Alkanolamine

In organic chemistry, alkanolamines (amino alcohols) are organic compounds that contain both hydroxyl (−OH) and amino (−NH2, −NHR, and −NR2) functional groups on an alkane backbone. Alkanolamine's bifunctionality and physicochemical characteristics lead to its use in many applications, such as textiles, cosmetics, agricultural chemical intermediates, drugs, and metal working fluids.[1][2] Many aminoalcohols derivatives also have chemotherapeutic properties. [3]

  • Alkanolamines
  • Methanolamine, from the reaction of ammonia with formaldehyde
  • Ethanolamine
  • 2-Amino-2-methyl-1-propanol is a precursor to oxazolines
  • Valinol is derived from the amino acid valine
  • Sphingosine is a component of some cell membranes.

Alkanolamines usually have high-solubility in water due to the hydrogen bonding ability of both the hydroxyl group and the amino group.[4] Alkanoamines have also shown a broad toxicity for a variety of organisms, including parasites, insect larvae and eggs, and microbes. Studies have also shown that the antimicrobial effect of alkanolamines increases in higher pH's. [5] Most alkanolamines are colorless.[6]

  1. ^ Davis, John W.; Carpenter, Constance L. (1997), Ware, George W. (ed.), "Environmental Assessment of the Alkanolamines", Reviews of Environmental Contamination and Toxicology, 149, New York, NY: Springer New York: 87–137, doi:10.1007/978-1-4612-2272-9_2, ISBN 978-1-4612-7482-7, PMID 8956559, retrieved 2025-03-19
  2. ^ Laskar, Ranjini; Dutta, Subhabrata; Spies, Jan C.; Mukherjee, Poulami; Rentería-Gómez, Ángel; Thielemann, Rebecca E.; Daniliuc, Constantin G.; Gutierrez, Osvaldo; Glorius, Frank (2024-04-17). "γ-Amino Alcohols via Energy Transfer Enabled Brook Rearrangement". Journal of the American Chemical Society. 146 (15): 10899–10907. Bibcode:2024JAChS.14610899L. doi:10.1021/jacs.4c01667. ISSN 0002-7863. PMC 11027157. PMID 38569596.
  3. ^ Ager, David J.; Prakash, Indra; Schaad, David R. (1996-01-01). "1,2-Amino Alcohols and Their Heterocyclic Derivatives as Chiral Auxiliaries in Asymmetric Synthesis". Chemical Reviews. 96 (2): 835–876. doi:10.1021/cr9500038. ISSN 0009-2665.
  4. ^ "Amino Alcohols - Alfa Chemistry". www.alfa-chemistry.com. Retrieved 2025-03-28.
  5. ^ Sandin, M; Allenmark, S; Edebo, L (March 1990). "Selective toxicity of alkanolamines". Antimicrobial Agents and Chemotherapy. 34 (3): 491–493. doi:10.1128/AAC.34.3.491. ISSN 0066-4804. PMC 171625. PMID 2334165.
  6. ^ Cite error: The named reference Ullmann was invoked but never defined (see the help page).
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