Record Information |
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Version | 1.0 |
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Created at | 2020-11-23 19:39:40 UTC |
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Updated at | 2021-08-19 23:59:19 UTC |
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NP-MRD ID | NP0002758 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Epsilon-caprolactone |
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Provided By | BMRB |
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Description | Epsilon-Caprolactone, also known as 6-hexanolide or 1-oxa-2-oxocycloheptane, belongs to the class of organic compounds known as lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. Epsilon-Caprolactone is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. It was first documented in 2008 (PMID: 17984079). Based on a literature review a significant number of articles have been published on epsilon-Caprolactone (PMID: 21447597) (PMID: 24453135) (PMID: 34378381) (PMID: 34372160). |
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Structure | InChI=1S/C6H10O2/c7-6-4-2-1-3-5-8-6/h1-5H2 |
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Synonyms | Value | Source |
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1,6-Hexanolide | ChEBI | 1-Oxa-2-oxocycloheptane | ChEBI | 2-Oxacycloheptanone | ChEBI | 2-Oxepanone | ChEBI | 2-Oxohexamethylene oxide | ChEBI | 6-Hexanolactone | ChEBI | 6-Hexanolide | ChEBI | 6-Hydroxyhexanoic acid lactone | ChEBI | 6-Hydroxyhexanoic acid, epsilon-lactone | ChEBI | Caprolactone | ChEBI | epsilon-Caprolactone monomer | ChEBI | Hexan-6-olide | ChEBI | Hexanoic acid, epsilon-lactone | ChEBI | Hexano-6-lactone | Kegg | 6-Hydroxyhexanoate lactone | Generator | 6-Hydroxyhexanoate, epsilon-lactone | Generator | Hexanoate, epsilon-lactone | Generator | epsilon-Captolactamium hydrogen sulfate | HMDB | epsilon-Caprolactone | ChEBI |
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Chemical Formula | C6H10O2 |
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Average Mass | 114.1424 Da |
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Monoisotopic Mass | 114.06808 Da |
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IUPAC Name | oxepan-2-one |
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Traditional Name | caprolactone |
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CAS Registry Number | Not Available |
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SMILES | O=C1CCCCCO1 |
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InChI Identifier | InChI=1S/C6H10O2/c7-6-4-2-1-3-5-8-6/h1-5H2 |
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InChI Key | PAPBSGBWRJIAAV-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Not Available |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Lactones |
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Sub Class | Not Available |
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Direct Parent | Lactones |
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Alternative Parents | Not Available |
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Substituents | Not Available |
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Properties | |
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Predicted Properties | |
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External Links |
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HMDB ID | HMDB0060476 |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 9972 |
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KEGG Compound ID | C01880 |
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BioCyc ID | CPD-101 |
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BiGG ID | Not Available |
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Wikipedia Link | Caprolactone |
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METLIN ID | Not Available |
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PubChem Compound | 10401 |
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PDB ID | Not Available |
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ChEBI ID | 17915 |
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Good Scents ID | rw1242691 |
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References |
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General References | - Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
- Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
- Romain DC, Williams CK: Chemoselective polymerization control: from mixed-monomer feedstock to copolymers. Angew Chem Int Ed Engl. 2014 Feb 3;53(6):1607-10. doi: 10.1002/anie.201309575. Epub 2014 Jan 22. [PubMed:24453135 ]
- Rungrod A, Kapanya A, Punyodom W, Molloy R, Meerak J, Somsunan R: Synthesis of Poly(epsilon-caprolactone) Diacrylate for Micelle-Cross-Linked Sodium AMPS Hydrogel for Use as Controlled Drug Delivery Wound Dressing. Biomacromolecules. 2021 Aug 11. doi: 10.1021/acs.biomac.1c00683. [PubMed:34378381 ]
- Vollrath A, Kretzer C, Beringer-Siemers B, Shkodra B, Czaplewska JA, Bandelli D, Stumpf S, Hoeppener S, Weber C, Werz O, Schubert US: Effect of Crystallinity on the Properties of Polycaprolactone Nanoparticles Containing the Dual FLAP/mPEGS-1 Inhibitor BRP-187. Polymers (Basel). 2021 Jul 31;13(15). pii: polym13152557. doi: 10.3390/polym13152557. [PubMed:34372160 ]
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