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Record Information
Version1.0
Creation Date2016-07-13 19:41:35 UTC
Update Date2016-07-20 20:49:28 UTC
LmdbLMDB00064
Secondary Accession NumbersNone
Metabolite Identification
Common NameEthanolamine
DescriptionEthanolamine, also known as aminoethanol or glycinol, 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. Ethanolamine is a very strong basic compound (based on its pKa). Ethanolamine exists in all living species, ranging from bacteria to humans. Outside of the human body, Ethanolamine is found, on average, in the highest concentration within milk (cow) and beers. Ethanolamine has also been detected, but not quantified in, several different foods, such as narrowleaf cattails, mung beans, blackcurrants, white cabbages, and bilberries. This could make ethanolamine a potential biomarker for the consumption of these foods. Ethanolamine is biosynthesized by decarboxylation of serine:HOCH2CH(CO2H)NH2 → HOCH2CH2NH2 + CO2Ethanolamine is the second-most-abundant head group for phospholipids, substances found in biological membranes (particularly those of prokaryotes); e.g., phosphatidylethanolamine. Ethanolamine is a potentially toxic compound. Ethanolamine, with regard to humans, has been found to be associated with several diseases such as colorectal cancer, ulcerative colitis, and ethanolaminuria; ethanolamine has also been linked to several inborn metabolic disorders including maple syrup urine disease and propionic acidemia. A class of antihistamines is identified as ethanolamines, which includes carbinoxamine, clemastine, dimenhydrinate, Chlorphenoxamine, diphenhydramine and doxylamine. MEA scrubbing solutions can be recycled through a regeneration unit. It is also an injectable sclerosant as a treatment option of symptomatic hemorrhoids.
Structure
Thumb
Synonyms
ValueSource
1-Amino-2-hydroxyethaneChEBI
2-Amino-1-ethanolChEBI
2-Amino-ethanolChEBI
2-Aminoethan-1-olChEBI
2-Aminoethyl alcoholChEBI
2-HydroxyethylamineChEBI
AethanolaminChEBI
AminoethanolChEBI
beta-AminoethanolChEBI
beta-Aminoethyl alcoholChEBI
beta-EthanolamineChEBI
beta-HydroxyethylamineChEBI
ColamineChEBI
ETAChEBI
GlycinolChEBI
HeaChEBI
MEAChEBI
MONOETHANOLAMINEChEBI
b-AminoethanolGenerator
Β-aminoethanolGenerator
b-Aminoethyl alcoholGenerator
Β-aminoethyl alcoholGenerator
b-EthanolamineGenerator
Β-ethanolamineGenerator
b-HydroxyethylamineGenerator
Β-hydroxyethylamineGenerator
2-AminoethanolHMDB
2-EthanolamineHMDB
2-HydroxyethanamineHMDB
Envision conditioner PDD 9020HMDB
EthylolamineHMDB
H-GlycinolHMDB
MonoaethanolaminHMDB
OlamineHMDB
2 AminoethanolHMDB
EthanolaminePhytoBank
KolaminPhytoBank
Chemical FormulaC2H7NO
Average Molecular Weight61.0831
Monoisotopic Molecular Weight61.052763851
IUPAC Name2-aminoethan-1-ol
Traditional Nameethanolamine
CAS Registry Number141-43-5
SMILES
NCCO
InChI Identifier
InChI=1S/C2H7NO/c3-1-2-4/h4H,1-3H2
InChI KeyHZAXFHJVJLSVMW-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.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct Parent1,2-aminoalcohols
Alternative Parents
Substituents
  • 1,2-aminoalcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Primary aliphatic amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.5ALOGPS
logP-1.3ChemAxon
logS1.14ALOGPS
pKa (Strongest Acidic)15.61ChemAxon
pKa (Strongest Basic)9.55ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity16.21 m³·mol⁻¹ChemAxon
Polarizability6.63 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-1900000000-b64e859a0bfc46cdfcbfSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-1900000000-384c99d021f0303a9d78Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00di-1900000000-d731dd07c2dfa0287f5fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-8900000000-ec4268b6041043d15437Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-2900000000-02697b8ce238020537aaSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-7160c3fea0c0159e447aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-2af16a98e43fadfa86a3Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-b64e859a0bfc46cdfcbfSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-384c99d021f0303a9d78Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-d731dd07c2dfa0287f5fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-8900000000-ec4268b6041043d15437Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-2900000000-02697b8ce238020537aaSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fki-2900000000-37831b0ceb554ca4edd2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-e06e8502ffb0d4113432Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-001i-9100000000-e2cbdef448451ceae424Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03dl-9000000000-17dee0c07bf5cddb79ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-9000000000-04f4c1792f8ab4f4646fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03di-9000000000-761836be8f1018081210Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-001i-9000000000-7160c3fea0c0159e447aSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positivesplash10-001i-9000000000-2af16a98e43fadfa86a3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-03di-9000000000-ae5b80bd3c5c11914ea6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0006-9000000000-6abb3d0944e188778c65Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0007-9000000000-e477e52f411d933a30b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-d7979261a3716365d5aeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-03di-9000000000-5c0261b2dcc6ae1291a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-9000000000-ae5b80bd3c5c11914ea6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-6abb3d0944e188778c65Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0007-9000000000-e477e52f411d933a30b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-d7979261a3716365d5aeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-9000000000-5c0261b2dcc6ae1291a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-03di-9000000000-f09b61222ca342d2835cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-3f9346b7fb6fdd5c5ce8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-03di-9000000000-f73d8d00f0f234521971Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-eec6f92ad146ef43c111Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-9e6d219a7fbd8624cd6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-9000000000-fb9020ee9b301ec7766fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-a4ae359cfcc0245b4d19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9000000000-b6ed81bc049b8d3042f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-9000000000-78c77096ed599182b5bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-f199cbf8312e0b466f1bSpectrum
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-b8e7ed9f5ad724511431Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Kidney
  • Liver
  • Lung
  • Milk
  • Plasma
  • Ruminal Fluid
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Cerebrospinal Fluid (CSF)Detected but not QuantifiedNot ApplicableNot AvailableOvine details
Cerebrospinal Fluid (CSF)Detected but not QuantifiedNot ApplicableNot AvailableOvine details
FecesDetected but not QuantifiedNot ApplicableNot AvailableOvine details
FecesDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
KidneyDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
LiverDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
LungDetected and Quantified0.11+/-0.01 umol/gNot AvailablePorcine details
MilkDetected and Quantified323 uMNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
Ruminal FluidDetected and Quantified73.8 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified85.9 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified134 +/- 55 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified152.3 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified152 +/- 55 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified183.9 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified73 +/- 15 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified86 +/- 33 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified86 +/- 33 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Fozia Saleem, Sou...
details
UrineDetected but not QuantifiedNot ApplicableNot AvailableBovine details
UrineDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDDB03994
HMDB IDHMDB0000149
FooDB IDFDB030851
Phenol Explorer IDNot Available
KNApSAcK IDC00007279
BiGG ID34189
BioCyc IDETHANOL-AMINE
METLIN ID3207
PDB IDNot Available
Wikipedia LinkEthanolamine
Chemspider ID13835336
ChEBI ID16000
PubChem Compound ID700
Kegg Compound IDC00189
YMDB IDYMDB00009
ECMDB IDECMDB00149
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available