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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-08-13 18:57:19 UTC
Update Date2019-03-14 18:03:05 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?1547234284
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
Dihydroxyethyl tallowamine oxideHMDB
IminodiethanolHMDB
N,N'-iminodiethanolHMDB
N,N-Bis(2-hydroxyethyl)amineHMDB
N,N-DiethanolamineHMDB
Niax deoa-LFHMDB
Diethanolamine fumarateHMDB
Diethanolamine maleateHMDB
Diethanolamine sulfate (1:1)HMDB
Diethanolamine sulfiteHMDB
Diethanolamine hydrochlorideHMDB
Diethanolamine acetateHMDB
Diethanolamine maleate (1:1)HMDB
Diethanolamine phosphateHMDB
Diethanolamine sulfate (2:1)HMDB
Diethanolamine sulfite (1:1)HMDB
Diethanolamine bisulfateMeSH
Diethanolammonium sulfateMeSH
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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-9430000000-79f7d3e25a715793917aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001j-1900000000-bd0861145364bd684950JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0159-5940000000-ebe5523dad23d3dc2391JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9430000000-79f7d3e25a715793917aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-5940000000-ebe5523dad23d3dc2391JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001j-1900000000-bd0861145364bd684950JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05am-9000000000-7eea9eaa21af51853910JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dj-9800000000-3db6474ab842a5d03fb3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4r-9700000000-6ae8b510d6cd7e4ba8d0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0005-9000000000-d0e266aca011203c762aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0005-9000000000-b924f709a47552d0afc1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a4i-0900000000-11bfee15df34ebc320e8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-05g0-9200000000-39da135b20d99fa34636JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00dm-9000000000-74add71de850cb4c8e2dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0005-9000000000-794a61320b2e8c5a8970JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0007-9000000000-af9eeb72884d4847a0a1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0a4i-0900000000-cd466740723ff131d76fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-0900000000-a5ca41984423de95ef78JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-05g0-9200000000-626e5d5103e3012c611eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dm-9000000000-74add71de850cb4c8e2dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0005-9000000000-794a61320b2e8c5a8970JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0007-9000000000-be35c09bcc6cd8c79f05JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-cd466740723ff131d76fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0abi-9500000000-ee4dbde39d4c97f1cae9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2900000000-c1dc229350e5cf19c090JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9500000000-b3018e09980645272c12JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9000000000-ae6bfcca013a433a0a24JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3900000000-d6387d7e1686e32ad49aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-8900000000-66c6a6cce5f90a2cdb52JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-9000000000-7e1da753c608954b27eeJSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-05fr-9000000000-362b201708dabf55f01bJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
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
FoodDB IDFDB023372
KNApSAcK IDNot Available
Chemspider ID13835604
KEGG Compound IDC06772
BioCyc IDCPD-653
BiGG IDNot Available
Wikipedia LinkDiethanolamine
METLIN ID3239
PubChem Compound8113
PDB IDNot Available
ChEBI ID28123
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. 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 ]
  2. 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 ]
  3. Zeisel SH, DaCosta KA, Fox JG: Endogenous formation of dimethylamine. Biochem J. 1985 Dec 1;232(2):403-8. [PubMed:4091797 ]
  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 ]