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Record Information
Version3.6
Creation Date2006-08-13 18:57:19 UTC
Update Date2013-02-09 00:13:12 UTC
HMDB IDHMDB04437
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.
Structure
Thumb
Synonyms
  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 IUPAC 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
KingdomOrganic Compounds
Super ClassAliphatic Acyclic Compounds
ClassAlkylamines
Sub Class1,2-Aminoalcohols
Other Descriptors
  • Alkylamines
  • ethanolamines(ChEBI)
Substituents
  • Primary Alcohol
Direct Parent1,2-Aminoalcohols
Ontology
StatusDetected and Not Quantified
Origin
  • Cosmetic
  • Drug
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 area52.49ChemAxon
rotatable bond count4ChemAxon
refractivity27.28ChemAxon
polarizability11.63ChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Urine
Tissue Location
  • Thyroid Gland
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
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. 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. 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