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Record Information
Version	2.0
Creation Date	2012-08-03 14:57:55 -0600
Update Date	2015-09-13 15:15:32 -0600
Secondary Accession Numbers	ECMDB21405
Identification
Name:	Diethanolamine
Description	Diethanolamine, 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	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xabfa4ba4> Close
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.
Kingdom	Organic compounds
Super Class	Organic nitrogen compounds
Class	Organonitrogen compounds
Sub Class	Amines
Direct Parent	1,2-aminoalcohols
Alternative Parents	Dialkylamines Primary alcohols Organopnictogen compounds Hydrocarbon derivatives
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 Framework	Aliphatic acyclic compounds
External Descriptors	ethanolamines (CHEBI:28123 )
Physical Properties
State:	Solid
Charge:	1
Melting point:	28 °C
Experimental Properties:	Property Value Source Water Solubility: 1000 mg/mL at 20 oC [DOW CHEMICAL COMPANY (1980)] PhysProp LogP: -1.43 [HANSCH,C ET AL. (1995)] PhysProp
Predicted Properties	Property Value Source Water Solubility 466 g/L ALOGPS logP -1.4 ALOGPS logP -1.6 ChemAxon logS 0.65 ALOGPS pKa (Strongest Acidic) 15.3 ChemAxon pKa (Strongest Basic) 9.26 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 52.49 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 27.28 m³·mol⁻¹ ChemAxon Polarizability 11.63 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Concentration Strain Media Growth Status Growth System Temperature Details 20± 0 uM BW25113 48 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 Gluco Stationary Phase, glucose limited Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 37 oC PMID: 17379776 Find out more about how we convert literature concentrations.
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) splash10-00di-9430000000-79f7d3e25a715793917a View in MoNA GC-MS GC-MS Spectrum - GC-MS (2 TMS) splash10-001j-1900000000-bd0861145364bd684950 View in MoNA GC-MS GC-MS Spectrum - GC-MS (3 TMS) splash10-0159-5940000000-ebe5523dad23d3dc2391 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-00di-9430000000-79f7d3e25a715793917a View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-0159-5940000000-ebe5523dad23d3dc2391 View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-001j-1900000000-bd0861145364bd684950 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-05am-9000000000-7eea9eaa21af51853910 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-00dj-9800000000-3db6474ab842a5d03fb3 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-0a4r-9700000000-6ae8b510d6cd7e4ba8d0 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-0005-9000000000-d0e266aca011203c762a View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) splash10-0005-9000000000-b924f709a47552d0afc1 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive splash10-0a4i-0900000000-11bfee15df34ebc320e8 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive splash10-05g0-9200000000-39da135b20d99fa34636 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive splash10-00dm-9000000000-74add71de850cb4c8e2d View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive splash10-0005-9000000000-794a61320b2e8c5a8970 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive splash10-0007-9000000000-af9eeb72884d4847a0a1 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive splash10-0a4i-0900000000-cd466740723ff131d76f View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-0a4i-0900000000-a5ca41984423de95ef78 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-05g0-9200000000-626e5d5103e3012c611e View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-00dm-9000000000-74add71de850cb4c8e2d View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-0005-9000000000-794a61320b2e8c5a8970 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-0007-9000000000-be35c09bcc6cd8c79f05 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , positive splash10-0a4i-0900000000-cd466740723ff131d76f View in MoNA LC-MS/MS LC-MS/MS Spectrum - , positive splash10-0abi-9500000000-ee4dbde39d4c97f1cae9 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Negative splash10-03k9-9000000000-e03c494989bc56f168ee View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Negative splash10-03di-9000000000-122a3a485bc0a1bfded4 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Positive splash10-0007-9000000000-939cd379fb164bb8a094 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0a4i-2900000000-c1dc229350e5cf19c090 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0a4r-9500000000-b3018e09980645272c12 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0007-9000000000-ae6bfcca013a433a0a24 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0udi-3900000000-d6387d7e1686e32ad49a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0udi-8900000000-66c6a6cce5f90a2cdb52 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-01ox-9000000000-7e1da753c608954b27ee View in MoNA MS Mass Spectrum (Electron Ionization) splash10-05fr-9000000000-362b201708dabf55f01b View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View 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)
Links
External Links:	Resource Link CHEBI ID 28123 HMDB ID HMDB04437 Pubchem Compound ID 8113 Kegg ID C06772 ChemSpider ID 13835604 Wikipedia Diethanolamine BioCyc ID Not Available