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1-Aminopropan-2-ol

Isopropanolamine MIPA; Threamine | NFPA-H = 2 | NFPA-F = 2 | NFPA-R = 0

1-Aminopropan-2-ol is the organic compound with the formula . It is an amino alcohol. The term isopropanolamine may also refer more generally to the additional homologs diisopropanolamine (DIPA) and triisopropanolamine (TIPA).

1-Aminopropan-2-ol is chiral. It can be prepared by the addition of aqueous ammonia to propylene oxide.

Biosynthesis

(R)-1-Aminopropan-2-ol is one of the components incorporated in the biosynthesis of cobalamin. The O-phosphate ester is produced from threonine by the enzyme Threonine-phosphate decarboxylase.

Applications

The isopropanolamines are used as buffers. They are good solubilizers of oil and fat, so they are used to neutralize fatty acids and sulfonic acid-based surfactants. Racemic 1-aminopropan-2-ol is typically used in metalworking fluid, waterborne coatings, personal care products, and in the production of titanium dioxide and polyurethanes. It is an intermediate in the synthesis of a variety of pharmaceutical drugs.

(R)-1-aminopropan-2-ol is metabolised to aminoacetone by the enzyme (R)-aminopropanol dehydrogenase.

Synthesis of Hexylcaine is one application.

References

References

  1. [http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/110248 Amino-2-propanol] at Sigma-Aldrich
  2. (19 February 2020). "March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure". John Wiley & Sons.
  3. (2002). "Three-Dimensional Structure of the L-Threonine-''O''-3-phosphate Decarboxylase (CobD) Enzyme from ''Salmonella enterica''". Biochemistry.
  4. (2002). "The biosynthesis of adenosylcobalamin (Vitamin B12)". Natural Product Reports.
  5. "Monoisopropanolamine". Nanjing HBL International.
  6. (1967). "Microbial metabolism of amino ketones. L-1-aminopropan-2-ol dehydrogenase and L-threonine dehydrogenase in ''Escherichia coli''". Biochemical Journal.
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amines secondary-alcohols amino-alcohols
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