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Showing Compound Caprolactam (FDB009075)

Record Information
Version1.0
Creation date2010-04-08 22:08:24 UTC
Update date2019-11-26 03:03:25 UTC
Primary IDFDB009075
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCaprolactam
DescriptionCaprolactam, 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 .
CAS Number105-60-2
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
2-KetohexamethyleneimineChEBI
2-OxohexamethylenimineChEBI
6-CaprolactamChEBI
Aminocaproic lactamChEBI
CaprolactamChEBI
Hexahydro-2H-azepin-2-oneChEBI
KaprolaktamChEBI
Hexahydro 2H azepin 2 oneMeSH
Lactam, aminocaproicMeSH
1-Aza-2-cycloheptanonebiospider
1,6-Hexalactambiospider
1,6-Hexolactambiospider
2-Azacycloheptanonebiospider
2-Azepanonebiospider
2-Ketohexamethyleniminebiospider
2-Oxohexamethyleneiminebiospider
2-Perhydroazepinonebiospider
2H-Azepin-2-one, hexahydro-biospider
2H-Azepin-7-one, hexahydro-biospider
6-amino-hexanoic acid lactambiospider
6-Aminocaproic acid lactambiospider
6-Aminohexanoic acid cyclic lactambiospider
6-Aminohexanoic acid lactambiospider
6-Hexanelactambiospider
Akulonbiospider
Alkamidbiospider
Amilan cm 1001biospider
Aza-2-cycloheptanonebiospider
azepan-2-onebiospider
Bonamidbiospider
Capran 77Cbiospider
Caprolactam monomerbiospider
Caprolattamebiospider
Caprolon vbiospider
Capronbiospider
Chemlonbiospider
cis-Hexahydro-2-azepinonebiospider
Cyclohexanone iso-oximebiospider
Danamidbiospider
Durethan BKbiospider
E-caprolactambiospider
E-caprolactumbiospider
Epsilon-caprolactambiospider
Ertalon 6sabiospider
Extrom 6Nbiospider
Gamma-caprolactambiospider
Grilonbiospider
Hexahydro-2-azepinonebiospider
Hexannic acidbiospider
hexanoic acid-6-amino-lactambiospider
Hexanolactambiospider
Hexanone isoximebiospider
Itamidbiospider
Kaprolitbiospider
Kaprolonbiospider
Kaprominebiospider
Kapronbiospider
Maranyl F 114biospider
Metamidbiospider
Miramid H 2biospider
Nipro (I)biospider
Nylon A1035sfbiospider
Omega-caprolactumbiospider
Orgamid rmnocdbiospider
Orgamidebiospider
Perhydroazepin-2-onebiospider
Plaskin 8200biospider
Plaskon 201biospider
Polyamide pk 4biospider
Relon pbiospider
Renyl MVbiospider
Sipas 60biospider
Spencer 401biospider
Spencer 601biospider
Steelonbiospider
Stilonbiospider
Stylonbiospider
Tarlon x-abiospider
Tarlon XBbiospider
Tarnamid T 2biospider
Tarnamid T 27biospider
TNK 2G5biospider
Torayca N 6biospider
U-caprolactambiospider
Ultramid BMKbiospider
Vidlonbiospider
Widlonbiospider
Zytel 211biospider
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
Chemical FormulaC6H11NO
IUPAC nameazepan-2-one
InChI IdentifierInChI=1S/C6H11NO/c8-6-4-2-1-3-5-7-6/h1-5H2,(H,7,8)
InChI KeyJBKVHLHDHHXQEQ-UHFFFAOYSA-N
Isomeric SMILESO=C1CCCCCN1
Average Molecular Weight113.1576
Monoisotopic Molecular Weight113.084063979
Classification
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
Ontology
Disposition

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point69.3 oC
Boiling PointNot Available
Experimental Water Solubility772 mg/mL at 10 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-053u-9100000000-2d9059914505fc6524762014-10-20View Spectrum
GC-MSCaprolactam, non-derivatized, GC-MS Spectrumsplash10-0bt9-9200000000-0d6a682cae74fe53b7aaSpectrum
GC-MSCaprolactam, non-derivatized, GC-MS Spectrumsplash10-00di-2900000000-4730d2250020d7d304f5Spectrum
GC-MSCaprolactam, non-derivatized, GC-MS Spectrumsplash10-0bt9-9200000000-0d6a682cae74fe53b7aaSpectrum
GC-MSCaprolactam, non-derivatized, GC-MS Spectrumsplash10-00di-2900000000-4730d2250020d7d304f5Spectrum
Predicted GC-MSCaprolactam, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004l-9000000000-3b9e8e693efae76c21ceSpectrum
Predicted GC-MSCaprolactam, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCaprolactam, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2900000000-6c04be24bf66efac0e432016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-7900000000-58735f4c6778ab4cabef2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-9a1f4e5049dfe1ca424a2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-569b06e2f2b66a34120c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-6900000000-bb17447adbc5fe91e7672016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-ebcbd48044e8ad6be3332016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-7ca3d0aa73039ede6ec32021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-5900000000-c745f90858c739aabdf92021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-41302a19adfdf93d57102021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1900000000-65f6e161437cff6243f02021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9500000000-c8b713877673d938ca672021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-9585d6a51197032889c32021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC06593
Pubchem Compound ID7768
Pubchem Substance IDNot Available
ChEBI ID28579
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS ID502
Dr. Duke IDHEXAHYDRO-2H-AZEPIN-2-ONE
BIGG IDNot Available
KNApSAcK IDC00000318
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1242681
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
allelochemicDUKE
herbicide24527 A substance used to destroy plant pests.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
amine
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spicy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. 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
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
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.