Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:08:24 UTC |
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Update date | 2019-11-26 03:03:25 UTC |
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Primary ID | FDB009075 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Caprolactam |
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Description | Caprolactam, also known as aminocaproic lactam or hexahydro-2h-azepin-2-one, is a member of the class of compounds known as caprolactams. Caprolactams are cyclic amides of caproic acid. Caproic acid is the carboxylic acid derived from hexane with the general formula C5H11COOH. Caprolactam is soluble (in water) and a very weakly acidic compound (based on its pKa). Caprolactam is an amine, bitter, and spicy tasting compound found in sunflower, which makes caprolactam a potential biomarker for the consumption of this food product. Caprolactam (CPL) is an organic compound with the formula (CH2)5C(O)NH. This colourless solid is a lactam (a cyclic amide) of caproic acid. Global demand for this compound is approximately 5 million tons per year, and the vast majority is used to make Nylon 6 filament, fiber, and plastics . |
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CAS Number | 105-60-2 |
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Structure | |
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Synonyms | Synonym | Source |
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2-Ketohexamethyleneimine | ChEBI | 2-Oxohexamethylenimine | ChEBI | 6-Caprolactam | ChEBI | Aminocaproic lactam | ChEBI | Caprolactam | ChEBI | Hexahydro-2H-azepin-2-one | ChEBI | Kaprolaktam | ChEBI | Hexahydro 2H azepin 2 one | MeSH | Lactam, aminocaproic | MeSH | 1-Aza-2-cycloheptanone | biospider | 1,6-Hexalactam | biospider | 1,6-Hexolactam | biospider | 2-Azacycloheptanone | biospider | 2-Azepanone | biospider | 2-Ketohexamethylenimine | biospider | 2-Oxohexamethyleneimine | biospider | 2-Perhydroazepinone | biospider | 2H-Azepin-2-one, hexahydro- | biospider | 2H-Azepin-7-one, hexahydro- | biospider | 6-amino-hexanoic acid lactam | biospider | 6-Aminocaproic acid lactam | biospider | 6-Aminohexanoic acid cyclic lactam | biospider | 6-Aminohexanoic acid lactam | biospider | 6-Hexanelactam | biospider | Akulon | biospider | Alkamid | biospider | Amilan cm 1001 | biospider | Aza-2-cycloheptanone | biospider | azepan-2-one | biospider | Bonamid | biospider | Capran 77C | biospider | Caprolactam monomer | biospider | Caprolattame | biospider | Caprolon v | biospider | Capron | biospider | Chemlon | biospider | cis-Hexahydro-2-azepinone | biospider | Cyclohexanone iso-oxime | biospider | Danamid | biospider | Durethan BK | biospider | E-caprolactam | biospider | E-caprolactum | biospider | Epsilon-caprolactam | biospider | Ertalon 6sa | biospider | Extrom 6N | biospider | Gamma-caprolactam | biospider | Grilon | biospider | Hexahydro-2-azepinone | biospider | Hexannic acid | biospider | hexanoic acid-6-amino-lactam | biospider | Hexanolactam | biospider | Hexanone isoxime | biospider | Itamid | biospider | Kaprolit | biospider | Kaprolon | biospider | Kapromine | biospider | Kapron | biospider | Maranyl F 114 | biospider | Metamid | biospider | Miramid H 2 | biospider | Nipro (I) | biospider | Nylon A1035sf | biospider | Omega-caprolactum | biospider | Orgamid rmnocd | biospider | Orgamide | biospider | Perhydroazepin-2-one | biospider | Plaskin 8200 | biospider | Plaskon 201 | biospider | Polyamide pk 4 | biospider | Relon p | biospider | Renyl MV | biospider | Sipas 60 | biospider | Spencer 401 | biospider | Spencer 601 | biospider | Steelon | biospider | Stilon | biospider | Stylon | biospider | Tarlon x-a | biospider | Tarlon XB | biospider | Tarnamid T 2 | biospider | Tarnamid T 27 | biospider | TNK 2G5 | biospider | Torayca N 6 | biospider | U-caprolactam | biospider | Ultramid BMK | biospider | Vidlon | biospider | Widlon | biospider | Zytel 211 | biospider |
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Predicted Properties | |
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Chemical Formula | C6H11NO |
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IUPAC name | azepan-2-one |
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InChI Identifier | InChI=1S/C6H11NO/c8-6-4-2-1-3-5-7-6/h1-5H2,(H,7,8) |
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InChI Key | JBKVHLHDHHXQEQ-UHFFFAOYSA-N |
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Isomeric SMILES | O=C1CCCCCN1 |
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Average Molecular Weight | 113.1576 |
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Monoisotopic Molecular Weight | 113.084063979 |
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Classification |
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Description | Belongs to the class of organic compounds known as caprolactams. These are cyclic amides of caproic acid. Caproic acid is the carboxylic acid derived from hexane with the general formula C5H11COOH. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Lactams |
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Sub Class | Caprolactams |
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Direct Parent | Caprolactams |
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Alternative Parents | |
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Substituents | - Caprolactam
- Azepane
- Secondary carboxylic acid amide
- Carboxamide group
- Azacycle
- Carboxylic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Biological location: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | 69.3 oC | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 772 mg/mL at 10 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-053u-9100000000-2d9059914505fc652476 | 2014-10-20 | View Spectrum | GC-MS | Caprolactam, non-derivatized, GC-MS Spectrum | splash10-0bt9-9200000000-0d6a682cae74fe53b7aa | Spectrum | GC-MS | Caprolactam, non-derivatized, GC-MS Spectrum | splash10-00di-2900000000-4730d2250020d7d304f5 | Spectrum | GC-MS | Caprolactam, non-derivatized, GC-MS Spectrum | splash10-0bt9-9200000000-0d6a682cae74fe53b7aa | Spectrum | GC-MS | Caprolactam, non-derivatized, GC-MS Spectrum | splash10-00di-2900000000-4730d2250020d7d304f5 | Spectrum | Predicted GC-MS | Caprolactam, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-004l-9000000000-3b9e8e693efae76c21ce | Spectrum | Predicted GC-MS | Caprolactam, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Caprolactam, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-2900000000-6c04be24bf66efac0e43 | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-7900000000-58735f4c6778ab4cabef | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-9a1f4e5049dfe1ca424a | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-1900000000-569b06e2f2b66a34120c | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-6900000000-bb17447adbc5fe91e767 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-ebcbd48044e8ad6be333 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0900000000-7ca3d0aa73039ede6ec3 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-5900000000-c745f90858c739aabdf9 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9100000000-41302a19adfdf93d5710 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-1900000000-65f6e161437cff6243f0 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-9500000000-c8b713877673d938ca67 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9000000000-9585d6a51197032889c3 | 2021-09-25 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C06593 |
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Pubchem Compound ID | 7768 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 28579 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | 502 |
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Dr. Duke ID | HEXAHYDRO-2H-AZEPIN-2-ONE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00000318 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | rw1242681 |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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allelochemic | | | DUKE | herbicide | 24527 | A substance used to destroy plant pests. | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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amine |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| spicy |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| bitter |
- Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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