| 词条 | Glutaraldehyde |
| 释义 |
| Watchedfields = changed | verifiedrevid = 450655655 | ImageFile = glutaraldehyde structure.png | ImageSize = 200px | ImageAlt = Skeletal formula of glutaraldehyde | ImageFile1 = Glutaraldehyde 3D ball.png | ImageSize1 = 200px | ImageAlt1 = Ball-and-stick model of the glutaraldehyde molecule | PIN = Pentanedial[1] | OtherNames = Glutaraldehyde Glutardialdehyde Glutaric acid dialdehyde Glutaric aldehyde Glutaric dialdehyde 1,5-Pentanedial |Section1={{Chembox Identifiers | UNII_Ref = {{fdacite|correct|FDA}} | UNII = T3C89M417N | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D01120 | InChI = 1/C5H8O2/c6-4-2-1-3-5-7/h4-5H,1-3H2 | InChIKey = SXRSQZLOMIGNAQ-UHFFFAOYAO | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C5H8O2/c6-4-2-1-3-5-7/h4-5H,1-3H2 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = SXRSQZLOMIGNAQ-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 111-30-8 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 3365 | PubChem = 3485 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB03266 | SMILES = O=CCCCC=O |Section2={{Chembox Properties | C=5 | H=8 | O=2 | MolarMass = 100.117 | Appearance = Clear liquid | Odor = pungent[2] | Density = 1.06 g/mL | MeltingPtC = -14 | BoilingPtC = 187 | Solubility = Miscible, reacts | VaporPressure = 17 mmHg (20°C)[2] |Section3={{Chembox Hazards | MainHazards = | FlashPt = | FlashPt_notes = noncombustible[2] | AutoignitionPt = | PEL = none[2] | IDLH = N.D.[2] | REL = C 0.2 ppm (0.8 mg/m3)[2] }}Glutaraldehyde, sold under the brandname Cidex and Glutaral among others, is a disinfectant, medication, preservative, and fixative.[3][4][5][6] As a disinfectant it is used to sterilize surgical instruments and other areas of hospitals.[3] As a medication it is used to treat warts on the bottom of the feet.[4] As a preservative, it is used in some cosmetics.[7][8] Glutaraldehyde is applied as a liquid.[3] 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.[3] Glutaraldehyde is effective against a range of microorganisms including spores.[3][21] It works by a number of mechanisms.[9] Glutaraldehyde came into medical use in the 1960s.[10] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[11] The wholesale cost in the developing world is about US$1.50–7.40 per liter of 2% solution.[12] There are a number of other commercial uses such as leather tanning.[13] UsesDisinfectionGlutaraldehyde is used as a disinfectant and medication.[14][15][16] Usually applied as a solution, it is used to sterilize surgical instruments and other areas.[3] FixativeGlutaraldehyde is used in biochemistry applications as an amine-reactive homobifunctional crosslinker and fixative prior to SDS-PAGE, staining, or electron microscopy. It kills cells quickly by crosslinking their proteins. It is usually employed alone or mixed with formaldehyde[17] 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. Fixation is usually followed by dehydration of the tissue in ethanol or acetone, followed by embedding in an epoxy resin or acrylic resin. 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.[18] In a related application, glutaraldehyde is sometimes employed in the tanning of leather and in embalming. Wart treatmentAs a medication it is used to treat warts on the bottom of the feet.[4] For this purpose, a 10% w/w solution is used. It dries the skin, facilitating physical removal of the wart.[19] Trade names include Diswart Solution and Glutarol. SafetySide 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.[3] Glutaraldehyde is effective against a range of microorganisms including spores.[3][9] As a strong sterilant, glutaraldehyde is toxic and a strong irritant.[20] There is no strong evidence of carcinogenic activity.[21] Some occupations that work with this chemical have an increased risk of some cancers.[21] Mechanism of actionA number of mechanisms have been invoked to explain the biocidal properties of glutaraldehyde.[22] Like many other aldehydes, it reacts with amines and thiol groups, which are common functional groups in proteins. Being bi-function, it is also a potential crosslinker.[23] Production and reactionsGlutaraldehyde is produced industrially by the oxidation of cyclopentene. Alternatively it can be made by the Diels-Alder reaction of acrolein and vinyl ethers followed by hydrolysis.[24] Like many other dialdehydes, (e.g., glyoxal) and simple aldehydes (e.g., formaldehyde), glutaraldehyde converts in aqueous solution to various hydrates that in turn convert to other equilibrating species.{{clarification needed|date=January 2019}}[25][26] Monomeric glutaraldehyde polymerizes by aldol condensation reaction yielding alpha, beta-unsaturated poly-glutaraldehyde. This reaction usually occurs at alkaline pH values. History and cultureGlutaraldehyde came into medical use in the 1960s.[27] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[28] The wholesale cost in the developing world is about US$1.50–7.40 per liter of 2% solution.[29] There are a number of other commercial uses such as leather tanning.[30] A glutaraldehyde solution of 0.1% to 1.0% concentration may be used as a biocide for system disinfection and as a preservative for long-term storage. It is a sterilant, killing endospores in addition to many microorganisms and viruses.[31] As a biocide, glutaraldehyde is a component of hydraulic fracturing ("fracking") fluid. It is included in the additive called Alpha 1427.[32] Bacterial growth impairs extraction of oil and gas from these wells. Glutaraldehyde is pumped as a component of the fracturing fluid to inhibit microbial growth. References1. ^{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 907 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}} 2. ^1 2 3 4 5 {{cite web|title=CDC - NIOSH Pocket Guide to Chemical Hazards -Glutaraldehyde|url=https://www.cdc.gov/niosh/npg/npgd0301.html|website=www.cdc.gov|accessdate=11 January 2017|deadurl=no|archiveurl=https://web.archive.org/web/20170113090414/https://www.cdc.gov/niosh/npg/npgd0301.html|archivedate=13 January 2017|df=}} 3. ^1 2 3 4 5 6 7 8 9 {{cite book|title=WHO Model Formulary 2008|date=2009|publisher=World Health Organization|isbn=9789241547659|pages=323, 325|url=http://apps.who.int/medicinedocs/documents/s16879e/s16879e.pdf|accessdate=8 January 2017|deadurl=no|archiveurl=https://web.archive.org/web/20161213060118/http://apps.who.int/medicinedocs/documents/s16879e/s16879e.pdf|archivedate=13 December 2016|df=}} 4. ^1 2 3 4 {{cite book|title=British national formulary : BNF 69|date=2015|publisher=British Medical Association|isbn=9780857111562|page=825|edition=69}} 5. ^{{cite book|last1=Bonewit-West|first1=Kathy|title=Clinical Procedures for Medical Assistants|date=2015|publisher=Elsevier Health Sciences|isbn=9781455776610|page=96|url=https://books.google.com/books?id=pTwcBgAAQBAJ&pg=PA96|language=en}} 6. ^{{cite book |last1=Sullivan |first1=John Burke |last2=Krieger |first2=Gary R. |title=Clinical Environmental Health and Toxic Exposures |date=2001 |publisher=Lippincott Williams & Wilkins |isbn=9780683080278 |page=601 |url=https://books.google.ca/books?id=PyUSgdZUGr4C&pg=PA601 |language=en}} 7. ^{{Cite web|url=https://www.ewg.org/skindeep/ingredient/702607/GLUTARAL/|title=GLUTARAL {{!}}{{!}} Skin Deep® Cosmetics Database {{!}} EWG|website=www.ewg.org|access-date=2019-02-25}} 8. ^{{Cite web|url=http://www.inchem.org/documents/sids/sids/111308.pdf|title=GLUTARADEHYDE CAS N°: 111-30-8|last=OECD Screening Information Database|first=|date=2019|website=|archive-url=|archive-date=|dead-url=|access-date=}} 9. ^1 2 {{cite book|last1=Fraise|first1=Adam P.|last2=Maillard|first2=Jean-Yves|last3=Sattar|first3=Syed|title=Russell, Hugo and Ayliffe's Principles and Practice of Disinfection, Preservation and Sterilization|date=2012|publisher=John Wiley & Sons|isbn=9781118425862|page=Chapter 2|url=https://books.google.com/books?id=b6Pz6kMw3akC&pg=PT50|language=en|deadurl=no|archiveurl=https://web.archive.org/web/20170923210311/https://books.google.com/books?id=b6Pz6kMw3akC&pg=PT50|archivedate=2017-09-23|df=}} 10. ^{{cite book|last1=Booth|first1=Anne|title=Sterilization of Medical Devices|date=1998|publisher=CRC Press|isbn=9781574910872|page=8|url=https://books.google.com/books?id=a-HfyG5XuM8C&pg=PA8|language=en|deadurl=no|archiveurl=https://web.archive.org/web/20170923210311/https://books.google.com/books?id=a-HfyG5XuM8C&pg=PA8|archivedate=2017-09-23|df=}} 11. ^{{cite web|title=WHO Model List of Essential Medicines (19th List)|url=http://www.who.int/medicines/publications/essentialmedicines/EML_2015_FINAL_amended_NOV2015.pdf?ua=1|work=World Health Organization|accessdate=8 December 2016|date=April 2015|deadurl=no|archiveurl=https://web.archive.org/web/20161213052708/http://www.who.int/medicines/publications/essentialmedicines/EML_2015_FINAL_amended_NOV2015.pdf?ua=1|archivedate=13 December 2016|df=}} 12. ^{{cite web|title=Glutaraldehyde|url=http://mshpriceguide.org/en/single-drug-information/?DMFId=375&searchYear=2014|website=International Drug Price Indicator Guide|accessdate=8 December 2016}} 13. ^{{cite book|last1=Rietschel|first1=Robert L.|last2=Fowler|first2=Joseph F.|last3=Fisher|first3=Alexander A.|title=Fisher's Contact Dermatitis|date=2008|publisher=PMPH-USA|isbn=9781550093780|page=359|url=https://books.google.com/books?id=dQBAzfyCeQ8C&pg=PA359|language=en|deadurl=no|archiveurl=https://web.archive.org/web/20170923210311/https://books.google.com/books?id=dQBAzfyCeQ8C&pg=PA359|archivedate=2017-09-23|df=}} 14. ^{{cite book|title=WHO Model Formulary 2008|date=2009|publisher=World Health Organization|isbn=9789241547659|pages=323, 325|url=http://apps.who.int/medicinedocs/documents/s16879e/s16879e.pdf|accessdate=8 January 2017|deadurl=no|archiveurl=https://web.archive.org/web/20161213060118/http://apps.who.int/medicinedocs/documents/s16879e/s16879e.pdf|archivedate=13 December 2016|df=}} 15. ^{{cite book|title=British national formulary : BNF 69|date=2015|publisher=British Medical Association|isbn=9780857111562|page=825|edition=69}} 16. ^{{cite book|last1=Bonewit-West|first1=Kathy|title=Clinical Procedures for Medical Assistants|date=2015|publisher=Elsevier Health Sciences|isbn=9781455776610|page=96|url=https://books.google.com/books?id=pTwcBgAAQBAJ&pg=PA96|language=en|deadurl=no|archiveurl=https://web.archive.org/web/20170923210311/https://books.google.com/books?id=pTwcBgAAQBAJ&pg=PA96|archivedate=2017-09-23|df=}} 17. ^Karnovsky, M.J. (1965). A formaldehyde-glutaraldehyde fixative of high osmolality for use in electron microscopy. Journal of Cell Biology 27: 137A–138A 18. ^Boostrix prescribing information {{webarchive|url=https://web.archive.org/web/20110201130749/http://www.gsksource.com/gskprm/en/US/adirect/gskprm?cmd=ProductDetailPage&product_id=1244167203071&featureKey=600532 |date=2011-02-01 }}, ©2009, GlaxoSmithKline 19. ^NHS Choices: Glutarol {{webarchive|url=https://web.archive.org/web/20150205153347/http://www.nhs.uk/medicine-guides/pages/MedicineOverview.aspx?medicine=Glutarol |date=2015-02-05 }} 20. ^Canadian Centre for Occupational Health and Safety (CCOHS) (a federal government site) > OSH Answers > Diseases, Disorders & Injuries > Asthma {{webarchive|url=https://web.archive.org/web/20090427164024/http://www.ccohs.ca/oshanswers/diseases/asthma.html |date=2009-04-27 }} Document last updated on February 8, 2005 21. ^1 Toxicology and Carcinogenesis Studies of Glutaraldehyde {{webarchive|url=https://web.archive.org/web/20121010200602/http://ntp.niehs.nih.gov/ntp/htdocs/LT_rpts/tr490.pdf |date=2012-10-10 }} 22. ^{{cite book|last1=Fraise|first1=Adam P.|last2=Maillard|first2=Jean-Yves|last3=Sattar|first3=Syed|title=Russell, Hugo and Ayliffe's Principles and Practice of Disinfection, Preservation and Sterilization|date=2012|publisher=John Wiley & Sons|isbn=9781118425862|page=Chapter 2|url=https://books.google.com/books?id=b6Pz6kMw3akC&pg=PT50|language=en|deadurl=no|archiveurl=https://web.archive.org/web/20170923210311/https://books.google.com/books?id=b6Pz6kMw3akC&pg=PT50|archivedate=2017-09-23|df=}} 23. ^{{Ullmann | author = H. Uhr, B. Mielke, O. Exner, K. R. Payne, E. Hill | title = Biocides | year = 2013| doi = 10.1002/14356007.a16_563.pub2}} 24. ^{{Ullmann|authors=Christian Kohlpaintner, Markus Schulte, Jürgen Falbe, Peter Lappe, Jürgen Weber|title=Aldehydes, Aliphatic|year=2008|doi= 10.1002/14356007.a01_321.pub2}} 25. ^{{cite journal |author1=Whipple Earl B. |author2=Ruta Michael | year = 1974 | title = Structure of Aqueous Glutaraldehyde | url = | journal = J. Org. Chem. | volume = 39 | issue = | pages = 1666–1668 | doi = 10.1021/jo00925a015 }} 26. ^{{Ullmann|authors=Christian Kohlpaintner, Markus Schulte, Jürgen Falbe, Peter Lappe, Jürgen Weber|title=Aldehydes, Aliphatic|year=2008|doi= 10.1002/14356007.a01_321.pub2}} 27. ^{{cite book|last1=Booth|first1=Anne|title=Sterilization of Medical Devices|date=1998|publisher=CRC Press|isbn=9781574910872|page=8|url=https://books.google.com/books?id=a-HfyG5XuM8C&pg=PA8|language=en|deadurl=no|archiveurl=https://web.archive.org/web/20170923210311/https://books.google.com/books?id=a-HfyG5XuM8C&pg=PA8|archivedate=2017-09-23|df=}} 28. ^{{cite web|title=WHO Model List of Essential Medicines (19th List)|url=http://www.who.int/medicines/publications/essentialmedicines/EML_2015_FINAL_amended_NOV2015.pdf?ua=1|work=World Health Organization|accessdate=8 December 2016|date=April 2015|deadurl=no|archiveurl=https://web.archive.org/web/20161213052708/http://www.who.int/medicines/publications/essentialmedicines/EML_2015_FINAL_amended_NOV2015.pdf?ua=1|archivedate=13 December 2016|df=}} 29. ^{{cite web|title=Glutaraldehyde|url=http://mshpriceguide.org/en/single-drug-information/?DMFId=375&searchYear=2014|website=International Drug Price Indicator Guide|accessdate=8 December 2016}} 30. ^{{cite book|last1=Rietschel|first1=Robert L.|last2=Fowler|first2=Joseph F.|last3=Fisher|first3=Alexander A.|title=Fisher's Contact Dermatitis|date=2008|publisher=PMPH-USA|isbn=9781550093780|page=359|url=https://books.google.com/books?id=dQBAzfyCeQ8C&pg=PA359|language=en|deadurl=no|archiveurl=https://web.archive.org/web/20170923210311/https://books.google.com/books?id=dQBAzfyCeQ8C&pg=PA359|archivedate=2017-09-23|df=}} 31. ^HCC lecture notes, 15 {{webarchive|url=https://web.archive.org/web/20150502072120/http://www.hccfl.edu/yc/science/mcb-2000-lecture-notes-dr-ketcham-only!.aspx |date=2015-05-02 }}: Control of microorganisms {{webarchive|url=https://web.archive.org/web/20150924025247/http://www.hccfl.edu/media/574949/15-control%20of%20microorganisms.pdf |date=2015-09-24 }} 32. ^{{cite web|url=http://www.mub.org/fracking-fluid-information|author=Morgantown Utility Board|title=Fracking Fluid Additives - Fracking Fluid MSDS's|deadurl=no|archiveurl=https://web.archive.org/web/20150205142049/http://www.mub.org/fracking-fluid-information|archivedate=2015-02-05|df=}}. Links to documents, including Alpha 1427 Material Safety Data Sheet External links
5 : Aldehydes|Disinfectants|Anatomical preservation|World Health Organization essential medicines|RTT |
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