Alkanolamines are chemical compounds that contain both hydroxyl (-OH) and amino (-NH2, -NHR, and -NR2) functional groups on an alkane backbone. The term alkanolamine is a broad class term that is sometimes used as a subclassification.[1]
2-Aminoalcohols
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2-Aminoalcohols are an important class of organic compounds that contain both an amine and an alcohol functional groups. They are generated often by the reaction of amines with epoxides. Such compounds find a variety of industrial applications. Simple alkanolamines are used as solvents, synthetic intermediates, and high-boiling bases.[2]
Common amino alcohols
- Ethanolamines
- Aminomethyl propanol
- Heptaminol
- Isoetarine
- Propanolamines
- Sphingosine
- Methanolamine (simplest amino alcohol)
- Dimethylethanolamine
- N-Methylethanolamine
Beta blockers
A subclass of beta blockers is often called alkanolamine beta blockers. Typical examples are:
Natural products
Most proteins and peptides contain both alcohols and amino groups. Two amino acids are alkanolamines, formally speaking: serine and hydroxyproline.
- Veratridine and veratrine
- Tropane alkaloids such as atropine
- hormones and neurotransmitters epinephrine (adrenaline) and norepinephrine (noradrenaline)
2-Amino alcohols from amino acids
In principle, each amino acid can be hydrogenated to the corresponding 2-aminoalcohol. Examples include prolinol (from proline) and valinol (from valine). Some example for EO ethylene oxide and PO propylene oxide reaction that eventually yield aminoalcohol: C2H4O + R-NH2 --> RNHC2H4OH [3]
C3H6O + R-NH2 --> RNHC3H6OH[4]
See also
References
- ^ Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, ISBN 978-0-471-72091-1
- ^ Matthias Frauenkron; Johann-Peter Melder; Günther Ruider; Roland Rossbacher; Hartmut Höke (2002). "Ethanolamines and Propanolamines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_001. ISBN 3527306730.
- ^ Ethylene oxide
- ^ Propylene oxide
External links
- Amino+Alcohols at the US National Library of Medicine Medical Subject Headings (MeSH)