C (369 °F; 460 K)
Miscible, reacts
Vapor pressure 17 mmHg (20°C)[2]
Hazards
GHS labelling:
Danger
H302, H314, H317, H331, H334, H400
P260, P264, P270, P271, P272, P273, P280, P284, P301+P312, P302+P352, P304+P340, P305+P351+P338, P311, P330, P332+P313, P403+P233, P405, P501
NFPA 704 (fire diamond)
2
2
0
Flash point noncombustible[2]
0.2 ppm (0.82 mg/m3) (TWA), 0.05 ppm (STEL)
Lethal dose or concentration (LD, LC):
134 mg/kg (rat, oral); 2,560 mg/kg (rabbit, dermal)
NIOSH (US health exposure limits):
REL (Recommended)
 0.2 ppm (0.8 mg/m3)[2]
Safety data sheet (SDS) CAS 111-30-8
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Uses

Biochemistry

Glutaraldehyde is used in biochemistry applications as an amine-reactive homobifunctional crosslinker and fixative.[7][8] It kills cells quickly by crosslinking their proteins. It is usually employed alone or mixed with formaldehyde[9] as the first of two fixative processes to stabilize specimens such as bacteria, plant material, and human cells. A second fixative procedure uses osmium tetroxide to crosslink and stabilize cell and organelle membrane lipids.

Another application for treatment of proteins with glutaraldehyde is the inactivation of bacterial toxins to generate toxoid vaccines, e.g., the pertussis (whooping cough) toxoid component in the Boostrix Tdap vaccine produced by GlaxoSmithKline.[10]

Material Science

In material science glutaraldehyde application areas range from polymers to metals and biomaterials. Glutaraldehyde is commonly used as fixing agent before characterization of biomaterials for microscopy. Glutaraldehyde is a powerful crosslinking agent for many polymers containing primer amine groups.[citation needed]. Glutaraldehdye also can be used for an interlinking agent to improve the adhesion force between two polymeric coatings.[11] Glutaraldehyde is also used to protect against corrosion of undersea pipes.[12]

Medical

Clinical uses

Glutaraldehyde is used as a disinfectant and medication.[3][4][13] Usually applied as a solution, it is used to sterilize surgical instruments and other areas.[3]

Dermatological uses

As a medication it is used to treat plantar warts.[4] For this purpose, a 10% w/v solution is used. It dries the skin, facilitating physical removal of the wart.[14]

Glutaraldehyde is also used in the treatment of hyperhidrosis under the control of dermatologists. In people who have frequent sweating but do not respond to aluminum chloride. Glutaraldehyde solution is an effective agent to treat palmar and plantar hyperhidrosis as an alternative to tannic acid and formaldehyde.[15]

Safety

Side effects include skin irritation.[4] If exposed to large amounts, nausea, headache, and shortness of breath may occur.[3] Protective equipment is recommended when used, especially in high concentrations.[3] Glutaraldehyde is effective against a range of microorganisms including spores.[3][16] Glutaraldehyde is a dialdehyde.[17] It works by a number of mechanisms.[16]

As a strong sterilant, glutaraldehyde is toxic and a strong irritant.[18] There is no strong evidence of carcinogenic activity,[19] However, some occupations that work with this chemical have an increased risk of some cancers.[19]

Production and reactions

Production

Glutaraldehyde is produced industrially by the catalytic oxidation of cyclopentene by hydrogen peroxide, which can be achieved in the presence of various tungstic acid-based[20] heteropoly acid catalysts.[21] This reaction essentially mimics ozonolysis. Alternatively it can be made by the Diels-Alder reaction of acrolein and vinyl ethers followed by hydrolysis.[22]

 

Reactions

Like other dialdehydes, (e.g., glyoxal) and simple aldehydes (e.g., formaldehyde), glutaraldehyde hydrates in aqueous solution, forming gem-diols. These diols in turn equilibrate with cyclic hemiacetal.[23][22][7] Monomeric glutaraldehyde polymerizes by aldol condensation and Michael reactions yielding alpha, beta-unsaturated poly-glutaraldehyde and related oligomers. This reaction occurs at alkaline pH values.[24]

 

A number of mechanisms have been invoked to explain the biocidal and fixative properties of glutaraldehyde.[16] Like many other aldehydes, it reacts with primary amines and thiol groups, which are common functional groups in proteins, nucleic acids and polymeric materials. Being bi-functional, glutaraldehyde is a crosslinker, which rigidifies macromolecular structures and shuts down their reactivity.[25]

 
Imine formation from a primary amines and the carbonyls of glutaraldehyde is the basis of its fixative and biocidal properties.

The aldehyde groups in glutaraldehyde are susceptible to formation of imines by reaction with the amines of lysine and nucleic acids. The derivatives from aldol condensation of pairs of glutaraldehyde also undergo imine formation.[24]

Use in the Aquarium Hobby

Glutaraldehyde diluted with water is often sold as alternative to carbon dioxide gas injection for aquarium plants. It is commonly also used by aquarists in low doses as an algaecide.[26]

References

  1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 907. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ a b c d "CDC - NIOSH Pocket Guide to Chemical Hazards -Glutaraldehyde". www.cdc.gov. from the original on 13 January 2017. Retrieved 11 January 2017.
  3. ^ a b c d e f g World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. pp. 323, 325. hdl:10665/44053. ISBN 9789241547659.
  4. ^ a b c d British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. p. 825. ISBN 9780857111562.
  5. ^ Bonewit-West, Kathy (2015). Clinical Procedures for Medical Assistants. Elsevier Health Sciences. p. 96. ISBN 9781455776610. from the original on 6 October 2022. Retrieved 9 September 2017.
  6. ^ Sullivan, John Burke; Krieger, Gary R. (2001). Clinical Environmental Health and Toxic Exposures. Lippincott Williams & Wilkins. p. 601. ISBN 9780683080278. from the original on 10 October 2022. Retrieved 19 September 2020.
  7. ^ a b Srinivasan, Mythily; Sedmak, Daniel; Jewell, Scott (2002). "Effect of Fixatives and Tissue Processing on the Content and Integrity of Nucleic Acids". The American Journal of Pathology. 161 (6): 1961–1971. doi:10.1016/S0002-9440(10)64472-0. PMC 1850907. PMID 12466110.
  8. ^ Vakili, Mohammadtaghi; Rafatullah, Mohd; Salamatinia, Babak; Abdullah, Ahmad Zuhairi; Ibrahim, Mahamad Hakimi; Tan, Kok Bing; Gholami, Zahra; Amouzgar, Parisa (2014). "Application of chitosan and its derivatives as adsorbents for dye removal from water and wastewater: A review". Carbohydrate Polymers. 113: 115–130. doi:10.1016/j.carbpol.2014.07.007. PMID 25256466.
  9. ^ Karnovsky, M.J. (1965). A formaldehyde-glutaraldehyde fixative of high osmolality for use in electron microscopy. Journal of Cell Biology 27: 137A–138A
  10. ^ Boostrix prescribing information 1 February 2011 at the Wayback Machine, ©2009, GlaxoSmithKline
  11. ^ Erisen, Deniz. E (23 September 2022), "A novel chitosan and polydopamine interlinked bioactive coating for metallic biomaterials", Journal of Materials Science: Materials in Medicine, Springer-Nature, 33 (10): 65, doi:10.1007/s10856-022-06688-x, ISSN 1573-4838, PMC 9499904, PMID 36138240
  12. ^ Falck, Christian; Kleppe, Terje; Maribu, Jarleiv (23 December 1993). "Commissioning of long subsea pipelines - environmental aspects" (PDF). Norway (published 31 December 1997). OSTI 593571. {{cite journal}}: Cite journal requires |journal= (help)
  13. ^ Bonewit-West, Kathy (2015). Clinical Procedures for Medical Assistants. Elsevier Health Sciences. p. 96. ISBN 9781455776610. from the original on 23 September 2017.
  14. ^ NHS Choices: Glutarol 5 February 2015 at the Wayback Machine
  15. ^ Juhlin, L; Hansson, H (1968), "Topical glutaraldehyde for plantar hyperhidrosis", Archives of Dermatology, American Medical Association, 97 (3): 327–330, doi:10.1001/archderm.1968.01610090099017, ISSN 0003-987X, PMID 5641337
  16. ^ a b c Fraise, Adam P.; Maillard, Jean-Yves; Sattar, Syed (2012). Russell, Hugo and Ayliffe's Principles and Practice of Disinfection, Preservation and Sterilization. John Wiley & Sons. p. Chapter 2. ISBN 9781118425862. from the original on 23 September 2017.
  17. ^ Pfafflin, James R.; Ziegler, Edward N. (2006). Encyclopedia of Environmental Science and Engineering: A-L. CRC Press. p. 235. ISBN 9780849398438. from the original on 10 October 2022. Retrieved 19 September 2020.
  18. ^ Canadian Centre for Occupational Health and Safety (CCOHS) (a federal government site) > OSH Answers > Diseases, Disorders & Injuries > Asthma 27 April 2009 at the Wayback Machine Document last updated on 8 February 2005
  19. ^ a b Toxicology and Carcinogenesis Studies of Glutaraldehyde 10 October 2012 at the Wayback Machine
  20. ^ Chandler, Malcolm (15 April 2001). "Hydrogen Peroxide-Tungstic Acid". Encyclopedia of Reagents for Organic Synthesis: rh046. doi:10.1002/047084289X.rh046. ISBN 0471936235.
  21. ^ Furukawa, Hiroshi; Nakamura, Teiji; Inagaki, Hiroyuki; Nishikawa, Eiichiro; Imai, Chihiro; Misono, Makoto (5 May 1988). "Oxidation of Cyclopentene with Hydrogen Peroxide Catalyzed by 12-Heteropoly Acids". Chemistry Letters. 17 (5): 877–880. doi:10.1246/cl.1988.877.
  22. ^ a b Christian Kohlpaintner; Markus Schulte; Jürgen Falbe; Peter Lappe; Jürgen Weber (2008). "Aldehydes, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_321.pub2.
  23. ^ Whipple Earl B.; Ruta Michael (1974). "Structure of Aqueous Glutaraldehyde". J. Org. Chem. 39 (12): 1666–1668. doi:10.1021/jo00925a015.
  24. ^ a b Migneault, Isabelle; Dartiguenave, Catherine; Bertrand, Michel J.; Waldron, Karen C. (2004). "Glutaraldehyde: Behavior in aqueous solution, reaction with proteins, and application to enzyme crosslinking". BioTechniques. 37 (5): 790–802. doi:10.2144/04375RV01. PMID 15560135.
  25. ^ H. Uhr; B. Mielke; O. Exner; K. R. Payne; E. Hill (2013). "Biocides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a16_563.pub2.
  26. ^ Antiquis, Avus (20 September 2017). "Glutaraldehyde Revisited". praquatics.com - Aquarium Forums By Hobbyists For Hobbyists. from the original on 14 February 2022. Retrieved 10 October 2022.

External links

  • "Glutaraldehyde". Drug Information Portal. U.S. National Library of Medicine.
  • Glutaraldehyde: Sources of emissions AU National Pollutant Inventory
  • Glutaraldehyde US National Institute for Occupational Safety and Health
  • Glutaraldehyde NIST Standard Reference Data

February 24, 2023
glutaraldehyde, organic, compound, with, formula, molecule, consists, five, carbon, chain, doubly, terminated, with, formyl, groups, usually, used, solution, water, such, solutions, exists, collection, hydrates, cyclic, derivatives, condensation, products, sev. Glutaraldehyde is an organic compound with the formula CH2 3 CHO 2 The molecule consists of a five carbon chain doubly terminated with formyl CHO groups It is usually used as a solution in water and such solutions exists as a collection of hydrates cyclic derivatives and condensation products several of which interconvert Because the molecule has two carbonyl group is reactive to primary amine groups even as its hydrates it can function as a crosslinking agent for any substance with primary amine groups and develop imine connected links Crosslinking rigidifies and deactivates many biological functions so in this way glutaraldehyde solutions are used as biocides and as fixative It is sold under the brandname Cidex and Glutaral 3 4 5 6 As a disinfectant it is used to sterilize surgical instruments 3 Glutaraldehyde NamesPreferred IUPAC name Pentanedial 1 Other names GlutaraldehydeGlutardialdehydeGlutaric acid dialdehydeGlutaric aldehydeGlutaric dialdehyde1 5 PentanedialIdentifiersCAS Number 111 30 8 Y3D model JSmol Interactive imageChemSpider 3365 YDrugBank DB03266 YECHA InfoCard 100 003 506KEGG D01120 YPubChem CID 3485UNII T3C89M417N YCompTox Dashboard EPA DTXSID6025355InChI InChI 1S C5H8O2 c6 4 2 1 3 5 7 h4 5H 1 3H2 YKey SXRSQZLOMIGNAQ UHFFFAOYSA N YInChI 1 C5H8O2 c6 4 2 1 3 5 7 h4 5H 1 3H2Key SXRSQZLOMIGNAQ UHFFFAOYAOSMILES O CCCCC OPropertiesChemical formula C 5H 8O 2Molar mass 100 117Appearance Clear liquidOdor pungent 2 Density 1 06 g mLMelting point 14 C 7 F 259 K Boiling point 187 C 369 F 460 K Solubility in water Miscible reactsVapor pressure 17 mmHg 20 C 2 HazardsGHS labelling PictogramsSignal word DangerHazard statements H302 H314 H317 H331 H334 H400Precautionary statements P260 P264 P270 P271 P272 P273 P280 P284 P301 P312 P302 P352 P304 P340 P305 P351 P338 P311 P330 P332 P313 P403 P233 P405 P501NFPA 704 fire diamond 220Flash point noncombustible 2 Threshold limit value TLV 0 2 ppm 0 82 mg m3 TWA 0 05 ppm STEL Lethal dose or concentration LD LC LD50 median dose 134 mg kg rat oral 2 560 mg kg rabbit dermal NIOSH US health exposure limits REL Recommended 0 2 ppm 0 8 mg m3 2 Safety data sheet SDS CAS 111 30 8Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Uses 1 1 Biochemistry 1 2 Material Science 1 3 Medical 1 3 1 Clinical uses 1 3 2 Dermatological uses 2 Safety 3 Production and reactions 3 1 Production 3 2 Reactions 4 Use in the Aquarium Hobby 5 References 6 External linksUses EditBiochemistry Edit Glutaraldehyde is used in biochemistry applications as an amine reactive homobifunctional crosslinker and fixative 7 8 It kills cells quickly by crosslinking their proteins It is usually employed alone or mixed with formaldehyde 9 as the first of two fixative processes to stabilize specimens such as bacteria plant material and human cells A second fixative procedure uses osmium tetroxide to crosslink and stabilize cell and organelle membrane lipids Another application for treatment of proteins with glutaraldehyde is the inactivation of bacterial toxins to generate toxoid vaccines e g the pertussis whooping cough toxoid component in the Boostrix Tdap vaccine produced by GlaxoSmithKline 10 Material Science Edit In material science glutaraldehyde application areas range from polymers to metals and biomaterials Glutaraldehyde is commonly used as fixing agent before characterization of biomaterials for microscopy Glutaraldehyde is a powerful crosslinking agent for many polymers containing primer amine groups citation needed Glutaraldehdye also can be used for an interlinking agent to improve the adhesion force between two polymeric coatings 11 Glutaraldehyde is also used to protect against corrosion of undersea pipes 12 Medical Edit Clinical uses Edit Glutaraldehyde is used as a disinfectant and medication 3 4 13 Usually applied as a solution it is used to sterilize surgical instruments and other areas 3 Dermatological uses Edit As a medication it is used to treat plantar warts 4 For this purpose a 10 w v solution is used It dries the skin facilitating physical removal of the wart 14 Glutaraldehyde is also used in the treatment of hyperhidrosis under the control of dermatologists In people who have frequent sweating but do not respond to aluminum chloride Glutaraldehyde solution is an effective agent to treat palmar and plantar hyperhidrosis as an alternative to tannic acid and formaldehyde 15 Safety EditSide effects include skin irritation 4 If exposed to large amounts nausea headache and shortness of breath may occur 3 Protective equipment is recommended when used especially in high concentrations 3 Glutaraldehyde is effective against a range of microorganisms including spores 3 16 Glutaraldehyde is a dialdehyde 17 It works by a number of mechanisms 16 As a strong sterilant glutaraldehyde is toxic and a strong irritant 18 There is no strong evidence of carcinogenic activity 19 However some occupations that work with this chemical have an increased risk of some cancers 19 Production and reactions EditProduction Edit Glutaraldehyde is produced industrially by the catalytic oxidation of cyclopentene by hydrogen peroxide which can be achieved in the presence of various tungstic acid based 20 heteropoly acid catalysts 21 This reaction essentially mimics ozonolysis Alternatively it can be made by the Diels Alder reaction of acrolein and vinyl ethers followed by hydrolysis 22 Reactions Edit Like other dialdehydes e g glyoxal and simple aldehydes e g formaldehyde glutaraldehyde hydrates in aqueous solution forming gem diols These diols in turn equilibrate with cyclic hemiacetal 23 22 7 Monomeric glutaraldehyde polymerizes by aldol condensation and Michael reactions yielding alpha beta unsaturated poly glutaraldehyde and related oligomers This reaction occurs at alkaline pH values 24 A number of mechanisms have been invoked to explain the biocidal and fixative properties of glutaraldehyde 16 Like many other aldehydes it reacts with primary amines and thiol groups which are common functional groups in proteins nucleic acids and polymeric materials Being bi functional glutaraldehyde is a crosslinker which rigidifies macromolecular structures and shuts down their reactivity 25 Imine formation from a primary amines and the carbonyls of glutaraldehyde is the basis of its fixative and biocidal properties The aldehyde groups in glutaraldehyde are susceptible to formation of imines by reaction with the amines of lysine and nucleic acids The derivatives from aldol condensation of pairs of glutaraldehyde also undergo imine formation 24 Use in the Aquarium Hobby EditGlutaraldehyde diluted with water is often sold as alternative to carbon dioxide gas injection for aquarium plants It is commonly also used by aquarists in low doses as an algaecide 26 References Edit Nomenclature of Organic Chemistry IUPAC Recommendations and Preferred Names 2013 Blue Book Cambridge The Royal Society of Chemistry 2014 p 907 doi 10 1039 9781849733069 FP001 ISBN 978 0 85404 182 4 a b c d CDC NIOSH Pocket Guide to Chemical Hazards Glutaraldehyde www cdc gov Archived from the original on 13 January 2017 Retrieved 11 January 2017 a b c d e f g World Health Organization 2009 Stuart MC Kouimtzi M Hill SR eds WHO Model Formulary 2008 World Health Organization pp 323 325 hdl 10665 44053 ISBN 9789241547659 a b c d British national formulary BNF 69 69 ed British Medical Association 2015 p 825 ISBN 9780857111562 Bonewit West Kathy 2015 Clinical Procedures for Medical Assistants Elsevier Health Sciences p 96 ISBN 9781455776610 Archived from the original on 6 October 2022 Retrieved 9 September 2017 Sullivan John Burke Krieger Gary R 2001 Clinical Environmental Health and Toxic Exposures Lippincott Williams amp Wilkins p 601 ISBN 9780683080278 Archived from the original on 10 October 2022 Retrieved 19 September 2020 a b Srinivasan Mythily Sedmak Daniel Jewell Scott 2002 Effect of Fixatives and Tissue Processing on the Content and Integrity of Nucleic Acids The American Journal of Pathology 161 6 1961 1971 doi 10 1016 S0002 9440 10 64472 0 PMC 1850907 PMID 12466110 Vakili Mohammadtaghi Rafatullah Mohd Salamatinia Babak Abdullah Ahmad Zuhairi Ibrahim Mahamad Hakimi Tan Kok Bing Gholami Zahra Amouzgar Parisa 2014 Application of chitosan and its derivatives as adsorbents for dye removal from water and wastewater A review Carbohydrate Polymers 113 115 130 doi 10 1016 j carbpol 2014 07 007 PMID 25256466 Karnovsky M J 1965 A formaldehyde glutaraldehyde fixative of high osmolality for use in electron microscopy Journal of Cell Biology 27 137A 138A Boostrix prescribing information Archived 1 February 2011 at the Wayback Machine c 2009 GlaxoSmithKline Erisen Deniz E 23 September 2022 A novel chitosan and polydopamine interlinked bioactive coating for metallic biomaterials Journal of Materials Science Materials in Medicine Springer Nature 33 10 65 doi 10 1007 s10856 022 06688 x ISSN 1573 4838 PMC 9499904 PMID 36138240 Falck Christian Kleppe Terje Maribu Jarleiv 23 December 1993 Commissioning of long subsea pipelines environmental aspects PDF Norway published 31 December 1997 OSTI 593571 a href Template Cite journal html title Template Cite journal cite journal a Cite journal requires journal help Bonewit West Kathy 2015 Clinical Procedures for Medical Assistants Elsevier Health Sciences p 96 ISBN 9781455776610 Archived from the original on 23 September 2017 NHS Choices Glutarol Archived 5 February 2015 at the Wayback Machine Juhlin L Hansson H 1968 Topical glutaraldehyde for plantar hyperhidrosis Archives of Dermatology American Medical Association 97 3 327 330 doi 10 1001 archderm 1968 01610090099017 ISSN 0003 987X PMID 5641337 a b c Fraise Adam P Maillard Jean Yves Sattar Syed 2012 Russell Hugo and Ayliffe s Principles and Practice of Disinfection Preservation and Sterilization John Wiley amp Sons p Chapter 2 ISBN 9781118425862 Archived from the original on 23 September 2017 Pfafflin James R Ziegler Edward N 2006 Encyclopedia of Environmental Science and Engineering A L CRC Press p 235 ISBN 9780849398438 Archived from the original on 10 October 2022 Retrieved 19 September 2020 Canadian Centre for Occupational Health and Safety CCOHS a federal government site gt OSH Answers gt Diseases Disorders amp Injuries gt Asthma Archived 27 April 2009 at the Wayback Machine Document last updated on 8 February 2005 a b Toxicology and Carcinogenesis Studies of Glutaraldehyde Archived 10 October 2012 at the Wayback Machine Chandler Malcolm 15 April 2001 Hydrogen Peroxide Tungstic Acid Encyclopedia of Reagents for Organic Synthesis rh046 doi 10 1002 047084289X rh046 ISBN 0471936235 Furukawa Hiroshi Nakamura Teiji Inagaki Hiroyuki Nishikawa Eiichiro Imai Chihiro Misono Makoto 5 May 1988 Oxidation of Cyclopentene with Hydrogen Peroxide Catalyzed by 12 Heteropoly Acids Chemistry Letters 17 5 877 880 doi 10 1246 cl 1988 877 a b Christian Kohlpaintner Markus Schulte Jurgen Falbe Peter Lappe Jurgen Weber 2008 Aldehydes Aliphatic Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a01 321 pub2 Whipple Earl B Ruta Michael 1974 Structure of Aqueous Glutaraldehyde J Org Chem 39 12 1666 1668 doi 10 1021 jo00925a015 a b Migneault Isabelle Dartiguenave Catherine Bertrand Michel J Waldron Karen C 2004 Glutaraldehyde Behavior in aqueous solution reaction with proteins and application to enzyme crosslinking BioTechniques 37 5 790 802 doi 10 2144 04375RV01 PMID 15560135 H Uhr B Mielke O Exner K R Payne E Hill 2013 Biocides Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a16 563 pub2 Antiquis Avus 20 September 2017 Glutaraldehyde Revisited praquatics com Aquarium Forums By Hobbyists For Hobbyists Archived from the original on 14 February 2022 Retrieved 10 October 2022 External links Edit Glutaraldehyde Drug Information Portal U S National Library of Medicine Glutaraldehyde Sources of emissions AU National Pollutant Inventory Glutaraldehyde US National Institute for Occupational Safety and Health Glutaraldehyde NIST Standard Reference Data Portal Medicine Retrieved from https en wikipedia org w index php title Glutaraldehyde amp oldid 1138163296, wikipedia, wiki, book, books, library,

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