Basic information Chemical Properties Description Uses Preparation Safety Related Supplier
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beta-Alanine

Basic information Chemical Properties Description Uses Preparation Safety Related Supplier
beta-Alanine Basic information
beta-Alanine Chemical Properties
  • Melting point:202 °C (dec.)(lit.)
  • Boiling point:237.1±23.0 °C(Predicted)
  • Density 1,437 g/cm3
  • FEMA 3252 | BETA-ALANINE
  • refractive index 1.4650 (estimate)
  • Flash point:204-206°C
  • storage temp. Store at RT.
  • solubility H2O: 1 M at 20 °C, clear, colorless
  • form Crystalline Powder
  • pka3.55(at 25℃)
  • color White
  • PH6.0-7.5
  • Water Solubility Soluble in water(550g/L). Slightly soluble in alcohol. Insoluble in ether and acetone.
  • λmaxλ: 260 nm Amax: ≤0.02
    λ: 280 nm Amax: ≤0.02
  • Decomposition 204-206 ºC
  • JECFA Number1418
  • Merck 14,205
  • BRN 906793
  • Stability:Stable. Keep dry.
  • InChIKeyUCMIRNVEIXFBKS-UHFFFAOYSA-N
  • CAS DataBase Reference107-95-9(CAS DataBase Reference)
  • NIST Chemistry ReferenceBeta-alanine(107-95-9)
  • EPA Substance Registry System.beta.-Alanine (107-95-9)
Safety Information
  • Hazard Codes Xi
  • Risk Statements 36/37/38
  • Safety Statements 24/25-36-26
  • WGK Germany 3
  • RTECS UA2369200
  • TSCA Yes
  • HS Code 29224920
MSDS
beta-Alanine Usage And Synthesis
  • Chemical PropertiesWhite powder
  • DescriptionThis 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.
  • UsesIt 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.
  • Preparation
    • 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.
  • Descriptionβ-Alanine (or beta-alanine) is a naturally occurring beta amino acid, which is an amino acid in which the amino group is at the β- position from the carboxylate group (i.e., two atoms away. The IUPAC name for β-alanine is 3-amino propanoic acid. Unlike its counterpart α-alanine, β-alanine has no stereocenter.
    β-Alanine is not used in the biosynthesis of any major proteins or enzymes. It is formed in vivo by the degradation of dihydrouracil and carnosine. It is a component of the naturally occurring peptides carnosine and anserine and also of pantothenic acid (vitamin B5), which itself is a component of coenzyme A. Under normal conditions, β-alanine is metabolized into acetic acid.
    β-Alanine is the rate-limiting precursor of carnosine, which is to say carnosine levels are limited by the amount of available β-alanine. Supplementation with β-alanine has been shown to increase the concentration of carnosine in muscles, decrease fatigue in athletes and increase total muscular work done.
    Typically, studies have used supplementing strategies of multiple doses of 400 mg or 800 mg, administered at regular intervals for up to eight hours, over periods ranging from 4 to 10 weeks . After a 10 - week supplementing strategy, the reported increase in intramuscular carnosine content was an average of 80.1% (range 18 to 205%).
  • Chemical PropertiesThis 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.
  • Chemical PropertiesWhite crystalline powder
  • OccurrenceReported to occur as a component in amino acids; carnosine, anserine, pantothenic acid
  • Usesβ-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.
  • DefinitionChEBI: A naturally-occurring beta-amino acid comprising propionic acid with the amino group in the 3-position.
  • PreparationBy heating acrylic acid with concentrated aqueous ammonia under pressure, by addition of acrylonitrile to phthalimide or to ammonia; from β-aminopropionitrile, from succinimide by the Hofmann degradation.
  • Purification MethodsCrystallise 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.]
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