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Record Information
Version2.0
Creation Date2012-08-03 14:57:55 -0600
Update Date2015-09-13 15:15:32 -0600
Secondary Accession Numbers
  • ECMDB21405
Identification
Name:Diethanolamine
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
Thumb
Synonyms:
  • 2,2'-Dihydroxydiethylamine
  • 2,2'-Iminobis
  • 2,2'-Iminobisethanol
  • 2,2'-Iminodi-1-ethanol
  • 2,2'-Iminodiethanol
  • 2,2'Iminobisethanol
  • 2-(2-Hydroxyethylamino)ethanol
  • 2-[(2-Hydroxyethyl)amino]ethanol
  • Aliphatic amine
  • B,b'-Dihydroxydiethylamine
  • Bis(2-hydroxyethyl)amine
  • Bis(2-hydroxyethyl)tallow amine oxide
  • Bis(hydroxyethyl)amine
  • Bis-2-hydroxyethylamine
  • DEA
  • DEOA
  • Di(2-hydroxyethyl)amine
  • Di(b-hydroxyethyl)amine
  • Di(beta-hydroxyethyl)amine
  • Di(β-hydroxyethyl)amine
  • Diaethanolamin
  • Diethanolamin
  • Diethylolamine
  • Dihydroxyethyl tallowamine oxide
  • Diolamine
  • H2dea
  • Iminodiethanol
  • N,N'-Iminodiethanol
  • N,N-Bis(2-hydroxyethyl)amine
  • N,N-Di(hydroxyethyl)amine
  • N,N-Diethanolamine
  • N-Ethylethanamine
  • Niax DEOA-LF
Chemical Formula:C4H11NO2
Weight:Average: 105.1356
Monoisotopic: 105.078978601
InChI Key:ZBCBWPMODOFKDW-UHFFFAOYSA-N
InChI:InChI=1S/C4H11NO2/c6-3-1-5-2-4-7/h5-7H,1-4H2
CAS number:111-42-2
IUPAC Name:2-[(2-hydroxyethyl)amino]ethan-1-ol
Traditional IUPAC Name:diethanolamine
SMILES:OCCNCCO
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
Physical Properties
State:Solid
Charge:1
Melting point:28 °C
Experimental Properties:
PropertyValueSource
Water Solubility:1000 mg/mL at 20 oC [DOW CHEMICAL COMPANY (1980)]PhysProp
LogP:-1.43 [HANSCH,C ET AL. (1995)]PhysProp
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
20± 0 uMBW2511348 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L GlucoStationary Phase, glucose limitedBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h37 oCPMID: 17379776
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9430000000-79f7d3e25a715793917aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001j-1900000000-bd0861145364bd684950View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0159-5940000000-ebe5523dad23d3dc2391View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9430000000-79f7d3e25a715793917aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-5940000000-ebe5523dad23d3dc2391View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001j-1900000000-bd0861145364bd684950View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05am-9000000000-7eea9eaa21af51853910View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dj-9800000000-3db6474ab842a5d03fb3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4r-9700000000-6ae8b510d6cd7e4ba8d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0005-9000000000-d0e266aca011203c762aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0005-9000000000-b924f709a47552d0afc1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a4i-0900000000-11bfee15df34ebc320e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-05g0-9200000000-39da135b20d99fa34636View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00dm-9000000000-74add71de850cb4c8e2dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0005-9000000000-794a61320b2e8c5a8970View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0007-9000000000-af9eeb72884d4847a0a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0a4i-0900000000-cd466740723ff131d76fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-0900000000-a5ca41984423de95ef78View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-05g0-9200000000-626e5d5103e3012c611eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dm-9000000000-74add71de850cb4c8e2dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0005-9000000000-794a61320b2e8c5a8970View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0007-9000000000-be35c09bcc6cd8c79f05View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-cd466740723ff131d76fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0abi-9500000000-ee4dbde39d4c97f1cae9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-03k9-9000000000-e03c494989bc56f168eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03di-9000000000-122a3a485bc0a1bfded4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0007-9000000000-939cd379fb164bb8a094View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2900000000-c1dc229350e5cf19c090View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9500000000-b3018e09980645272c12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9000000000-ae6bfcca013a433a0a24View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3900000000-d6387d7e1686e32ad49aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-8900000000-66c6a6cce5f90a2cdb52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-9000000000-7e1da753c608954b27eeView in MoNA
MSMass Spectrum (Electron Ionization)splash10-05fr-9000000000-362b201708dabf55f01bView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
  • 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
  • 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
  • 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
  • Zeisel SH, DaCosta KA, Fox JG: Endogenous formation of dimethylamine. Biochem J. 1985 Dec 1;232(2):403-8. Pubmed: 4091797
Synthesis Reference:Peschel, 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)
External Links:
ResourceLink
CHEBI ID28123
HMDB IDHMDB04437
Pubchem Compound ID8113
Kegg IDC06772
ChemSpider ID13835604
WikipediaDiethanolamine
BioCyc IDNot Available