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Ethanolamine (CHEM003726)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (4)XML
Record Information
Version1.0
Creation Date2014-09-11 05:15:49 UTC
Update Date2016-10-28 10:02:25 UTC
Accession NumberCHEM003726
Identification
Common NameEthanolamine
ClassSmall Molecule
DescriptionEthanolamine is a viscous, hygroscopic amino alcohol with an ammoniacal odor. It is widely distributed in biological tissue and is a component of lecithin. It is used as a surfactant, fluorometric reagent, and to remove CO2 and H2S from natural gas and other gases.
Contaminant Sources
  • Cosmetic Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Animal Toxin
  • Food Toxin
  • Household Toxin
  • Indicator and Reagent
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass61.083 g/mol
Monoisotopic Mass61.053 g/mol
CAS Registry Number141-43-5
IUPAC Name2-aminoethan-1-ol
Traditional Nameethanolamine
SMILESNCCO
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue Locations
  • Brain
  • Epidermis
  • Most Tissues
  • Myelin
  • Nerve Cells
  • Pancreas
  • Stratum Corneum
Pathways
NameSMPDB LinkKEGG Link
Phospholipid BiosynthesisSMP00025 map00564
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point10.5°C
Boiling Point171°C
Solubility1000.0 mg/mL
Predicted Properties
PropertyValueSource
Water Solubility849 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-1900000000-b64e859a0bfc46cdfcbfView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-1900000000-384c99d021f0303a9d78View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00di-1900000000-d731dd07c2dfa0287f5fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-8900000000-ec4268b6041043d15437View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-2900000000-02697b8ce238020537aaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-001i-9000000000-e06e8502ffb0d4113432View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-001i-9000000000-7160c3fea0c0159e447aView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-001i-9000000000-2af16a98e43fadfa86a3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-1900000000-b64e859a0bfc46cdfcbfView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-1900000000-384c99d021f0303a9d78View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-1900000000-d731dd07c2dfa0287f5fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-8900000000-ec4268b6041043d15437View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00di-2900000000-02697b8ce238020537aaView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0fki-2900000000-37831b0ceb554ca4edd2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS)splash10-001i-9100000000-e2cbdef448451ceae424View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03dl-9000000000-17dee0c07bf5cddb79ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-9000000000-04f4c1792f8ab4f4646fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03di-9000000000-761836be8f1018081210View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-001i-9000000000-7160c3fea0c0159e447aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positivesplash10-001i-9000000000-2af16a98e43fadfa86a3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-03di-9000000000-ae5b80bd3c5c11914ea6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0006-9000000000-6abb3d0944e188778c65View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0007-9000000000-e477e52f411d933a30b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-d7979261a3716365d5aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-03di-9000000000-5c0261b2dcc6ae1291a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-9000000000-ae5b80bd3c5c11914ea6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-6abb3d0944e188778c65View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0007-9000000000-e477e52f411d933a30b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-d7979261a3716365d5aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-9000000000-5c0261b2dcc6ae1291a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-9e6d219a7fbd8624cd6bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-9000000000-fb9020ee9b301ec7766fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-a4ae359cfcc0245b4d19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9000000000-b6ed81bc049b8d3042f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-9000000000-78c77096ed599182b5bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-f199cbf8312e0b466f1bView in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-b8e7ed9f5ad724511431View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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 Reference

John W. Varwig, “Method of making the ethanolamine salt of N-nitrosophenylhydroxylamine.” U.S. Patent US4898976, issued February, 1969.

MSDSLink
General References
1. Soucaille, Philippe. Ethanolamine production by fermentation of genetically modified Escherichia coli. PCT Int. Appl. (2007), 23pp.
2. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.
3. 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.
4. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.
5. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.
6. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)
7. Soucaille, Philippe. Ethanolamine production by fermentation of genetically modified Escherichia coli. PCT Int. Appl. (2007), 23pp.
8. Denissen JF, Grabowski BA, Johnson MK, Boyd SA, Uchic JT, Stein H, Cepa S, Hill P: The orally active renin inhibitor A-74273. In vivo and in vitro morpholine ring metabolism in rats, dogs, and humans. Drug Metab Dispos. 1994 Nov-Dec;22(6):880-8.
9. Vance JE: Lipoproteins secreted by cultured rat hepatocytes contain the antioxidant 1-alk-1-enyl-2-acylglycerophosphoethanolamine. Biochim Biophys Acta. 1990 Jul 16;1045(2):128-34.
10. Alberghina M, Giacchetto A, Cavallaro N: Levels of ethanolamine intermediates in the human and rat visual system structures: comparison with neural tissues of a lower vertebrate (Mustelus canis) and an invertebrate (Loligo pealei). Neurochem Int. 1993 Jan;22(1):45-51.
11. Hammond EJ, Uthman BM, Wilder BJ, Ben-Menachem E, Hamberger A, Hedner T, Ekman R: Neurochemical effects of vagus nerve stimulation in humans. Brain Res. 1992 Jun 26;583(1-2):300-3.
12. Perschak H, Amsler U, Vischer A, Siegfried J, Cuenod M: Ventricular cerebrospinal fluid concentrations of putative amino acid transmitters in Parkinson's disease and other disorders. Hum Neurobiol. 1987;6(3):191-4.
13. Renkonen O: Chromatographic separation of plasmalogenic, alkyl-acyl, and diacyl forms of ethanolamine glycerophosphatides. J Lipid Res. 1968 Jan;9(1):34-9.
14. Ginsberg L, Rafique S, Xuereb JH, Rapoport SI, Gershfeld NL: Disease and anatomic specificity of ethanolamine plasmalogen deficiency in Alzheimer's disease brain. Brain Res. 1995 Nov 6;698(1-2):223-6.
15. Bluml S, Seymour KJ, Ross BD: Developmental changes in choline- and ethanolamine-containing compounds measured with proton-decoupled (31)P MRS in in vivo human brain. Magn Reson Med. 1999 Oct;42(4):643-54.
16. Farooqui AA, Rapoport SI, Horrocks LA: Membrane phospholipid alterations in Alzheimer's disease: deficiency of ethanolamine plasmalogens. Neurochem Res. 1997 Apr;22(4):523-7.
17. Mikhaevich IS, Vlasenkova NK, Gerasimova GK: Synergistic antiproliferative effect of cis-diammine-dichloroplatinum (II) and a new anticancer agent, plasmanyl-(N-acyl)-ethanolamine, an inhibitor of protein kinase C. Biomed Sci. 1991;2(6):659-64.
18. Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50.
19. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3.
20. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=10930630
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=12834252
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=15149650
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=24023812
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=3654008
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=6196640
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=6708049