Glutaraldehyde

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Glutaraldehyde
Skeletal formula
Ball-and-stick model
Identifiers
CAS number 111-30-8 YesY
PubChem 3485
ChemSpider 3365 YesY
UNII T3C89M417N YesY
DrugBank DB03266
KEGG D01120 YesY
Jmol-3D images Image 1
Properties
Molecular formula C5H8O2
Molar mass 100.12 g mol−1
Appearance Clear liquid
Density 1.06 g/mL
Melting point −14 °C (7 °F; 259 K)
Boiling point 187 °C (369 °F; 460 K)
Solubility in water Miscible, reacts
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

Glutaraldehyde is an organic compound with the formula CH2(CH2CHO)2. A pungent colorless oily liquid, glutaraldehyde is used to disinfect medical and dental equipment. It is also used for industrial water treatment and as a preservative. It is mainly available as an aqueous solution, and in these solutions the aldehyde groups are hydrated.[1]

Production and structure[edit]

Glutaraldehyde is produced industrially by the oxidation of cyclopentene and by the Diels-Alder reaction of acrolein and methyl vinyl ether followed by hydrolysis.[1]

Like other dialdehydes (e.g., glyoxal), it does not exist as the dialdehyde but as the hydrate. These hydrates adopt several structures.[2]

GlutaldehydeHydrateEquilibria.png

Monomeric glutaraldehyde can polymerize by aldol condensation reaction yielding alpha, beta-unsaturated poly-glutaraldehyde. This reaction usually occurs at alkaline pH values.

Uses[edit]

Fixative[edit]

A glutaraldehyde solution of 0.1% to 1.0% concentration may be used for system disinfection and as a preservative for long term storage. Glutaraldehyde is used in biological electron microscopy as a fixative. It kills cells quickly by crosslinking their proteins and is usually employed alone or mixed with formaldehyde[3] 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 example of an application for treatment of proteins with glutaraldehyde is the inactivation of bacterial toxins to create toxoid vaccines, e.g., the pertussis (whooping cough) toxoid component in the Boostrix Tdap vaccine produced by GlaxoSmithKline.[4]

In a related application, glutaraldehyde is sometimes employed in the tanning of leather.

Biochemical reagent[edit]

Glutaraldehyde is frequently used in biochemistry applications as an amine-reactive homobifunctional crosslinker. The oligomeric state of proteins can be examined through this application. Glutaraldehyde is also used in SDS-PAGE to fix proteins and peptides prior to staining. Typically, a gel is treated with a 5% solution for approximately half an hour, after which it must be thoroughly washed to remove the yellow stain brought about by reacting with free tris.

Wart treatment[edit]

A solution of 10% w/w glutaraldehyde is sold under the name "Diswart Solution" to remove common and plantar warts. Product claims include: "Inactivates viruses and bacteria. Dries the wart surface. Stains the area treated brown, but will not harm the surrounding skin."

Hydraulic Fracturing (Fracking) Fluid[edit]

Glutaraldehyde has been listed as a component of hydraulic fracturing "fracking" fluid. It is included in the additive called Alpha 1427, as a biocide, according to Material Safety Data Sheets released to the Morgantown Utility Board by Northeast Natural Energy.[5][6] Bacterial growth can impair the production of oil and gas wells, and can be introduced into the formation from various sources including the source water, proppant, and polymer used in the hydraulic fracturing process. Glutaraldehyde is pumped as a liquid additive with the fracturing fluid to reduce or eliminate this source of formation and fracture conductivity damage.

Planted Aquariums[edit]

Glutaraldehyde is the main ingredient in Seachem Flourish Excel, a source of carbon dioxide used by plants in freshwater aquariums.[7]

Safety[edit]

As a strong sterilant, glutaraldehyde is toxic and a strong irritant.[8] There is no evidence of carcinogenic activity.[9]

References[edit]

  1. ^ a b Christian Kohlpaintner, Markus Schulte, Jürgen Falbe, Peter Lappe, Jürgen Weber (2005), "Aldehydes, Aliphatic", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a01_321.pub2 
  2. ^ Earl B. Whipple, Michael Ruta "Structure of Aqueous Glutaraldehyde" J. Org. Chem., 1974, vol. 39, 1666-1668. doi:10.1021/jo00925a015
  3. ^ Karnovsky, M.J. (1965). A formaldehyde-glutaraldehyde fixative of high osmolality for use in electron microscopy. Journal of Cell Biology 27: 137A–138A
  4. ^ Boostrix prescribing information, ©2009, GlaxoSmithKline
  5. ^ http://www.mub.org/pdfs/MIP/Fracking%20Fluid%20Info/Alpha_1427_MSDS.pdf.  Missing or empty |title= (help)[dead link]
  6. ^ http://www.mub.org/pdfs/MIP/Fracking%20Fluid%20Info/MUB_letter.pdf.  Missing or empty |title= (help)[dead link]
  7. ^ "Material Safety Data Sheet, Flourish Excel". Archived from the original on 13 May 2013. Retrieved 25 August 2014. 
  8. ^ Canadian Centre for Occupational Health and Safety (CCOHS) (a federal government site) > OSH Answers > Diseases, Disorders & Injuries > Asthma Document last updated on February 8, 2005
  9. ^ Toxicology and Carcinogenesis Studies of Glutaraldehyde

External links[edit]