This is a secondary amino acid, which is formed in vivo by the degradation of dihydrouracil and carnosine. Because neuronal uptake and neuronal receptor sensitivity to β-alanine have been demonstrated, the compound may be a false transmitter replacing GABA. A rare genetic disorder, hyper-β-alaninemia, has been reported. It is used as a flavor enhancer, flavoring agent, nutrient supplement or adjuvant. β-Alanine has a slightly sweet taste.
ChEBI: A naturally-occurring beta-amino acid comprising propionic acid with the amino group in the 3-position.
It is widely used in medicine, feed, food, and other industries, mostly to synthesize pantothenic acid and calcium pantothenate (a medicine and feed additive), carnosine, pamidronate sodium, barley nitrogen. It is also used to produce plating corrosion inhibiter, as a biological reagent, and as an organic synthesis intermediate. Used as a food and health supplement additive. Endogenous beta-amino acids, non-selective glycine receptor agonists ，G-protein-coupled orphan receptor (TGR7, MrgD) ligand. Relying on the stability of marine biology, beta-aminopropionic acid has a protective effect on cells.
β-Alanine is a naturally occurring beta amino acid. β-Alanine is formed in vivo by the degradation of dihydrouracil (D449990) and carnosine. β-Alanine is also the rate-limiting precursor of carnosine,
as a result supplementation with β-alanine increases the concentration of carnosine in muscles.
White crystalline powder
- Acrylonitrile and ammonia react in a solution of diphenylamine and t-butanol to create beta-aminopropionitrile, which is then alkalized to obtain beta-aminopropionic acid. In a dry autoclave, sequentially add acrylonitrile, diphenylamine and t- butanol, and stir for 5min. Then, add liquid ammonia, maintain the temperature at 100-109℃ and pressure at 1MPa, and stir for 4h. Cool to below 10℃ and stop mixing when the pressure reaches atmospheric pressure. At 65-70℃/(8.0-14.7kPa), decrease the pressure to recover t-butanol to obtain crude beta-aminopropionitrile. Distill the crude product under low pressure, collect the 66-105℃/（1.33-4.0kPa） distillation to obtain beta-aminopropionitrile, and maintain temperature for 1h. Steam under low pressure for half an hour to remove the ammonia in the reaction solution, add water, and drop in hydrochloric until PH reaches 7-7.2. Filter to remove trace impurities. Concentrate the filtered liquid until a large amount of solid precipitates, extract while hot and cool to below 10℃. Filter and vacuum dry to obtain beta-aminopropionic acid. This method requires 982kg beta-aminopropionitrile for every ton of product, and the yield of alkalization is 90%.
- Place the alkaline sodium hypochlorite solution obtained from degradation of succinimide (Hoc reaction) (containing 14% sodium hypochlorite, 8% sodium hydroxide, 30% sodium carbonate) and ice into a reaction chamber, mix and add succinimide, and let react at 18-25℃ for 0.5h. Increase temperature to 40-50℃ and allow to react for 1h. Add hydrochloric acid to adjust the PH to 4-5, decrease the pressure to condense. After condensed and cooled, add 3 times the amount of 95% ethanol to allow inorganic salts to precipitate, filter, and repeat once again. Then, dilute the filtered liquid with 4 times the amount of distilled water and reflux for 1h. Add activated charcoal to remove color, filter, and pass the filtered liquid through exchange resin. Add activated charcoal to remove color, filter, decrease pressure to condense, cool to crystalize, filter, use distilled water to recrystallize once, and obtain beta-aminopropionic acid.
- Hydrolyze and acidify beta-aminopropionitrile to obtain.
Crystallise β-alanine by dissolving it in a hot saturated aqueous solution, filtering, adding four volumes of absolute EtOH and cooling in an ice-bath. Recrystallise it in the same way and then finally, crystallise it from a warm saturated solution in 50% EtOH and adding four volumes of absolute EtOH with cooling in an ice-bath. The crystals are dried in a vacuum desiccator over P2O5. [Donovan & Kegeles J Am Chem Soc 83 255 1961, Beilstein 4 IV 2526.]