Caprolactam (CED0005350)

Record Information
Version1.0
Creation Date2016-05-19 01:35:08 UTC
Update Date2026-08-23 05:25:15 UTC
Accession NumberCHEM004115
Identification
Common NameCaprolactam
ClassSmall Molecule
Description
Caprolactam belongs to the caprolactams, a subclass of lactams within the organic compounds. This organoheterocyclic compound has the chemical formula $\text{C}_6\text{H}_{11}\text{NO}$ and an average molecular weight of 113.16 g/mol. In industrial applications, it serves as a monomer, filler, flavouring and nutrient, and as a degradant or impurity. The compound is released from polyamide and is used in polypropylene, low-density polyethylene, and high-density polyethylene, though its presence in polyurethane, polyacrylonitrile, and polyethylene terephthalate remains inconclusive. Caprolactam is found in or released from 38 recorded sources. These include building and construction materials such as tents or canopies, ladders, stairs and ramps, and fencing. It is also associated with electrical and electronic equipment, including communication cables or conductors, coils, antennas, adjustable resistors, and auxiliary devices. Within household cleaning and consumer products, it is found in bleaching agents, ash trays, perfumes within detergents and soaps, cigar cigarettes, and non-electric simulated smoking devices. In the context of food, food processing, and cookware, it is linked to food preservation, processing meats, food contact materials, and fermentation processes for beer. Additionally, it is recorded in drinking water and indoor air. Human exposure to caprolactam occurs through touch, oral, and inhalation routes.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
2-KetohexamethyleneimineChEBI
2-OxohexamethylenimineChEBI
6-CaprolactamChEBI
Aminocaproic lactamChEBI
CaprolactamChEBI
Hexahydro-2H-azepin-2-oneChEBI
KaprolaktamChEBI
Hexahydro 2H azepin 2 oneMeSH
Lactam, aminocaproicMeSH
Chemical FormulaC6H11NO
Average Molecular Mass113.158 g/mol
Monoisotopic Mass113.084 g/mol
CAS Registry Number105-60-2
IUPAC Nameazepan-2-one
Traditional Namecaprolactam
SMILESO=C1CCCCCN1
InChI IdentifierInChI=1S/C6H11NO/c8-6-4-2-1-3-5-7-6/h1-5H2,(H,7,8)
InChI KeyJBKVHLHDHHXQEQ-UHFFFAOYSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassCaprolactams
Direct ParentCaprolactams
Alternative Parents
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
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility156 g/LALOGPS
logP-0.08ALOGPS
logP0.31ChemAxon
logS0.14ALOGPS
pKa (Strongest Acidic)14.99ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.1 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity31.46 m³·mol⁻¹ChemAxon
Polarizability12.47 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0bt9-9200000000-0d6a682cae74fe53b7aaNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-2900000000-4730d2250020d7d304f5Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0bt9-9200000000-0d6a682cae74fe53b7aaNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-2900000000-4730d2250020d7d304f5Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-004l-9000000000-3b9e8e693efae76c21ceNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-2900000000-6c04be24bf66efac0e43Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-7900000000-58735f4c6778ab4cabefNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9000000000-9a1f4e5049dfe1ca424aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-1900000000-569b06e2f2b66a34120cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-6900000000-bb17447adbc5fe91e767Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-ebcbd48044e8ad6be333Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0900000000-7ca3d0aa73039ede6ec3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-5900000000-c745f90858c739aabdf9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9100000000-41302a19adfdf93d5710Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-1900000000-65f6e161437cff6243f0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-9500000000-c8b713877673d938ca67Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052f-9000000000-9585d6a51197032889c3Not AvailableView Spectrum
MSMS Spectrumsplash10-053u-9100000000-2d9059914505fc652476Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1745.0Log mg/kg[980:3100]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
19Indoor airAir, dust & atmospheric transportNot Available
115Drinking waterDrinking water & water supplyNot Available
233BrushesPersonal care & cosmeticsNot Available
494Food contact materialsFood, food processing & cookwareNot Available
496FencingBuilding & ConstructionNot Available
498LaddersBuilding & ConstructionNot Available
500Stairs And RampsBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
504Adjustable ResistorsElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
508CoilsElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
512ContactsElectrical & Electronic EquipmentNot Available
513Cores Yokes Or ArmaturesElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
526LoudspeakersElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
554Ash TraysHousehold cleaning & consumer productsNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
585Canoes And KayaksMarine, shipping & aquacultureNot Available
589Life BuoysMarine, shipping & aquacultureNot Available
591LifeboatsMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
631Anthraquinone DyesTextiles, leather & furnishingsNot Available
632ApparelTextiles, leather & furnishingsNot Available
633Azo DyesTextiles, leather & furnishingsNot Available
635ButtonsTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
645Inorganic FibresTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
648Nitro DyesTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
661UmbrellasTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Poly [ADP-ribose] polymerase 1 structureClick to view 3D structurePoly [ADP-ribose] polymerase 1P09874HumansPredicted (SEA)3658.52
Glycogen synthase kinase-3 beta structureClick to view 3D structureGlycogen synthase kinase-3 betaP49841HumansPredicted (SEA)7177.31
Protein mono-ADP-ribosyltransferase PARP10 structureClick to view 3D structureProtein mono-ADP-ribosyltransferase PARP10Q53GL7HumansPredicted (SEA)2031.24
LIM domain kinase 1 structureClick to view 3D structureLIM domain kinase 1P53667HumansPredicted (SEA)7047.77
Protein mono-ADP-ribosyltransferase PARP11 structureClick to view 3D structureProtein mono-ADP-ribosyltransferase PARP11Q9NR21HumansPredicted (SEA)867.63
Cell division cycle 7-related protein kinase structureClick to view 3D structureCell division cycle 7-related protein kinaseO00311HumansPredicted (SEA)6887.71
Serine/threonine-protein kinase Chk1 structureClick to view 3D structureSerine/threonine-protein kinase Chk1O14757HumansPredicted (SEA)7362.59
Dual specificity protein kinase CLK4 structureClick to view 3D structureDual specificity protein kinase CLK4Q9HAZ1HumansPredicted (SEA)7294.16
Click to view 3D structureMu-type opioid receptorP33535Rattus norvegicusPredicted (SEA)4217.79
Click to view 3D structureDelta-type opioid receptorP33533Rattus norvegicusPredicted (SEA)4037.65
Growth factor receptor-bound protein 7 structureClick to view 3D structureGrowth factor receptor-bound protein 7Q14451HumansPredicted (SEA)94.4311
Protein cereblon structureClick to view 3D structureProtein cereblonQ96SW2HumansPredicted (SEA)856.108
Dual specificity tyrosine-phosphorylation-regulated kinase 1A structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 1AQ13627HumansPredicted (SEA)7406.19
Cyclin-dependent kinase 2 structureClick to view 3D structureCyclin-dependent kinase 2P24941HumansPredicted (SEA)7466.83
MAP kinase-activated protein kinase 2 structureClick to view 3D structureMAP kinase-activated protein kinase 2P49137HumansPredicted (SEA)7354.88
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)7557.14
Serine/threonine-protein kinase Nek2 structureClick to view 3D structureSerine/threonine-protein kinase Nek2P51955HumansPredicted (SEA)7346.63
Proto-oncogene tyrosine-protein kinase Src structureClick to view 3D structureProto-oncogene tyrosine-protein kinase SrcP12931HumansPredicted (SEA)7528.02
Aurora kinase A structureClick to view 3D structureAurora kinase AO14965HumansPredicted (SEA)7447.68
cAMP-dependent protein kinase catalytic subunit alpha structureClick to view 3D structurecAMP-dependent protein kinase catalytic subunit alphaP17612HumansPredicted (SEA)7444.64
Rho-associated protein kinase 2 structureClick to view 3D structureRho-associated protein kinase 2O75116HumansPredicted (SEA)7479.44
Serine/threonine-protein kinase Chk2 structureClick to view 3D structureSerine/threonine-protein kinase Chk2O96017HumansPredicted (SEA)7265.75
Serine/threonine-protein kinase PLK1 structureClick to view 3D structureSerine/threonine-protein kinase PLK1P53350HumansPredicted (SEA)7409.92
Mitogen-activated protein kinase 1 structureClick to view 3D structureMitogen-activated protein kinase 1P28482HumansPredicted (SEA)7498.13
Interleukin-1 receptor-associated kinase 4 structureClick to view 3D structureInterleukin-1 receptor-associated kinase 4Q9NWZ3HumansPredicted (SEA)7361.11
Concentrations
StatusValueUnitSample LocationReference
External Links
DrugBank IDNot Available
HMDB IDHMDB0062769
FooDB IDFDB009075
Phenol Explorer IDNot Available
KNApSAcK IDC00000318
BiGG IDNot Available
BioCyc IDCPD-883
METLIN IDNot Available
PDB IDICC
Wikipedia LinkCaprolactam
Chemspider ID7480
ChEBI ID28579
PubChem Compound ID7768
Kegg Compound IDC06593
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17161908
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=2263224
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=9688819