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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-08-13 18:57:19 UTC
Update Date2020-03-04 16:53:19 UTC
HMDB IDHMDB0004437
Secondary Accession Numbers
  • HMDB0003091
  • HMDB03091
  • HMDB04437
Metabolite Identification
Common NameDiethanolamine
DescriptionDiethanolamine, often abbreviated as DEA, is an organic chemical compound which is both a secondary amine and a dialcohol. A dialcohol has two hydroxyl groups in its molecule. Like other amines, diethanolamine acts as a weak base. Diethanolamine is widely used in the preparation of diethanolamides and diethanolamine salts of long-chain fatty acids that are formulated into soaps and surfactants used in liquid laundry and dishwashing detergents, cosmetics, shampoos, and hair conditioners. Diethanolamine is also used in textile processing, in industrial gas purification to remove acid gases, as an anticorrosion agent in metalworking fluids, and in preparations of agricultural chemicals. Aqueous diethanolamine solutions are used as solvents for numerous drugs that are administered intravenously.
Structure
Data?1583340799
Synonyms
ValueSource
Bis-(2-hydroxy-ethyl)-amineChEBI
DiolamineChEBI
H2dEaChEBI
N,N-Di(hydroxyethyl)amineChEBI
2,2'-DihydroxydiethylamineHMDB
2,2'-IminobisHMDB
2,2'-IminobisethanolHMDB
2,2'-Iminodi-1-ethanolHMDB
2,2'-IminodiethanolHMDB
2,2'IminobisethanolHMDB
2-(2-Hydroxyethylamino)ethanolHMDB
2-[(2-Hydroxyethyl)amino]ethanolHMDB
Aliphatic amineHMDB
Bis(2-hydroxyethyl)amineHMDB
Bis(2-hydroxyethyl)tallow amine oxideHMDB
Bis(hydroxyethyl)amineHMDB
Bis-2-hydroxyethylamineHMDB
DEAHMDB
Di(2-hydroxyethyl)amineHMDB
Di(beta-hydroxyethyl)amineHMDB
DiaethanolaminHMDB
DiethanolaminHMDB
DiethylolamineHMDB
IminodiethanolHMDB
N,N'-IminodiethanolHMDB
N,N-Bis(2-hydroxyethyl)amineHMDB
N,N-DiethanolamineHMDB
Di(β-hydroxyethyl)amineHMDB
DiethanolamineHMDB
N,N-Di(2-hydroxyethyl)amineHMDB
Chemical FormulaC4H11NO2
Average Molecular Weight105.1356
Monoisotopic Molecular Weight105.078978601
IUPAC Name2-[(2-hydroxyethyl)amino]ethan-1-ol
Traditional Namediethanolamine
CAS Registry Number111-42-2
SMILES
OCCNCCO
InChI Identifier
InChI=1S/C4H11NO2/c6-3-1-5-2-4-7/h5-7H,1-4H2
InChI KeyZBCBWPMODOFKDW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct Parent1,2-aminoalcohols
Alternative Parents
Substituents
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Environmental role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point28 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 20 °CNot Available
LogP-1.43HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility466 g/LALOGPS
logP-1.4ALOGPS
logP-1.6ChemAxon
logS0.65ALOGPS
pKa (Strongest Acidic)15.3ChemAxon
pKa (Strongest Basic)9.26ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area52.49 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity27.28 m³·mol⁻¹ChemAxon
Polarizability11.63 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9430000000-79f7d3e25a715793917aSpectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001j-1900000000-bd0861145364bd684950Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0159-5940000000-ebe5523dad23d3dc2391Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9430000000-79f7d3e25a715793917aSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-5940000000-ebe5523dad23d3dc2391Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001j-1900000000-bd0861145364bd684950Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05am-9000000000-7eea9eaa21af51853910Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dj-9800000000-3db6474ab842a5d03fb3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4r-9700000000-6ae8b510d6cd7e4ba8d0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0005-9000000000-d0e266aca011203c762aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0005-9000000000-b924f709a47552d0afc1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a4i-0900000000-11bfee15df34ebc320e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-05g0-9200000000-39da135b20d99fa34636Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00dm-9000000000-74add71de850cb4c8e2dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0005-9000000000-794a61320b2e8c5a8970Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0007-9000000000-af9eeb72884d4847a0a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0a4i-0900000000-cd466740723ff131d76fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-0900000000-a5ca41984423de95ef78Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-05g0-9200000000-626e5d5103e3012c611eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dm-9000000000-74add71de850cb4c8e2dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0005-9000000000-794a61320b2e8c5a8970Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0007-9000000000-be35c09bcc6cd8c79f05Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-cd466740723ff131d76fSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0abi-9500000000-ee4dbde39d4c97f1cae9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2900000000-c1dc229350e5cf19c090Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9500000000-b3018e09980645272c12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9000000000-ae6bfcca013a433a0a24Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3900000000-d6387d7e1686e32ad49aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-8900000000-66c6a6cce5f90a2cdb52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-9000000000-7e1da753c608954b27eeSpectrum
MSMass Spectrum (Electron Ionization)splash10-05fr-9000000000-362b201708dabf55f01bSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Feces
  • Urine
Tissue Locations
  • Thyroid Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Not AvailableNot AvailableNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023372
KNApSAcK IDNot Available
Chemspider ID13835604
KEGG Compound IDC06772
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiethanolamine
METLIN ID3239
PubChem Compound8113
PDB IDNot Available
ChEBI ID28123
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferencePeschel, Werner; Hildebrandt, Axel; Bessling, Bernd. Continuous process for the synthesis of monoethanolamine, diethanolamine and triethanolamine via the addition reaction of ammonia with ethylene oxide in the presence of water as a catalyst. Eur. Pat. Appl. (2003), 11 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Mathews JM, deCosta K, Thomas BF: Lauramide diethanolamine absorption, metabolism, and disposition in rats and mice after oral, intravenous, and dermal administration. Drug Metab Dispos. 1996 Jul;24(7):702-10. [PubMed:8818565 ]
  2. Zeisel SH, DaCosta KA, Fox JG: Endogenous formation of dimethylamine. Biochem J. 1985 Dec 1;232(2):403-8. [PubMed:4091797 ]
  3. Authors unspecified: NTP Toxicology and Carcinogenesis Studies of Lauric Acid Diethanolamine Condensate (CAS NO. 120-40-1) in F344/N Rats and B6C3F1 Mice (Dermal Studies). Natl Toxicol Program Tech Rep Ser. 1999 Jul;480:1-200. [PubMed:12571683 ]
  4. Authors unspecified: NTP Toxicology and Carcinogenesis Studies of Diethanolamine (CAS No. 111-42-2) in F344/N Rats and B6C3F1 Mice (Dermal Studies). Natl Toxicol Program Tech Rep Ser. 1999 Jul;478:1-212. [PubMed:12571685 ]