1-Aminopropan-2-ol is the

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula CH₃CH(OH)CH2NH₂. It is an

amino alcohol In organic chemistry, alkanolamines are organic compounds that contain both hydroxyl () and amino (, , and ) functional groups on an alkane backbone. The term alkanolamine is a broad class term that is sometimes used as a subclassification. Meth ...

. The term ''isopropanolamine'' may also refer more generally to the additional

homologs A couple of homologous chromosomes, or homologs, are a set of one maternal and one paternal chromosome that pair up with each other inside a cell during fertilization. Homologs have the same genes in the same locus (genetics), loci where they pr ...

diisopropanolamine Diisopropanolamine is a chemical compound with the molecular formula used as an emulsifier, stabilizer, and chemical intermediate. Diisopropanolamine can be prepared by the reaction of isopropanolamine or ammonia with propylene oxide Propylene ...

(DIPA) and

triisopropanolamine Triisopropanolamine is an amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen H ...

(TIPA). 1-Aminopropan-2-ol is

chiral Chirality is a property of asymmetry important in several branches of science. The word ''chirality'' is derived from the Greek (''kheir''), "hand", a familiar chiral object. An object or a system is ''chiral'' if it is distinguishable from ...

. It can be prepared by the addition of aqueous

ammonia Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous was ...

propylene oxide Propylene oxide is an acutely toxic and carcinogenic organic compound with the molecular formula CH3CHCH2O. This colourless volatile liquid with an odour similar to ether, is produced on a large scale industrially. Its major application is its us ...

Biosynthesis

(''R'')-1-Aminopropan-2-ol is one of the components incorporated in the

biosynthesis of cobalamin Cobalamin biosynthesis is the process by which bacteria and archea make cobalamin, vitamin B12. Many steps are involved in converting aminolevulinic acid via uroporphyrinogen III and adenosylcobyric acid to the final forms in which it is used by e ...

. The ''O''-phosphate ester is produced from

threonine Threonine (symbol Thr or T) is an amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH form under biological conditions), a carboxyl group (which is in the deprotonated −COO� ...

by the enzyme

Threonine-phosphate decarboxylase The enzyme threonine-phosphate decarboxylase () catalyzes the chemical reaction : L-threonine O-3-phosphate \rightleftharpoons (R)-1-aminopropan-2-yl phosphate + CO2 This enzyme belongs to the family of lyases, specifically the carboxy-lyases, w ...

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 Cutting fluid is a type of coolant and lubricant designed specifically for metalworking processes, such as machining and stamping. There are various kinds of cutting fluids, which include oils, oil-water emulsions, pastes, gels, aerosols (mists), ...

, waterborne coatings, personal care products, and in the production of

titanium dioxide Titanium dioxide, also known as titanium(IV) oxide or titania , is the inorganic compound with the chemical formula . When used as a pigment, it is called titanium white, Pigment White 6 (PW6), or CI 77891. It is a white solid that is insolubl ...

and

polyurethane Polyurethane (; often abbreviated PUR and PU) refers to a class of polymers composed of organic chemistry, organic units joined by carbamate (urethane) links. In contrast to other common polymers such as polyethylene and polystyrene, polyurethan ...

s. It is an intermediate in the synthesis of a variety of pharmaceutical drugs. (''R'')-1-aminopropan-2-ol is metabolised to

aminoacetone Aminoacetone is the simplest monopeptide with the formula CH3C(O)CH2NH2. Although stable in the gaseous form, once condensed it reacts with itself. The protonated derivative forms stable salts, e.g. aminoacetone hydrochloride ( H3C(O)CH2NH3l)). ...

by the enzyme (''R'')-aminopropanol dehydrogenase. Synthesis of

Hexylcaine Hexylcaine hydrochloride, also called cyclaine (Merck) or osmocaine, is a short-acting local anesthetic. It acts by inhibiting sodium channel conduction. Overdose can lead to headache, tinnitus, numbness and tingling around the mouth and tongue ...

is one application.

References

{{DEFAULTSORT:Amino-2-propanol, 1- Amines Secondary alcohols Amino alcohols