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1-Aminopropan-2-ol
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Isopropanolamine.svg 150px 1-Aminopropan-2-ol 1-Amino-2-propanolIsopropanolamineMIPA; Threamine (R) (S) (+/−)-1-Aminopropan-2-ol (−)-1-Aminopropan-2-ol (+)-1-Aminopropan-2-ol 78-96-6 correct CAS 2799-16-8 correct CAS 2799-17-9 correct CAS 4 439938 7311736 correct chemspider 3 correct chemspider 388968 correct chemspider 5641722 correct kegg C05771 correct EBI 326602 correct EBI 19030 correct chemspider 1S/C3H9NO/c1-3(5)2-4/h3,5H,2,4H2,1H3 correct chemspider HXKKHQJGJAFBHI-UHFFFAOYSA-N 1S/C3H9NO/c1-3(5)2-4/h3,5H,2,4H2,1H3/t3-/m1/s1 HXKKHQJGJAFBHI-GSVOUGTGSA-N 1S/C3H9NO/c1-3(5)2-4/h3,5H,2,4H2,1H3/t3-/m0/s1 HXKKHQJGJAFBHI-VKHMYHEASA-N correct FDA UE40BY1BZW OC(C)CN none O[C@H](C)CN O[C@@H](C)CN 201-162-7 220-532-9 220-533-4 3 9 1 1 liquid ammonia-like 0.973 g/mL (18 °C) Amino-2-propanol at Sigma-Aldrich 1.74 159.46 soluble soluble in alcohol, ether, acetone, benzene, CCl4 1.4479
77 374 2 2 0 4.26 g/kg (rat, oral)
1-Aminopropan-2-ol is the organic compound with the formula CH3CH(OH)CH2NH2. 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.9781119371809 March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure Smith Michael B. 19 February 2020 John Wiley & Sons
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.10.1021/bi012111w Three-Dimensional Structure of the L-Threonine-O-3-phosphate Decarboxylase (CobD) Enzyme from Salmonella enterica 2002 Cheong Cheom-Gil Bauer Cary B. Brushaber Kevin R. Escalante-Semerena Jorge C. Ivan Rayment Rayment Ivan Biochemistry 41 15 4798–4808 11939774 10.1039/b108967f The biosynthesis of adenosylcobalamin (Vitamin B12) 2002 Warren Martin J. Raux Evelyne Schubert Heidi L. Escalante-Semerena Jorge C. Natural Product Reports 19 4 390–412 12195810
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. http://www.hbltrade.com/pid10029823/Monoisopropanolamine.htm Monoisopropanolamine Nanjing HBL International 2020-04-28 2020-11-06 https://web.archive.org/web/20201106223736/http://www.hbltrade.com/pid10029823/Monoisopropanolamine.htm dead It is an intermediate in the synthesis of a variety of pharmaceutical drugs.April 2020
(R)-1-aminopropan-2-ol is metabolised to aminoacetone by the enzyme (R)-aminopropanol dehydrogenase.10.1042/bj1040112 Microbial metabolism of amino ketones. L-1-aminopropan-2-ol dehydrogenase and L-threonine dehydrogenase in Escherichia coli 1967 Turner JM Biochemical Journal 104 1 112–121 5340733 1270551
Synthesis of Hexylcaine is one application.
References
Category:Amines
Category:Secondary alcohols
Category:Amino alcohols
Category:Foul-smelling chemicals