Milk Composition Database: Showing metabocard for Diethanolamine (BMDB0004437)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:09:28 UTC

Update Date

2020-05-11 20:57:17 UTC

MCDB ID

BMDB0004437

Secondary Accession Numbers

BMDB04437

Metabolite Identification

Common Name

Diethanolamine

Description

Diethanolamine, also known as H2DEA or diolamine, 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. Diethanolamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Diethanolamine exists in all living organisms, ranging from bacteria to humans. Diethanolamine is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound.

Structure

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

Synonyms

Value	Source
Bis-(2-hydroxy-ethyl)-amine	ChEBI
Diolamine	ChEBI
H2dEa	ChEBI
N,N-Di(hydroxyethyl)amine	ChEBI
2,2'-Dihydroxydiethylamine	HMDB
2,2'-Iminobis	HMDB
2,2'-Iminobisethanol	HMDB
2,2'-Iminodi-1-ethanol	HMDB
2,2'-Iminodiethanol	HMDB
2,2'Iminobisethanol	HMDB
2-(2-Hydroxyethylamino)ethanol	HMDB
2-[(2-Hydroxyethyl)amino]ethanol	HMDB
Aliphatic amine	HMDB
Bis(2-hydroxyethyl)amine	HMDB
Bis(2-hydroxyethyl)tallow amine oxide	HMDB
Bis(hydroxyethyl)amine	HMDB
Bis-2-hydroxyethylamine	HMDB
DEA	HMDB
Di(2-hydroxyethyl)amine	HMDB
Di(beta-hydroxyethyl)amine	HMDB
Diaethanolamin	HMDB
Diethanolamin	HMDB
Diethylolamine	HMDB
Iminodiethanol	HMDB
N,N'-Iminodiethanol	HMDB
N,N-Bis(2-hydroxyethyl)amine	HMDB
N,N-Diethanolamine	HMDB
Di(β-hydroxyethyl)amine	HMDB
Diethanolamine	HMDB
N,N-Di(2-hydroxyethyl)amine	HMDB

Chemical Formula

C₄H₁₁NO₂

Average Molecular Weight

105.1356

Monoisotopic Molecular Weight

105.078978601

IUPAC Name

2-[(2-hydroxyethyl)amino]ethan-1-ol

Traditional Name

diethanolamine

CAS Registry Number

111-42-2

SMILES

OCCNCCO

InChI Identifier

InChI=1S/C4H11NO2/c6-3-1-5-2-4-7/h5-7H,1-4H2

InChI Key

ZBCBWPMODOFKDW-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.

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

Experimental Properties

Property	Value	Reference
Melting Point	28 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1000 mg/mL at 20 °C	Not Available
LogP	-1.43	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00di-9430000000-79f7d3e25a715793917a	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-001j-1900000000-bd0861145364bd684950	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0159-5940000000-ebe5523dad23d3dc2391	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9430000000-79f7d3e25a715793917a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0159-5940000000-ebe5523dad23d3dc2391	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001j-1900000000-bd0861145364bd684950	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05am-9000000000-7eea9eaa21af51853910	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00dj-9800000000-3db6474ab842a5d03fb3	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4r-9700000000-6ae8b510d6cd7e4ba8d0	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0005-9000000000-d0e266aca011203c762a	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0005-9000000000-b924f709a47552d0afc1	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0a4i-0900000000-11bfee15df34ebc320e8	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-05g0-9200000000-39da135b20d99fa34636	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00dm-9000000000-74add71de850cb4c8e2d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0005-9000000000-794a61320b2e8c5a8970	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0007-9000000000-af9eeb72884d4847a0a1	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0a4i-0900000000-cd466740723ff131d76f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-0900000000-a5ca41984423de95ef78	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-05g0-9200000000-626e5d5103e3012c611e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00dm-9000000000-74add71de850cb4c8e2d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0005-9000000000-794a61320b2e8c5a8970	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0007-9000000000-be35c09bcc6cd8c79f05	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-0900000000-cd466740723ff131d76f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0abi-9500000000-ee4dbde39d4c97f1cae9	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-03k9-9000000000-e03c494989bc56f168ee	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-03di-9000000000-122a3a485bc0a1bfded4	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9000000000-939cd379fb164bb8a094	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-2900000000-c1dc229350e5cf19c090	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-9500000000-b3018e09980645272c12	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9000000000-ae6bfcca013a433a0a24	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-3900000000-d6387d7e1686e32ad49a	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-8900000000-66c6a6cce5f90a2cdb52	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ox-9000000000-7e1da753c608954b27ee	2017-09-01	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-05fr-9000000000-362b201708dabf55f01b	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 28306241	details

External Links

HMDB ID

HMDB0004437

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023372

KNApSAcK ID

Not Available

Chemspider ID

13835604

KEGG Compound ID

C06772

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Diethanolamine

METLIN ID

3239

PubChem Compound

8113

PDB ID

Not Available

ChEBI ID

28123

References

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)

General References

Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]

Showing metabocard for Diethanolamine (BMDB0004437)

Structure for BMDB0004437 (Diethanolamine)