ε-​Caprolactone

For research use only. Not for therapeutic Use.

  • CAT Number: R063930
  • CAS Number: 502-44-3
  • Molecular Formula: C6H10O2
  • Molecular Weight: 114.144
  • Purity: ≥95%
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Hexano-6-lactone(CAS: 502-44-3) is a epsilon-lactone that is oxepane substituted by an oxo group at position 2.


Catalog Number R063930
CAS Number 502-44-3
Synonyms

2-Oxepanone; Hexanoic Acid, 6-hydroxy-lactone; 1,6-Hexanolide; 2-Oxooxopane; 6-Hexanolactone; 6-Hexanolide; 6-Hydroxyhexanoic Acid Lactone; C 0702; Caprolactone; Caprolactone A; Epsilon-caprolactone; Hexamethylene Oxide, 2-oxo-; Hexanoic Acid, 6-hydr

Molecular Formula C6H10O2
Purity ≥95%
Storage -20°C
IUPAC Name oxepan-2-one
InChI InChI=1S/C6H10O2/c7-6-4-2-1-3-5-8-6/h1-5H2
InChIKey PAPBSGBWRJIAAV-UHFFFAOYSA-N
SMILES C1CCC(=O)OCC1
Reference

[1]. Int J Pharm. 2004 Jun 18;278(1):1-23. doi: 10.1016/j.ijpharm.2004.01.044.<br />
Poly-epsilon-caprolactone microspheres and nanospheres: an overview.<br />
Sinha VR(1), Bansal K, Kaushik R, Kumria R, Trehan A.<br />
Author information: (1)University Institute of Pharmaceutical Sciences, Panjab University, Chandigarh 160014, India. [email protected]<br />
Poly-epsilon-caprolactone (PCL) is a biodegradable, biocompatible and semicrystalline polymer having a very low glass transition temperature. Due to its slow degradation, PCL is ideally suitable for long-term delivery extending over a period of more than one year. This has led to its application in the preparation of different delivery systems in the form of microspheres, nanospheres and implants. Various categories of drugs have been encapsulated in PCL for targeted drug delivery and for controlled drug release. Microspheres of PCL either alone or of PCL copolymers have been prepared to obtain the drug release characteristics. This article reviews the advancements made in PCL-based microspheres and nanospheres with special reference to the method of preparation of these and their suitability in developing effective delivery systems.<br />
DOI: 10.1016/j.ijpharm.2004.01.044 PMID: 15158945<br />
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[2]. Langenbecks Arch Surg. 2019 Dec;404(8):1009-1016. doi: 10.1007/s00423-019-01843-5. Epub 2019 Nov 27.<br />
Poly-&epsilon;-caprolactone scaffold for the reinforcement of stapled small intestinal anastomoses: a randomized experimental study.<br />
Larsen KD(1), Westerholt M(1), Madsen GI(2), Le DQS(3), Qvist N(4)(5), Elleb&aelig;k MB(1).<br />
Author information: (1)Research Unit for Surgery, Odense University Hospital, University of Southern Denmark, Odense, Denmark. (2)Research Unit for Pathology, Odense University Hospital, University of Southern Denmark, Odense, Denmark. (3)Department of Clinical Medicine, Aarhus University, Palle Juul-Jensens Boulevard 82, 8200, Aarhus, Denmark. (4)Research Unit for Surgery, Odense University Hospital, University of Southern Denmark, Odense, Denmark. [email protected]. (5)Danish Centre for Regenerative Medicine (CRM), Odense University Hospital, J.B. Winsl&oslash;wsvej 4, 5000, Odense, Denmark. [email protected].<br />
BACKGROUND: Anastomotic leakage is a severe complication in gastrointestinal surgery. Different methods have been evaluated for anastomotic reinforcement to prevent anastomotic leakage. The aim of this study was to investigate the effect of a poly-&epsilon;-caprolactone (PCL) scaffold incorporated in the staple-line, on the anastomotic strength and histological wound healing, of small intestinal anastomoses in piglets. METHOD: This randomized experimental trial included 17 piglets. In each piglet, three end-to-end anastomoses were performed in the small intestine with a circular stapler, i.e. one control and two interventional anastomoses. On postoperative day 5, the anastomoses were resected and subjected to tension stretch test and histological examination. RESULTS: No anastomotic leakage occurred. In the interventional anastomoses, the mean value for maximal tensile strength was 15.7 N, which was significantly higher than control anastomoses 12.7 N (p = 0.01). No statistically significant differences were found between the two groups in the histopathological parameters. CONCLUSION: To conclude, this study has shown that the incorporation of a PCL scaffold in the staple-line was feasible and significantly increased the maximal tensile strength of small intestine anastomoses in piglets on postoperative day 5. The difference in histological parameters was not significantly distinct.<br />
DOI: 10.1007/s00423-019-01843-5 PMID: 31776655<br />
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[3]. PLoS One. 2019 Apr 8;14(4):e0214956. doi: 10.1371/journal.pone.0214956. eCollection 2019.<br />
Low molecular weight &epsilon;-caprolactone-p-coumaric acid copolymers as potential biomaterials for skin regeneration applications.<br />
Contardi M(1)(2), Alfaro-Pulido A(1), Picone P(3), Guzman-Puyol S(1), Goldoni L(4), Ben&iacute;tez JJ(5), Heredia A(6)(7), Barthel MJ(8), Ceseracciu L(9), Cusimano G(3), Brancato OR(3), Di Carlo M(3), Athanassiou A(1), Heredia-Guerrero JA(1).<br />
Author information: (1)Smart Materials, Istituto Italiano di Tecnologia, Genova, Italy. (2)DIBRIS, University of Genoa, Genoa, Italy. (3)Istituto di Biomedicina ed Immunologia Molecolare &quot;A. Monroy&quot;, CNR, Palermo, Italy. (4)Analytical Chemistry Facility, Istituto Italiano di Tecnologia, Genova, Italy. (5)Instituto de Ciencia de Materiales de Sevilla, Centro mixto CSIC-Universidad de Sevilla, Isla de la Cartuja, Sevilla, Spain. (6)Instituto de Hortofruticultura Subtropical y Mediterr&aacute;nea (IHSM), La Mayora Universidad de M&aacute;laga-CSIC Algarrobo-Costa, M&aacute;laga, Spain. (7)Departamento de Biolog&iacute;a Molecular y Bioqu&iacute;mica, Universidad de M&aacute;laga, M&aacute;laga, Spain. (8)Nanomaterials for Biomedical Applications, Istituto Italiano di Tecnologia, Genova, Italy. (9)Materials Characterization Facility, Istituto Italiano di Tecnologia, Genova, Italy.<br />
&epsilon;-caprolactone-p-coumaric acid copolymers at different mole ratios (&epsilon;-caprolactone:p-coumaric acid 1:0, 10:1, 8:1, 6:1, 4:1, and 2:1) were synthesized by melt-polycondensation and using 4-dodecylbenzene sulfonic acid as catalyst. Chemical analysis by NMR and GPC showed that copolyesters were formed with decreasing molecular weight as p-coumaric acid content was increased. Physical characteristics, such as thermal and mechanical properties, as well as water uptake and water permeability, depended on the mole fraction of p-coumaric acid. The p-coumarate repetitive units increased the antioxidant capacity of the copolymers, showing antibacterial activity against the common pathogen Escherichia coli. In addition, all the synthesized copolyesters, except the one with the highest concentration of the phenolic acid, were cytocompatible and hemocompatible, thus becoming potentially useful for skin regeneration applications.<br />
DOI: 10.1371/journal.pone.0214956 PMCID: PMC6453441 PMID: 30958838<br />
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[4]. Mol Biotechnol. 2019 May;61(5):345-354. doi: 10.1007/s12033-019-00168-4.<br />
Electrospun Poly-&epsilon;-Caprolactone (PCL)/Dicalcium Phosphate Dihydrate (DCPD) Composite Scaffold for Tissue Engineering Application.<br />
Taghavi MA(1)(2), Rabiee SM(3)(4), Jahanshahi M(2)(5), Nasiri F(6).<br />
Author information: (1)Department of Materials Engineering, Babol Noshirvani University of Technology, Babol, Iran. (2)Nanotechnology Research Institute, Babol Noshirvani University of Technology, Babol, Iran. (3)Department of Materials Engineering, Babol Noshirvani University of Technology, Babol, Iran. [email protected]. (4)Nanotechnology Research Institute, Babol Noshirvani University of Technology, Babol, Iran. [email protected]. (5)Department of Chemical Engineering, Babol Noshirvani University of Technology, Babol, Iran. (6)Department of Textile Engineering, Isfahan University of Technology, Isfahan, Iran.<br />
Recently electrospun scaffolds show excellent response in cell adhesion, growth, and tissue healing in comparison with other techniques. So in this study, PCL and PCL/DCPD scaffolds were designed and prepared with electrospinning. The electrospun scaffolds were characterized by scanning electron microscope with X-ray elemental analysis, atomic force microcopy, differential scanning calorimetry, and contact angle analysis for optimizing the effective parameters. Fiber formation with uniform diameter and bead-free structure was obtained. Scaffold surface roughness increased from 100&nbsp;nm for PCL to 440&nbsp;nm for PCL/DCPD. DSC analysis showed the effects of DCPD on thermal stability of composite scaffold and the results of contact angle evaluation indicate improved hydrophilicity and ability of water absorption of PCL/DCPD composite fibers as compared to PCL fibers. MTT assay indicated lack of toxicity for human gingival fibroblast (HGF) cells after cell seeding on scaffold. Also, the composite scaffold can improve cell viability by helping their growth on its surface. So it can be concluded that by engineering the electrospinning parameters we can fabricate a PCL/DCPD composite scaffold for tissue engineering applications.<br />
DOI: 10.1007/s12033-019-00168-4 PMID: 30887276<br />
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[5]. Polymers (Basel). 2017 Jan 28;9(2):42. doi: 10.3390/polym9020042.<br />
Crystallization of Poly(&epsilon;-caprolactone) in Poly(vinylidene fluoride)/Poly(&epsilon;-caprolactone) Blend.<br />
Kong Y(1), Ma Y(2), Lei L(3), Wang X(4), Wang H(5).<br />
Author information: (1)Shaanxi University of Science and Technology, Xi&#39;an 710021, Shaanxi, China. [email protected]. (2)Shaanxi University of Science and Technology, Xi&#39;an 710021, Shaanxi, China. [email protected]. (3)Shaanxi University of Science and Technology, Xi&#39;an 710021, Shaanxi, China. [email protected]. (4)Shaanxi University of Science and Technology, Xi&#39;an 710021, Shaanxi, China. [email protected]. (5)Shaanxi University of Science and Technology, Xi&#39;an 710021, Shaanxi, China. [email protected].<br />
The crystallization behavior of poly(&epsilon;-caprolactone) (PCL) in a poly(vinylidene fluoride) (PVDF)/PCL blend as well as on a highly orientated PVDF substrate was studied by means of POM, DSC and TEM. The results show that the miscibility of the PVDF/PCL blend and the spherulitic morphology of PVDF varies with the blend ratio. For all the compositions, the pre-existing PVDF crystals accelerated the crystallization of PCL because the PVDF exhibits very strong nucleation ability toward PCL as reflected by the occurrence of heteroepitaxy and the transcrystallization of PBA on the PVDF substrate. This is associated with the perfect lattice matching between the PBA and PVDF crystals.<br />
DOI: 10.3390/polym9020042 PMCID: PMC6432374 PMID: 30970722

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