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Chemistry

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Also known as: Peroxyacetic acid, Ethaneperoxoic acid, 79-21-0, Estosteril, Acetic peroxide, Peroxoacetic acid
Molecular Formula
C2H4O3
Molecular Weight
76.05  g/mol
InChI Key
KFSLWBXXFJQRDL-UHFFFAOYSA-N
FDA UNII
I6KPI2E1HD

Peroxyacetic Acid
A liquid that functions as a strong oxidizing agent. It has an acrid odor and is used as a disinfectant.
1 2D Structure

Peroxyacetic Acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
ethaneperoxoic acid
2.1.2 InChI
InChI=1S/C2H4O3/c1-2(3)5-4/h4H,1H3
2.1.3 InChI Key
KFSLWBXXFJQRDL-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(=O)OO
2.2 Other Identifiers
2.2.1 UNII
I6KPI2E1HD
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Acetyl Hydroperoxide

2. Acid, Peracetic

3. Acid, Peroxyacetic

4. Acid, Peroxyethanoic

5. Desoxone 1

6. Desoxone-1

7. Desoxone1

8. Dialax

9. Peracetate, Sodium

10. Peracetate, Zinc

11. Peracetic Acid, Sodium Salt

12. Peroxyacetic Acid

13. Peroxyethanoic Acid

14. Sodium Peracetate

15. Zinc Peracetate

2.3.2 Depositor-Supplied Synonyms

1. Peroxyacetic Acid

2. Ethaneperoxoic Acid

3. 79-21-0

4. Estosteril

5. Acetic Peroxide

6. Peroxoacetic Acid

7. Acetyl Hydroperoxide

8. Monoperacetic Acid

9. Osbon Ac

10. Proxitane 4002

11. Desoxon 1

12. Ethaneperoxic Acid

13. Hydroperoxide, Acetyl

14. Acide Peracetique

15. Acido Peroxiacetico

16. Peroxy Acetic Acid

17. I6kpi2e1hd

18. Chembl444965

19. Ncgc00166305-01

20. Caswell No. 644

21. Acecide

22. Proxitane

23. Acide Peracetique [french]

24. Acide Peroxyacetique

25. F50

26. Ccris 686

27. Acide Peroxyacetique [french]

28. Acido Peroxiacetico [spanish]

29. Kyselina Peroxyoctova [czech]

30. Kyselina Peroxyoctova

31. Lcap

32. Hsdb 1106

33. Einecs 201-186-8

34. Unii-i6kpi2e1hd

35. Epa Pesticide Chemical Code 063201

36. Brn 1098464

37. Aceticperoxide

38. Peractic Acid

39. Per-acetic Acid

40. Peroxacetic Acid

41. Acetic Acid Oxide

42. Peroxy-acetic Acid

43. Acooh

44. Acecide (tn)

45. Ch3co2oh

46. Ethaneperoxoic Acid, 9ci

47. Ch3c(o)ooh

48. Dsstox_cid_5853

49. Ec 201-186-8

50. Dsstox_rid_77948

51. Peracetic Acid [mi]

52. Dsstox_gsid_25853

53. 4-02-00-00390 (beilstein Handbook Reference)

54. Peracetic Acid [hsdb]

55. Peracetic Acid [mart.]

56. Dtxsid1025853

57. Peracetic Acid [who-dd]

58. Chebi:42530

59. Tox21_112402

60. Bdbm50266095

61. Mfcd00002128

62. Peroxyacetic Acid, >43% And With >6% Hydrogen Peroxide [forbidden]

63. Zinc38141555

64. Akos015837803

65. Db14556

66. Cas-79-21-0

67. Peracetic Acid 35-40% Wt In Acetic Acid

68. Peracetic Acid Solution, 8.7% In Acetic Acid

69. D03467

70. Q375140

71. Peracetic Acid Solution, 36-40 Wt. % In Acetic Acid

72. Peracetic Acid Solution 32 Wt. % In Dilute Acetic Acid

73. Peracetic Acid Solution, 32 Wt. % In Dilute Acetic Acid

74. Peroxyacetic Acid, >43% And With >6% Hydrogen Peroxide

75. Peracetic Acid Solution, Purum, ~39% In Acetic Acid (rt)

76. Peracetic Acid Solution, Purum, ~40% In Acetic Acid: Water

2.4 Create Date
2005-03-27
3 Chemical and Physical Properties
Molecular Weight 76.05 g/mol
Molecular Formula C2H4O3
XLogP3-0.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Exact Mass76.016043985 g/mol
Monoisotopic Mass76.016043985 g/mol
Topological Polar Surface Area46.5 Ų
Heavy Atom Count5
Formal Charge0
Complexity40.2
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 Drug Warning

Peracetic acid-ethanol sterilization (PES) with a preceding delipidation step is an effective sterilization method for allograft bone ... The aim of this study was to evaluate the effects of different incubation times of water, hydrogen peroxide and alcohol cleansing procedures combined with PES on biomechanical properties of freeze-dried cortical bone ... /The/ in vitro study indicates that the cleansing procedure proposed combined with PES affects the biomechanical properties of cortical bone only on a limited scale.

PMID:17892947 Haimi S et al; Biologicals 36 (2): 99-104 (2008)


Sterilization of allografts for anterior cruciate ligament (ACL) reconstruction has become an important prerequisite to prevent disease transmission. However, current sterilization techniques impair the biological or mechanical properties of such treated grafts. Peracetic acid (PAA) has been successfully used to sterilize bone allografts without these disadvantages and does not impair the mechanical properties of soft tissue grafts in vitro ... Whether PAA sterilization would influence recellularization, restoration of crimp length and pattern, and revascularization of ACL grafts during early healing /was examined using/an in vivo sheep model for open ACL reconstruction ... The histologic findings /were correlated/ with the restoration of anteroposterior stability and structural properties during load-to-failure testing. PAA slowed remodeling activity at 6 and 12 weeks compared to nonsterilized allografts and autografts. The mechanical properties of PAA grafts were also reduced compared to these control groups at both time points. /It was concluded that/ PAA sterilization currently should not be used to sterilize soft tissue grafts typically used in ACL reconstruction.

PMID:18491201 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2584264 Scheffler SU et al; Clin Orthopedics Related Res 466 (8): 1810-8 (2008)


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Oxidants

Electron-accepting molecules in chemical reactions in which electrons are transferred from one molecule to another (OXIDATION-REDUCTION). (See all compounds classified as Oxidants.)


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.)


5.2 Absorption, Distribution and Excretion

An in vitro dermal penetration assay at 37 C using 0.8 % PAA (non-corrosive) indicated a low dermal uptake of peracetic acid through the intact skin of pigs. When the skin of rats was exposed to a corrosive concentration of (14)C-labelled PAA, a considerable uptake of (14)C was found but it is unknown if the (14)C was present as peracetic acid, acetic acid, or CO2. It is expected that corrosive concentrations of PAA would compromise the normal barrier function of the skin.

Organization for Economic Cooperation and Development; SIDS Initial Assessment Profile (SIAP) for Peracetic acid (79-21-0), p.2 (SIAM 26, April 2008). Available from, as of October 5, 2010: https://webnet.oecd.org/Hpv/ui/SponsoredSubstances.aspx


Two reliable in vitro studies, using different analytical methods, showed a rapid degradation of peracetic acid in rat blood. When rat blood was diluted 1000 times, the half-life of peracetic acid was < 5 minutes. In undiluted blood the half-life is expected to be several seconds or less. For this reason the distribution of peracetic acid is probably very limited and it is not expected to be systemically available after exposure to peracetic acid solutions.

Organization for Economic Cooperation and Development; SIDS Initial Assessment Profile (SIAP) for Peracetic acid (79-21-0), p.2 (SIAM 26, April 2008). Available from, as of October 5, 2010: https://webnet.oecd.org/Hpv/ui/SponsoredSubstances.aspx


5.3 Metabolism/Metabolites

Degradation products have not been identified during kinetic studies. However, based on the structure of the substance the following degradation products are expected: acetic acid, oxygen, hydrogen peroxide and water. Hydrogen peroxide is also presumed to be rapidly degraded into oxygen and water.

Organization for Economic Cooperation and Development; SIDS Initial Assessment Profile (SIAP) for Peracetic acid (79-21-0), p.2 (SIAM 26, April 2008). Available from, as of October 5, 2010: https://webnet.oecd.org/Hpv/ui/SponsoredSubstances.aspx


5.4 Biological Half-Life

When rat blood was diluted 1000 times, the half-life of peracetic acid was < 5 min. In undiluted blood the half-life is expected to be several seconds or less.

Organization for Economic Cooperation and Development; SIDS Initial Assessment Profile (SIAP) for Peracetic acid (79-21-0), p.2 (SIAM 26, April 2008). Available from, as of October 5, 2010: https://webnet.oecd.org/Hpv/ui/SponsoredSubstances.aspx


5.5 Mechanism of Action

To explore possible mechanisms of the arachidonic acid deficiency of the RBC membrane in alcoholics, the effect of ethanol and its oxidized products, acetaldehyde and peracetic acid, with other peroxides on the accumulation of 14(C)arachidonate into RBC membrane lipids in vitro was compared. Incubation of erythrocytes with 50 mM ethanol or 3 mM acetaldehyde had no effect on arachidonate incorporation. Pretreatment of erythrocytes with 10 mM hydrogen peroxide, 0.1 mM cumene hydroperoxide or 0.1 mM t-butyl hydroperoxide had little effect on 14(C)arachidonate incorporation in the absence of azide. However, pretreatment of cells with N-ethylmaleimide, 0.1 mM peracetic acid or performic acid, with or without azide, inhibited arachidonate incorporation into phospholipids but not neutral lipids. In chase experiments, peracetate also inhibited transfer of arachidonate from neutral lipids to phospholipids. To investigate a possible site of this inhibition of arachidonate transfer into phospholipids by percarboxylic acids, a repair enzyme, arachidonoyl CoA: 1-palmitoyl-sn-glycero-3-phosphocholine acyl transferase was assayed. As in intact cells, phospholipid biosynthesis was inhibited more by N-ethylmalemide and peracetic acid than by hydrogen peroxide, cumene hydroperoxide, and t-butyl hydroperoxide. Peracetic acid was the only active inhibitor among ethanol and its oxidized products studied and may deserve further examination in ethanol toxicity.

PMID:1900205 Allen DW et al; Biochim Biophys Acta 1081 (3): 267-73 (1991)


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