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Chemistry

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Also known as: Pentanedial, Glutaral, 111-30-8, Glutaric dialdehyde, Cidex, 1,5-pentanedial
Molecular Formula
C5H8O2
Molecular Weight
100.12  g/mol
InChI Key
SXRSQZLOMIGNAQ-UHFFFAOYSA-N
FDA UNII
T3C89M417N

Glutaraldehyde
One of the protein CROSS-LINKING REAGENTS that is used as a disinfectant for sterilization of heat-sensitive equipment and as a laboratory reagent, especially as a fixative.
1 2D Structure

Glutaraldehyde

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
pentanedial
2.1.2 InChI
InChI=1S/C5H8O2/c6-4-2-1-3-5-7/h4-5H,1-3H2
2.1.3 InChI Key
SXRSQZLOMIGNAQ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C(CC=O)CC=O
2.2 Other Identifiers
2.2.1 UNII
T3C89M417N
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Cidex

2. Diswart

3. Gludesin

4. Glutaral

5. Glutardialdehyde

6. Glutarol

7. Korsolex

8. Novaruca

9. Sekumatic

10. Sonacide

11. Sporicidin

2.3.2 Depositor-Supplied Synonyms

1. Pentanedial

2. Glutaral

3. 111-30-8

4. Glutaric Dialdehyde

5. Cidex

6. 1,5-pentanedial

7. Sonacide

8. Glutardialdehyde

9. Pentane-1,5-dial

10. Glutaric Acid Dialdehyde

11. Glutaric Aldehyde

12. Glutaraldehyd

13. Glutaralum

14. Glutarol

15. Ucarcide

16. Aldesan

17. Alhydex

18. Hospex

19. 1,3-diformylpropane

20. Gluteraldehyde

21. 1,5-pentanedione

22. Aldesen

23. Novaruca

24. Sporicidin

25. Sterihyde L

26. Aldehyd Glutarowy

27. Nci-c55425

28. Glutaclean

29. Sterihyde

30. Aqucar

31. Veruca-sep

32. Relugan Gt

33. Relugan Gtw

34. Component Of Cidex

35. Glutarex 28

36. Nsc 13392

37. Sonacide (tn)

38. Cidex 7

39. Ucarcide 250

40. Relugan Gt 50

41. Sterihyde L (tn)

42. Coldcide-25 Microbiocide

43. Nsc-13392

44. Glutaral (jan/usp/inn)

45. Potentiated Acid Glutaraldehyde

46. Chebi:64276

47. T3c89m417n

48. 1, 5-pentanedial

49. Mfcd00007025

50. Ncgc00091110-01

51. Dsstox_cid_5355

52. Dsstox_rid_77761

53. Dsstox_gsid_25355

54. Glutaraldehyde Solution, 25%

55. Caswell No. 468

56. Glutaraldehyd [czech]

57. Glutaraldehyde Solution

58. 1,3-diformyl Propane

59. Diswart

60. Gludesin

61. Glutaralum [inn-latin]

62. Glutarol-1,5-pentanedial

63. Polyglutaraldehyde

64. Aldehyd Glutarowy [polish]

65. Glutaral [usan:inn:jan]

66. Cas-111-30-8

67. Poly(glutaraldehyde)

68. Ccris 3800

69. Hsdb 949

70. Einecs 203-856-5

71. Epa Pesticide Chemical Code 043901

72. Glutaric Dialdehyde Solution

73. Brn 0605390

74. Pentandial

75. Dioxopentane

76. Glutural

77. Ucarset

78. Verucasep

79. Glutaraldehyde Solution, For Electron Microscopy, ~25% In H2o

80. Virsal

81. Unii-t3c89m417n

82. Glutaral(usan)

83. Glutaric Dihydride

84. Glutaral [usan:usp:inn:jan]

85. Glutaraldehyde, 25% Soln

86. Glutaral Concentrate

87. Bactron K31

88. Ucarcide 225

89. Glutaraldehyde Solution (50% Or Less)

90. Pentanedial, Homopolymer

91. Glutaral [hsdb]

92. Glutaral [inci]

93. Glutaral [usan]

94. Pentane-1,5-dialdehyde

95. Glutaral [inn]

96. Glutaral [jan]

97. Glutaral, Inn, Usan

98. Glutaral [mart.]

99. Protectol Gda, Gt 50

100. Schembl836

101. Wln: Vh3vh

102. Glutaral [who-dd]

103. Ec 203-856-5

104. Glutaraldehyde [mi]

105. Pentane-1,5-dial Solution

106. Glutaraldehyde [fcc]

107. 4-01-00-03659 (beilstein Handbook Reference)

108. Bidd:er0299

109. Glutaraldehyde [vandf]

110. Glutaraldehyde Solution, 50%

111. Glutaral [usp Impurity]

112. Chembl1235482

113. Dtxsid6025355

114. Amy3308

115. Bio1_000462

116. Bio1_000951

117. Bio1_001440

118. Glutaraldehyde Solution, 25% W/w

119. Glutaraldehyde Solution, 50% W/w

120. Glutaraldehyde Solution, 70% W/w

121. Nsc13392

122. Str01121

123. Zinc1729593

124. Tox21_111083

125. Tox21_201742

126. Tox21_303295

127. Stl281872

128. Akos008967285

129. Glutaraldehyde (50per Cent In Water)

130. Db03266

131. Glutaric Dialdehyde, 25%sol. In Water

132. Glutaric Dialdehyde, 25% Sol. In Water

133. Ncgc00091110-02

134. Ncgc00091110-03

135. Ncgc00257231-01

136. Ncgc00259291-01

137. Glutaral Concentrate [usp Monograph]

138. Glutaraldehyde Solution, 25 Wt. % In H2o

139. Glutaraldehyde Solution, 50 Wt. % In H2o

140. Ft-0626730

141. G0067

142. G0068

143. En300-18037

144. D01120

145. Glutaraldehyde Solution, For Synthesis, 25.0%

146. Glutaraldehyde Solution, Grade Ii, 25% In H2o

147. A802339

148. Q416475

149. Glutaraldehyde Solution, For In Vitro Diagnostic Use

150. Q-201162

151. Glutaric Dialdehyde Solution, 50 Wt. % In H2o, Fcc

152. F2191-0161

153. Glutaraldehyde Solution, Saj First Grade, 20.0-26.0%

154. Glutaraldehyde Solution, Technical, ~25% In H2o (2.6 M)

155. Glutaraldehyde Solution, Technical, ~50% In H2o (5.6 M)

156. Glutaraldehyde Solution, 1.2 % (w/v) Glutaraldehyde In H2o

157. Glutaraldehyde Solution, For Electron Microscopy, ~50% In H2o

158. Glutaraldehyde Solution, For Electron Microscopy, ~8% In H2o

159. Glutaraldehyde Solution, 50% In H2o, Suitable For Photographic Applications

160. Glutaraldehyde Solution, Grade I, 25% In H2o, Specially Purified For Use As An Electron Microscopy Fixative

161. Glutaraldehyde Solution, Grade I, 50% In H2o, Specially Purified For Use As An Electron Microscopy Fixative Or Other Sophisticated Use

162. Glutaraldehyde Solution, Grade I, 70% In H2o, Specially Purified For Use As An Electron Microscopy Fixative Or Other Sophisticated Use

163. Glutaraldehyde Solution, Grade I, 8% In H2o, Specially Purified For Use As An Electron Microscopy Fixative Or Other Sophisticated Use

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 100.12 g/mol
Molecular Formula C5H8O2
XLogP3-0.5
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count4
Exact Mass100.052429494 g/mol
Monoisotopic Mass100.052429494 g/mol
Topological Polar Surface Area34.1 Ų
Heavy Atom Count7
Formal Charge0
Complexity51.1
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Disinfectants; Fixatives

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


VET: Disinfectants for foot-and-mouth disease were sprayed on livestock barns and roads from early February to May 2011. Although 90% of the disinfectant was concentrated on the roads, 10% was sprayed on cattle sheds and other sites where foot-and-mouth disease occurred. Since the outbreak of foot-and-mouth disease in November 2010, there has been a steady increase in disinfectant use. Consequently, its adverse environmental effects have prompted government officials to take preventive measures. The major chemical components of the disinfectants are citric acid, potassium sulfate base complex, quaternary ammonium compound, malic acid, and glutaraldehyde, ranging in amounts from tons to hundreds of tons. The exact amount of each component of the disinfectants could not be identified because the types of components used in the different commercial formulations overlapped. In this review, we obtained information on disinfectants that are widely used nationwide, including the types of major chemical components and their respective toxicities (both human and ecological).

PMID:23999336 Kim HM et al; J Infect Public Health 6(5):331-8 (2013)


For the topical treatment of warts, especially plantar warts.

Datapharm Communications Ltd; Electronic Medicines Compendium (eMC), Summary of Product Characteristics (SPC) for Glutarol (Last updated September 2005). Available from, as of July 9, 2010: https://www.medicines.org.uk/EMC/medicine/482/SPC/Glutarol+10%25+w+v+Cutaneous+Solution/


4.2 Drug Warning

... A 43-year-old woman /developed/ an acute hemorrhagic colitis after colonoscopy with ambulatory anesthesia. The diagnosis is likely to have been glutaraldehyde induced colitis (used for disinfection of the endoscope). The patient recovered spontaneously completely.

PMID:15158241 Grenet M et al; Ann Fr Anesth Reanim 23 (5): 499-500 (2004).


Six eyes of 6 patients developed toxic anterior segment syndrome (TASS) after uneventful phacoemulsification cataract surgery with implantation of a 3-piece acrylic IOL performed by 2 ophthalmologists on the same day. Clinical findings included corneal edema, Descemet's membrane folds, anterior chamber reaction, fibrin formation, and irregular, dilated, and unreactive pupils. ... Glutaraldehyde 2% solution was used inadvertently by the operating room staff who cleaned and sterilized reusable ocular instruments before autoclaving. None of the affected corneas improved. Additional surgical procedures were required and included penetrating keratoplasty, trabeculectomy, and glaucoma tube implantation. CONCLUSIONS: Glutaraldehyde in concentrations generally used for cold sterilization is highly toxic to the corneal endothelium. The operating room staff involved in sterilizing instruments should be well educated about and careful to follow the protocols to properly clean and sterilize reusable ocular instruments.

PMID:17010870 Unal M et al; J Cataract Refract Surg 32 (10): 1696-701(2006).


The sequelae of the inadvertent introduction of glutaraldehyde into the peritoneal cavity /are documented/. ... The clinical course, progressive histological changes to the bowel at different periods over the course of 1 year, and what long-term morbidity remains /are described/. The chemical structure, effects, and pathogenesis of glutaraldehyde are described as well as suggestions for avoiding similar problems in the future.

PMID:16769324 Karpelowsky JS et al; J Pediatr Surg 41 (6): e23-5 (2006).


The medical records of patients with acute rectocolitis following endoscopy treated at Kaohsiung Veterans General Hospital since 2001 were reviewed. The indication of endoscopy was health check-up for all patients. Published English-language studies regarding acute rectocolitis following endoscopy were also reviewed. RESULTS: An outbreak of six patients occurred in April 2002 and one cirrhotic patient was admitted in July 2008. All patients developed a self-limited syndrome of abdominal pain and bloody diarrhea within 48 h of uncomplicated endoscopy. One severely ill patient required hospitalization to receive intravenous fluid and antibiotics. After the investigation in April 2002, glutaraldehyde-induced colitis was diagnosed due to a defect in the endoscope-cleansing procedure. There were no deficiencies in the cleansing procedure in July 2008. Considering the patient's concomitant disease, we postulated that ischemic colitis with cirrhosis-related intestinal inflammation and endotoxemia was the possible diagnosis in this sporadic case. CONCLUSIONS: Endoscopists should be aware of this iatrogenic complication in patients presenting with acute rectocolitis, especially in those who have undergone recent endoscopic examination. An outbreak of acute rectocolitis following endoscopy should be considered glutaraldehyde-induced and should lead to an investigation of cleansing and equipment-disinfection procedures. In the absence of strong evidence of an outbreak, an infectious disease, or contamination of glutaraldehyde, a sporadic case should be considered ischemic colitis especially in patients with relevant concomitant diseases or predisposing factors.

PMID:19636574 Hsu CW et al; Int J Colorectal Dis 24 (10): 1193-200 (2009)


For more Drug Warnings (Complete) data for Glutaraldehyde (9 total), please visit the HSDB record page.


4.3 Minimum/Potential Fatal Human Dose

3-4. 3= Moderately toxic, probable oral lethal dose (human) 0.5-5 g/kg, between 1 ounce & 1 pint for 70 kg person (150 lb). 4=Very toxic, probable oral lethal dose (human) 50-500 mg/kg, between 1 teaspoon and 1 ounce for 70 kg person (150 lb).

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-187


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Disinfectants

Substances used on inanimate objects that destroy harmful microorganisms or inhibit their activity. Disinfectants are classed as complete, destroying SPORES as well as vegetative forms of microorganisms, or incomplete, destroying only vegetative forms of the organisms. They are distinguished from ANTISEPTICS, which are local anti-infective agents used on humans and other animals. (From Hawley's Condensed Chemical Dictionary, 11th ed) (See all compounds classified as Disinfectants.)


Fixatives

Agents employed in the preparation of histologic or pathologic specimens for the purpose of maintaining the existing form and structure of all of the constituent elements. Great numbers of different agents are used; some are also decalcifying and hardening agents. They must quickly kill and coagulate living tissue. (See all compounds classified as Fixatives.)


Cross-Linking Reagents

Reagents with two reactive groups, usually at opposite ends of the molecule, that are capable of reacting with and thereby forming bridges between side chains of amino acids in proteins; the locations of naturally reactive areas within proteins can thereby be identified; may also be used for other macromolecules, like glycoproteins, nucleic acids, or other. (See all compounds classified as Cross-Linking Reagents.)


5.2 Absorption, Distribution and Excretion

Glutaraldehyde is readily absorbed by oral, iv, and inhalation routes. It is absorbed dermally to a lesser extent.

Dart, R.C. (ed). Medical Toxicology. Third Edition, Lippincott Williams & Wilkins. Philadelphia, PA. 2004., p. 1249


In rats, glutaraldehyde is eliminated in the urine and expired gases.

Dart, R.C. (ed). Medical Toxicology. Third Edition, Lippincott Williams & Wilkins. Philadelphia, PA. 2004., p. 1249


Dermal and intravenous studies in the rat with dilute aqueous glutaraldehyde solutions (0.075-7.5%) showed that, in dermal tests, approx 5% was absorbed in the rat, and 30-50% in the rabbit. In the intravenous injection tests, approx 12% was absorbed in the rat and approx 33% in the rabbit. There were no significant differences between males and females in the study. The dermal absorption rate constant was low (0.2-2 hr) in each species. The elimination times were long for both intravenous injection (t0.5 for the rat 10 hr, rabbit 15-30 hr) and dermal application (t0.5 for the rat 40-110 hr, rabbit 20-100 hr), possibly due to the binding of glutaraldehyde to protein and the slow excretion of metabolites. The principal metabolite in both species was CO2 with other metabolites not identified. /It was/ proposed that the metabolism probably involved initial oxidation to corresponding carboxylic acids by aldehyde dehydrogenase, and then further oxidation to CO2.

Organization for Economic Cooperation and Development; Screening Information Data Set for Glutaraldehyde, CAS 111-30-8 p.67 (October 1998). Available from, as of June 1, 2010: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html


In vitro studies using human skin tissue showed that glutaraldehyde did not penetrate the thick skin of the sole, but 3-14% penetrated the stratum corneum of the chest and abdomen and 3-4% penetrated the epidermis.

Organization for Economic Cooperation and Development; Screening Information Data Set for Glutaraldehyde, CAS 111-30-8 p.67 (October 1998). Available from, as of June 1, 2010: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html


Material balance and pharmacokinetic studies were conducted with rats & rabbits including iv or topical dosing with [14C]glutaraldehyde. Intravenous dosing resulted in radiochemical recovery from 86% to 101%. Principal route of recovery was as CO2 at 22% to 80% of the administered dose (7%-28% urinary, 0.2%-5% feces). Epicutaneous dosing resutled in radiochemical recovery primarily in the skin at the site of application (31%-61%) with no consistent accumulation in any other tissue. Rabbits absorbed 33% to 53% of the epicutaneously administered dose & rats absorbed 4.1% to 8.7%. Pharmacokinetic studies indicated percutaneous radiochemical absorption of 0.3% to 2.1% for rats & 2.5% to 15.6% for rabbits under conservative study conditions that are likely to overestimate potential human exposure conditions.

American Conference of Governmental Industrial Hygienists. Documentation of the TLVs and BEIs with Other World Wide Occupational Exposure Values. 7th Ed. CD-ROM Cincinnati, OH 45240-1634 2013., p. 4


5.3 Metabolism/Metabolites

Glutaraldehyde is either metabolized by aldehyde dehydrogenase to yield an acid or inactivated by a reaction with sulphydryl groups using glutathione.

Dart, R.C. (ed). Medical Toxicology. Third Edition, Lippincott Williams & Wilkins. Philadelphia, PA. 2004., p. 1249


... In the intravenous injection tests, approx 12% was absorbed in the rat and approx 33% in the rabbit ... The principal metabolite in both species was CO2 with other metabolites not identified. /It was/ proposed that the metabolism probably involved initial oxidation to corresponding carboxylic acids by aldehyde dehydrogenase, and then further oxidation to CO2.

Organization for Economic Cooperation and Development; Screening Information Data Set for Glutaraldehyde, CAS 111-30-8 p.67 (October 1998). Available from, as of June 1, 2010: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html


... The probable major metabolic pathway /is considered to be/ initial oxidation to the corresponding mono- or dicarboxylic acid by aldehyde dehydrogenase and then further oxidation of the acidic intermediate to carbon dioxide.

American Conference of Governmental Industrial Hygienists. Documentation of the TLVs and BEIs with Other World Wide Occupational Exposure Values. 7th Ed. CD-ROM Cincinnati, OH 45240-1634 2013., p. 5


5.4 Biological Half-Life

The elimination times were long for both intravenous injection (t0.5 for the rat 10 hr, rabbit 15-30 hr) and dermal application (t0.5 for the rat 40-110 hr, rabbit 20-100 hr), possibly due to the binding of glutaraldehyde to protein and the slow excretion of metabolites.

Organization for Economic Cooperation and Development; Screening Information Data Set for Glutaraldehyde, CAS 111-30-8 p.67 (October 1998). Available from, as of June 1, 2010: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html


API Reference Price

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04-Jan-2021
05-Aug-2024
KGS
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Average Price (USD/KGS)

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Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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