Description
3-Amino-1,2-propanediol (APD) is a calcium metabolism regulator useful in the treatment of Paget's disease, tumor-induced hypercalcemia and other bone disorders involving increased osteoclastic activity.
Chemical Properties
3-Amino-1,2-propanediol is a very viscous transparent colorless to pale yellow liquid with a melting point of 55-57 °C and a boiling point of 264-265 °C. The density at 25 °C is 1.175 g/mL. soluble in water.
Originator
Henkel (W. Germany)
Uses
3-Amino-1,2-propanediol is used in the preparation of iohexol, which is a X-CT non-ionic contrast medium. It acts as a starting material in the production of specialty materials.
Application
3-Amino-1,2-propanediol is used as a reactant in the synthesis of lipid-like delivery molecules(lipidoids) for RNA interference (RNAi) therapeutics. It is also used in the synthesis of the bioactive template to prepare cationic α-helical polypeptides and various cationic polymers for gene delivery. It is also used in the synthesis of Decarbazolyl Carvedilol (D212720), a metabolite of Carvedilol (C184625) found in humans, rats, dogs and mice.
Preparation
3-Amino-1,2-propanediol is synthesized by reacting 3-chloro-1,2-propanediol (CPD) with ammonia in alkaline environment by adding sodium hydroxide. Afterwards, the product undergoes a series of purification steps.
Application
3-Amino-1,2-propanediol is used as a chiral selector ligand, used subsequently for a nucleophilic substitution with the dimethoxytrityl (DMT)-protected.
General Description
3-Amino-1,2-propanediol is a chiral glycerol derivative. It could used as a hydrogen bond donor in the design of a new deep eutectic solvent which have emerged as a suitable alternative to VOCs (volatile organic compounds) for diverse practical applications including, among others, drug delivery, electrochemistry, material design, extractions and, of course, organic reactions, alone or together twith other sustainable reaction-media[1]. It can also used as a core present in antiviral compounds to skeleton to design a novel class of anti-adenovirus agents[2].
Hazard
3-Amino-1,2-propanediol is Danger.
H314 (93.33%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
H318 (56.36%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
Safety Profile
Poison by intraperitoneal route.Moderately toxic by ingestion. When heated todecomposition it emits toxic fumes of NOx.
storage
3-Amino-1,2-propanediol absorbs moisture and needs to be kept in a container sealed. Store in cool, dry conditions in well-sealed containers.
References
[1] Antenucci A, et al. Design of a New Chiral Deep Eutectic Solvent Based on 3-Amino-1,2-propanediol and Its Application in Organolithium Chemistry. Molecules, 2022; 27.
[2] Mazzotta S, et al. Design, synthesis and in vitro biological evaluation of a novel class of anti-adenovirus agents based on 3-amino-1,2-propanediol. Bioorganic Chemistry, 2021; 114: 105095.
