1-Aminopropan-2-ol
{{chembox
| ImageFile =Isopropanolamine.svg
| ImageSize =150px
| PIN =1-Aminopropan-2-ol
| OtherNames =1-Amino-2-propanol
Isopropanolamine
MIPA; Threamine
|Section1={{Chembox Identifiers
| index_label =
| index1_label = (R)
| index2_label = (S)
| index_comment = (+/−)-1-Aminopropan-2-ol
| index1_comment = (−)-1-Aminopropan-2-ol
| index2_comment = (+)-1-Aminopropan-2-ol
| CASNo = 78-96-6
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo1 = 2799-16-8
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo2 = 2799-17-9
| CASNo2_Ref = {{cascite|correct|CAS}}
| PubChem = 4
| PubChem1 = 439938
| PubChem2 = 7311736
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3
| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID1 = 388968
| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID2 = 5641722
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C05771
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 326602
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 19030
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C3H9NO/c1-3(5)2-4/h3,5H,2,4H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HXKKHQJGJAFBHI-UHFFFAOYSA-N
| InChI1 = 1S/C3H9NO/c1-3(5)2-4/h3,5H,2,4H2,1H3/t3-/m1/s1
| InChIKey1 = HXKKHQJGJAFBHI-GSVOUGTGSA-N
| InChI2 = 1S/C3H9NO/c1-3(5)2-4/h3,5H,2,4H2,1H3/t3-/m0/s1
| InChIKey2 = HXKKHQJGJAFBHI-VKHMYHEASA-N
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = UE40BY1BZW
| SMILES = OC(C)CN
| Jmol = none
| SMILES1 = O[C@H](C)CN
| SMILES2 = O[C@@H](C)CN
| EC_number = 201-162-7
| EC_number1 = 220-532-9
| EC_number2 = 220-533-4
}}
|Section2={{Chembox Properties
| C=3 | H=9 | N=1 | O=1
| Appearance = liquid
| Odor = ammonia-like
| Density = 0.973 g/mL (18 °C) [http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/110248 Amino-2-propanol] at Sigma-Aldrich
| MeltingPtC =1.74
| MeltingPt_notes =
| BoilingPtC =159.46
| BoilingPt_notes =
| Solubility = soluble
| SolubleOther = soluble in alcohol, ether, acetone, benzene, carbon tetrachloride
| RefractIndex = 1.4479
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPtC = 77
| AutoignitionPtC = 374
| NFPA-H = 2 | NFPA-F = 2 | NFPA-R = 0
| LD50 = 4.26 g/kg (rat, oral)
}}
}}
1-Aminopropan-2-ol is the organic compound with the formula {{chem2|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.{{cite book |isbn=9781119371809 |title=March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure |last1=Smith |first1=Michael B. |date=19 February 2020 |publisher=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.{{cite journal |doi=10.1021/bi012111w |title=Three-Dimensional Structure of the L-Threonine-O-3-phosphate Decarboxylase (CobD) Enzyme from Salmonella enterica |year=2002 |last1=Cheong |first1=Cheom-Gil |last2=Bauer |first2=Cary B. |last3=Brushaber |first3=Kevin R. |last4=Escalante-Semerena |first4=Jorge C. |author5-link=Ivan Rayment |last5=Rayment |first5=Ivan |journal=Biochemistry |volume=41 |issue=15 |pages=4798–4808 |pmid=11939774 }}{{cite journal |doi=10.1039/b108967f |title=The biosynthesis of adenosylcobalamin (Vitamin B12) |year=2002 |last1=Warren |first1=Martin J. |last2=Raux |first2=Evelyne |last3=Schubert |first3=Heidi L. |last4=Escalante-Semerena |first4=Jorge C. |journal=Natural Product Reports |volume=19 |issue=4 |pages=390–412 |pmid=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.{{cite web |url = http://www.hbltrade.com/pid10029823/Monoisopropanolamine.htm |title = Monoisopropanolamine |publisher = Nanjing HBL International |access-date = 2020-04-28}} It is an intermediate in the synthesis of a variety of pharmaceutical drugs.{{Citation needed|date=April 2020}}
(R)-1-aminopropan-2-ol is metabolised to aminoacetone by the enzyme (R)-aminopropanol dehydrogenase.{{cite journal |doi=10.1042/bj1040112 |title=Microbial metabolism of amino ketones. L-1-aminopropan-2-ol dehydrogenase and L-threonine dehydrogenase in Escherichia coli |year=1967 |last1=Turner |first1=JM |journal=Biochemical Journal |volume=104 |issue=1 |pages=112–121 |pmid=5340733 |pmc=1270551 }}
Synthesis of Hexylcaine is one application.
References
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{{DEFAULTSORT:Amino-2-propanol, 1-}}