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2D Structure
Also known as: Oxepan-2-one, Epsilon-caprolactone, 6-hexanolactone, 2-oxepanone, 502-44-3, Hexan-6-olide
Molecular Formula
C6H10O2
Molecular Weight
114.14  g/mol
InChI Key
PAPBSGBWRJIAAV-UHFFFAOYSA-N
FDA UNII
56RE988L1R

1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
oxepan-2-one
2.1.2 InChI
InChI=1S/C6H10O2/c7-6-4-2-1-3-5-8-6/h1-5H2
2.1.3 InChI Key
PAPBSGBWRJIAAV-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1CCC(=O)OCC1
2.2 Other Identifiers
2.2.1 UNII
56RE988L1R
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Epsilon-caprolactone

2. Epsilon-captolactamium Hydrogen Sulfate

2.3.2 Depositor-Supplied Synonyms

1. Oxepan-2-one

2. Epsilon-caprolactone

3. 6-hexanolactone

4. 2-oxepanone

5. 502-44-3

6. Hexan-6-olide

7. Hexano-6-lactone

8. 6-hexanolide

9. E-caprolactone

10. 1-oxa-2-oxocycloheptane

11. 1,6-hexanolide

12. Epsilon-caprolactone Monomer

13. Placcel M

14. Polycaprolactone

15. 6-hydroxyhexanoic Acid Lactone

16. 2-oxacycloheptanone

17. 24980-41-4

18. Hexanoic Acid, Epsilon-lactone

19. .epsilon.-caprolactone

20. Hexamethylene Oxide, 2-oxo-

21. 6-caprolactone Monomer

22. 2-oxohexamethylene Oxide

23. 6-hydroxyhexanoic Acid, Epsilon-lactone

24. Chembl373123

25. Chebi:17915

26. 56re988l1r

27. Hexanoic Acid, 6-hydroxy-, .epsilon.-lactone

28. Epsilon-kaprolakton

29. Epsilon-kaprolakton [czech]

30. Hsdb 5670

31. 2-oxepanone, Homopolymer

32. Einecs 207-938-1

33. Brn 0106919

34. Unii-56re988l1r

35. 6-hexanalactone

36. Hexanoic Acid, 6-hydroxy-, Epsilon-lactone

37. Epsilon-hexalactone

38. Epsilon Caprolactone

39. Ece

40. Epsilon -caprolactone

41. .epsilon.-kaprolakton

42. Tone Eceq

43. Dsstox_cid_7159

44. Bmse000493

45. Caprolactone [hsdb]

46. Ec 207-938-1

47. Epsilon-caprolactone, 97%

48. Dsstox_rid_78329

49. Dsstox_gsid_27159

50. Schembl10850

51. 5-17-09-00034 (beilstein Handbook Reference)

52. Caprolactone, Epsilon-

53. .epsilon.-caprolactone Monomer

54. .epsilon.-hexanolactone

55. Dtxsid4027159

56. Hexanoic Acid, .epsilon.-lactone

57. Zinc388417

58. Epsilon-caprolactone [inci]

59. Oxepan-2-one; Epsilon-caprolactone

60. Hexanoic Acid, 6-hydroxy-, Lactone

61. Tox21_200445

62. Bbl011394

63. Bdbm50167993

64. C0059

65. Mfcd00003267

66. Mfcd00084404

67. Stl146497

68. Akos005721108

69. Cs-w016607

70. Polycaprolactonemn 70,000-90,000

71. Ncgc00248619-01

72. Ncgc00257999-01

73. Polycaprolactone (med Mw ~ 50.000)

74. As-14738

75. Cas-502-44-3

76. Db-051739

77. Ft-0625678

78. C01880

79. D70255

80. A828019

81. Q288104

82. Sr-01000944724

83. Sr-01000944724-1

84. W-109083

85. F0001-1311

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 114.14 g/mol
Molecular Formula C6H10O2
XLogP30
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass114.068079557 g/mol
Monoisotopic Mass114.068079557 g/mol
Topological Polar Surface Area26.3 Ų
Heavy Atom Count8
Formal Charge0
Complexity88.5
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

The incorporation of estramustine into biodegradable waxy type copolyesters, prepared by direct copolycondensation of epsilon-caprolactone and delta-valerolactone in the absence of catalysts, to apply as implantable matrices for drug delivery systems, is described and the in vivo capability of the implantable device was evaluated by implanting into the back of male rats. The copolyesters are much more subject to erosion than their homopolyesters, in which the degradation is further accelerated by the action of lipase type enzyme. The drug release, although accompanying a burst phenomenon in the initial stage, was kept constant throughout an experimental period of 19 wk from the first to twentieth wk. In this case, the release pattern was parallel to the degradation pattern, in support of the release being the rate-limiting step in the degradation of the polymer. The results showed about 75% of the initial drug content was still present in the device even after 20 wk of implantation. This finding means that the biodegradable poly(epsilon-caprolactone-co-delta-valerolactone) wax is useful as an implantable matrix for a drug delivery system which controls the release over a relatively long period of time. The in vivo activity of the drug was demonstrated by observing atrophy of the seminal vesicles and ventral prostate in male rats 10 wk after implantation.

Imasaka K et al; Int J Pharm 68 (Feb 1) 87-95 (1991)


The release of levonorgestrel from a poly(epsilon-caprolactone) capsule implanted subdermally in 8 women was studied over 5 menstrual cycles. All subjects except one experienced suppression of ovulation while the capsule was in place (one cycle). The capsules contained 16 mg of drug and 61 mg of ethyl oleate as a suspending vehicle. There was a wide range of serum levels of the drug. Suppression of ovulation appeared to occur at a serum level of 300 pg/ml or greater.

PMID:6402933 Ory SJ et al; Am J Obstet Gynecol 145 (Mar 1): 600-5 (1983)


5 Pharmacology and Biochemistry
5.1 Mechanism of Action

CAPROLACTONE INHIBITED PROTEOLYTIC & FIBRINOLYTIC ACTIVITIES OF HUMAN PLASMIN. IN VERY LOW CONCN, IT ALSO INHIBITED ACTIVATION OF PLASMINOGEN THROUGH PLASMIN-STREPTOKINASE ACTIVATOR & HUMAN UROKINASE.

PMID:4225897 AUERSWALD W, DOLESCHEL W; SCIENCE 156 (3779): 1244 (1967)