| Record Information |
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| Version | 2.0 |
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| Created at | 2005-11-16 15:48:42 UTC |
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| Updated at | 2022-01-23 17:12:43 UTC |
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| NP-MRD ID | NP0000818 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Ethanolamine |
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| Description | Ethanolamine (MEA), also known as monoethanolamine, aminoethanol or glycinol, belongs to the class of organic compounds known as 1,2-aminoalcohols (or simply 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 colorless, viscous liquid with an odor reminiscent of ammonia. In pharmaceutical formulations, ethanolamine is used primarily for buffering or preparation of emulsions. Ethanolamine can also be used as pH regulator in cosmetics. Biologically, ethanolamine is an initial precursor for the biosynthesis of two primary phospholipid classes, phosphatidylcholine (PC) and phosphatidylethanolamine (PE). In this regard, ethanolamine is the second-most-abundant head group for phospholipids. Ethanolamine serves as a precursor for a variety of N-acylethanolamines (NAEs). These are molecules that modulate several animal and plant physiological processes such as seed germination, plant–pathogen interactions, chloroplast development and flowering (PMID: 30190434 ). Ethanolamine, when combined with arachidonic acid (C20H32O2; 20:4, ω-6), Can also form the endocannabinoid anandamide. Ethanolamine can be converted to phosphoethanolamine via the enzyme known as ethanolamine kinase. The two substrates of this enzyme are ATP and ethanolamine, whereas its two products are ADP and O-phosphoethanolamine. In most plants ethanolamine is biosynthesized by decarboxylation of serine via a pyridoxal 5'-phosphate-dependent l-serine decarboxylase (SDC). Ethanolamine exists in all living species, ranging from bacteria to plants to humans. Ethanolamine has been detected, but not quantified in, several different foods, such as narrowleaf cattails, mung beans, blackcurrants, white cabbages, and bilberries. |
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| Structure | InChI=1S/C2H7NO/c3-1-2-4/h4H,1-3H2 |
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| Synonyms | | Value | Source |
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| 1-Amino-2-hydroxyethane | ChEBI | | 2-Amino-1-ethanol | ChEBI | | 2-Amino-ethanol | ChEBI | | 2-Aminoethan-1-ol | ChEBI | | 2-Aminoethyl alcohol | ChEBI | | 2-Hydroxyethylamine | ChEBI | | Aethanolamin | ChEBI | | Aminoethanol | ChEBI | | beta-Aminoethanol | ChEBI | | beta-Aminoethyl alcohol | ChEBI | | beta-Ethanolamine | ChEBI | | beta-Hydroxyethylamine | ChEBI | | Colamine | ChEBI | | ETA | ChEBI | | Glycinol | ChEBI | | Hea | ChEBI | | MEA | ChEBI | | MONOETHANOLAMINE | ChEBI | | b-Aminoethanol | Generator | | Β-aminoethanol | Generator | | b-Aminoethyl alcohol | Generator | | Β-aminoethyl alcohol | Generator | | b-Ethanolamine | Generator | | Β-ethanolamine | Generator | | b-Hydroxyethylamine | Generator | | Β-hydroxyethylamine | Generator | | 2-Aminoethanol | HMDB | | 2-Ethanolamine | HMDB | | 2-Hydroxyethanamine | HMDB | | Envision conditioner PDD 9020 | HMDB | | Ethylolamine | HMDB | | H-Glycinol | HMDB | | Monoaethanolamin | HMDB | | Olamine | HMDB | | 2 Aminoethanol | HMDB | | Kolamin | HMDB | | Ethanolamine | PhytoBank |
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| Chemical Formula | C2H7NO |
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| Average Mass | 61.0831 Da |
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| Monoisotopic Mass | 61.05276 Da |
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| IUPAC Name | 2-aminoethan-1-ol |
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| Traditional Name | ethanolamine |
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| CAS Registry Number | 141-43-5 |
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| SMILES | NCCO |
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| InChI Identifier | InChI=1S/C2H7NO/c3-1-2-4/h4H,1-3H2 |
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| InChI Key | HZAXFHJVJLSVMW-UHFFFAOYSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, simulated) | Ahselim | | | 2022-01-23 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, simulated) | v.dorna83@yahoo.com | Not Available | Not Available | 2021-07-29 | View Spectrum |
| | Species |
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| Species of Origin | |
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| Species Where Detected | |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic nitrogen compounds |
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| Class | Organonitrogen compounds |
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| Sub Class | Amines |
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| Direct Parent | 1,2-aminoalcohols |
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| Alternative Parents | |
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| Substituents | - 1,2-aminoalcohol
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Primary amine
- Primary alcohol
- Organooxygen compound
- Primary aliphatic amine
- Alcohol
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Liquid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 10.5 °C | Not Available | | Boiling Point | 170.00 to 172.00 °C. @ 760.00 mm Hg | The Good Scents Company Information System | | Water Solubility | 1000 mg/mL | Not Available | | LogP | -1.31 | Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995). |
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| Predicted Properties | |
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| General References | - 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. [PubMed:12834252 ]
- 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. [PubMed:7895605 ]
- 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. [PubMed:2116174 ]
- 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. [PubMed:8443564 ]
- 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. [PubMed:1504837 ]
- 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. [PubMed:2896652 ]
- Renkonen O: Chromatographic separation of plasmalogenic, alkyl-acyl, and diacyl forms of ethanolamine glycerophosphatides. J Lipid Res. 1968 Jan;9(1):34-9. [PubMed:4295349 ]
- 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. [PubMed:8581486 ]
- 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. [PubMed:10502752 ]
- 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. [PubMed:9130265 ]
- 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. [PubMed:1841636 ]
- Coutinho BG, Mevers E, Schaefer AL, Pelletier DA, Harwood CS, Clardy J, Greenberg EP: A plant-responsive bacterial-signaling system senses an ethanolamine derivative. Proc Natl Acad Sci U S A. 2018 Sep 25;115(39):9785-9790. doi: 10.1073/pnas.1809611115. Epub 2018 Sep 6. [PubMed:30190434 ]
- Kelly RF, Lamont KT, Somers S, Hacking D, Lacerda L, Thomas P, Opie LH, Lecour S: Ethanolamine is a novel STAT-3 dependent cardioprotective agent. Basic Res Cardiol. 2010 Nov;105(6):763-70. doi: 10.1007/s00395-010-0125-0. Epub 2010 Oct 12. [PubMed:20938668 ]
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