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Record Information
Creation Date2006-08-13 18:57:19 UTC
Update Date2016-02-11 01:06:44 UTC
Secondary Accession Numbers
  • HMDB03091
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.
  1. 2,2'-Dihydroxydiethylamine
  2. 2,2'-Iminobis
  3. 2,2'-Iminobisethanol
  4. 2,2'-Iminodi-1-ethanol
  5. 2,2'-Iminodiethanol
  6. 2,2'Iminobisethanol
  7. 2-(2-Hydroxyethylamino)ethanol
  8. 2-[(2-Hydroxyethyl)amino]ethanol
  9. Aliphatic amine
  10. Bis(2-hydroxyethyl)amine
  11. Bis(2-hydroxyethyl)tallow amine oxide
  12. Bis(hydroxyethyl)amine
  13. Bis-2-hydroxyethylamine
  14. DEA
  15. Di(2-hydroxyethyl)amine
  16. Di(beta-hydroxyethyl)amine
  17. Diaethanolamin
  18. Diethanolamin
  19. Diethanolamine
  20. Diethylolamine
  21. Dihydroxyethyl tallowamine oxide
  22. Diolamine
  23. H2dea
  24. Iminodiethanol
  25. N,N'-Iminodiethanol
  26. N,N-Bis(2-hydroxyethyl)amine
  27. N,N-Di(hydroxyethyl)amine
  28. N,N-Diethanolamine
  29. Niax DEOA-LF
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
InChI Identifier
Chemical Taxonomy
DescriptionThis compound 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 ClassOrganonitrogen compounds
Sub ClassAlkanolamines
Direct Parent1,2-aminoalcohols
Alternative Parents
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
StatusDetected but not Quantified
  • Cosmetic
  • Drug
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
Experimental Properties
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
Water Solubility466.0 mg/mLALOGPS
pKa (Strongest Acidic)15.3ChemAxon
pKa (Strongest Basic)9.26ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area52.49 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity27.28 m3·mol-1ChemAxon
Polarizability11.63 Å3ChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-zgd0000000-79f7d3e25a715793917aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-6z00000000-bd0861145364bd684950View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-kzi0000000-ebe5523dad23d3dc2391View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-zt00000000-6ae8b510d6cd7e4ba8d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-z100000000-d0e266aca011203c762aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-z200000000-b924f709a47552d0afc1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-2z00000000-11bfee15df34ebc320e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-zb00000000-39da135b20d99fa34636View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-z000000000-74add71de850cb4c8e2dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-z000000000-794a61320b2e8c5a8970View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-z000000000-af9eeb72884d4847a0a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0z00000000-cd466740723ff131d76fView in MoNA
MSMass Spectrum (Electron Ionization)splash10-z000000000-362b201708dabf55f01bView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Urine
Tissue Location
  • Thyroid Gland
PathwaysNot Available
Normal Concentrations
UrineDetected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023372
KNApSAcK IDNot Available
Chemspider ID13835604
KEGG Compound IDC06772
BioCyc IDCPD-653
BiGG IDNot Available
Wikipedia LinkDiethanolamine
NuGOwiki LinkHMDB04437
Metagene LinkHMDB04437
PubChem Compound8113
PDB IDNot Available
ChEBI ID28123
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. 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. [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. [8818565 ]
  3. Zeisel SH, DaCosta KA, Fox JG: Endogenous formation of dimethylamine. Biochem J. 1985 Dec 1;232(2):403-8. [4091797 ]
  4. 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. [12571685 ]