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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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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

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:

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 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	27.28 m³·mol⁻¹	ChemAxon
Polarizability	11.63 Å³	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

Show entries

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

Showing 1 to 1 of 1 entries

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

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Diethanolamine (M2MDB001800)

Structure for #<Compound:0xb2c21764>