Names | |
---|---|
IUPAC name
β-Alanine
| |
Systematic IUPAC name
3-Aminopropanoic acid | |
Other names
3-Aminopropionic acid
| |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.003.215 |
EC Number |
|
KEGG | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties [2] [3] | |
C3H7NO2 | |
Molar mass | 89.093 g/mol |
Appearance | white bipyramidal crystals |
Odor | odorless |
Density | 1.437 g/cm3 (19 °C) |
Melting point | 207 °C (405 °F; 480 K) (decomposes) |
54.5 g/100 mL | |
Solubility | soluble in methanol. Insoluble in diethyl ether, acetone |
log P | -3.05 |
Acidity (pKa) |
|
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
|
Irritant |
NFPA 704 (fire diamond) | |
Lethal dose or concentration (LD, LC): | |
LD50 (
median dose)
|
1000 mg/kg (rat, oral) |
Safety data sheet (SDS) | [1] |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
β-Alanine (or beta-alanine) is a naturally occurring beta amino acid, which is an amino acid in which the amino group is attached to the β-carbon (i.e. the carbon two carbon atoms away from the carboxylate group) instead of the more usual α-carbon for alanine (α-alanine). The IUPAC name for β-alanine is 3-aminopropanoic acid. Unlike its counterpart α-alanine, β-alanine has no stereocenter.
In terms of its biosynthesis, it is formed by the degradation of dihydrouracil and carnosine. β-Alanine ethyl ester is the ethyl ester which hydrolyses within the body to form β-alanine. [4] It is produced industrially by the reaction of ammonia with β-propiolactone. [5]
Sources for β-alanine includes pyrimidine catabolism of cytosine and uracil.
β-Alanine residues are rare. It is a component of the peptides carnosine and anserine and also of pantothenic acid (vitamin B5), which itself is a component of coenzyme A. 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, not histidine. [6] 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. [7] [8] Simply supplementing with carnosine is not as effective as supplementing with β-alanine alone since carnosine, when taken orally, is broken down during digestion to its components, histidine and β-alanine. Hence, by weight, only about 40% of the dose is available as β-alanine. [6]
Because β-alanine dipeptides are not incorporated into proteins, they can be stored at relatively high concentrations. Occurring at 17–25 mmol/kg (dry muscle), [9] carnosine (β-alanyl-L-histidine) is an important intramuscular buffer, constituting 10-20% of the total buffering capacity in type I and II muscle fibres. In carnosine, the pKa of the imidazolium group is 6.83, which is ideal for buffering. [10]
Even though much weaker than glycine (and, thus, with a debated role as a physiological transmitter), β-alanine is an agonist next in activity to the cognate ligand glycine itself, for strychnine-sensitive inhibitory glycine receptors (GlyRs) (the agonist order: glycine ≫ β-alanine > taurine ≫ alanine, L-serine > proline). [11]
β-alanine has five known receptor sites, including GABA-A, GABA-C a co-agonist site (with glycine) on NMDA receptors, the aforementioned GlyR site, and blockade of GAT protein-mediated glial GABA uptake, making it a putative "small molecule neurotransmitter." [12]
There is evidence that β-alanine supplementation can increase exercise and cognitive performance, [13] [14] [15] [16] for some sporting modalities, [17] and exercises within a 0.5–10 min time frame. [18] β-alanine is converted within muscle cells into carnosine, which acts as a buffer for the lactic acid produced during high-intensity exercises, and helps delay the onset of neuromuscular fatigue. [15] [19]
Ingestion of β-alanine can cause paraesthesia, reported as a tingling sensation, in a dose-dependent fashion. [16] Aside from this, no important adverse effect of β-alanine has been reported, however, there is also no information on the effects of its long-term usage or its safety in combination with other supplements, and caution on its use has been advised. [13] [14] Furthermore, many studies have failed to test for the purity of the supplements used and check for the presence of banned substances. [15]
β-Alanine can undergo a transamination reaction with pyruvate to form malonate-semialdehyde and L-alanine. The malonate semialdehyde can then be converted into malonate via malonate-semialdehyde dehydrogenase. Malonate is then converted into malonyl-CoA and enter fatty acid biosynthesis. [20]
Alternatively, β-alanine can be diverted into pantothenic acid and coenzyme A biosynthesis. [20]
{{
cite journal}}
: CS1 maint: numeric names: authors list (
link)
Names | |
---|---|
IUPAC name
β-Alanine
| |
Systematic IUPAC name
3-Aminopropanoic acid | |
Other names
3-Aminopropionic acid
| |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.003.215 |
EC Number |
|
KEGG | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties [2] [3] | |
C3H7NO2 | |
Molar mass | 89.093 g/mol |
Appearance | white bipyramidal crystals |
Odor | odorless |
Density | 1.437 g/cm3 (19 °C) |
Melting point | 207 °C (405 °F; 480 K) (decomposes) |
54.5 g/100 mL | |
Solubility | soluble in methanol. Insoluble in diethyl ether, acetone |
log P | -3.05 |
Acidity (pKa) |
|
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
|
Irritant |
NFPA 704 (fire diamond) | |
Lethal dose or concentration (LD, LC): | |
LD50 (
median dose)
|
1000 mg/kg (rat, oral) |
Safety data sheet (SDS) | [1] |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
β-Alanine (or beta-alanine) is a naturally occurring beta amino acid, which is an amino acid in which the amino group is attached to the β-carbon (i.e. the carbon two carbon atoms away from the carboxylate group) instead of the more usual α-carbon for alanine (α-alanine). The IUPAC name for β-alanine is 3-aminopropanoic acid. Unlike its counterpart α-alanine, β-alanine has no stereocenter.
In terms of its biosynthesis, it is formed by the degradation of dihydrouracil and carnosine. β-Alanine ethyl ester is the ethyl ester which hydrolyses within the body to form β-alanine. [4] It is produced industrially by the reaction of ammonia with β-propiolactone. [5]
Sources for β-alanine includes pyrimidine catabolism of cytosine and uracil.
β-Alanine residues are rare. It is a component of the peptides carnosine and anserine and also of pantothenic acid (vitamin B5), which itself is a component of coenzyme A. 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, not histidine. [6] 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. [7] [8] Simply supplementing with carnosine is not as effective as supplementing with β-alanine alone since carnosine, when taken orally, is broken down during digestion to its components, histidine and β-alanine. Hence, by weight, only about 40% of the dose is available as β-alanine. [6]
Because β-alanine dipeptides are not incorporated into proteins, they can be stored at relatively high concentrations. Occurring at 17–25 mmol/kg (dry muscle), [9] carnosine (β-alanyl-L-histidine) is an important intramuscular buffer, constituting 10-20% of the total buffering capacity in type I and II muscle fibres. In carnosine, the pKa of the imidazolium group is 6.83, which is ideal for buffering. [10]
Even though much weaker than glycine (and, thus, with a debated role as a physiological transmitter), β-alanine is an agonist next in activity to the cognate ligand glycine itself, for strychnine-sensitive inhibitory glycine receptors (GlyRs) (the agonist order: glycine ≫ β-alanine > taurine ≫ alanine, L-serine > proline). [11]
β-alanine has five known receptor sites, including GABA-A, GABA-C a co-agonist site (with glycine) on NMDA receptors, the aforementioned GlyR site, and blockade of GAT protein-mediated glial GABA uptake, making it a putative "small molecule neurotransmitter." [12]
There is evidence that β-alanine supplementation can increase exercise and cognitive performance, [13] [14] [15] [16] for some sporting modalities, [17] and exercises within a 0.5–10 min time frame. [18] β-alanine is converted within muscle cells into carnosine, which acts as a buffer for the lactic acid produced during high-intensity exercises, and helps delay the onset of neuromuscular fatigue. [15] [19]
Ingestion of β-alanine can cause paraesthesia, reported as a tingling sensation, in a dose-dependent fashion. [16] Aside from this, no important adverse effect of β-alanine has been reported, however, there is also no information on the effects of its long-term usage or its safety in combination with other supplements, and caution on its use has been advised. [13] [14] Furthermore, many studies have failed to test for the purity of the supplements used and check for the presence of banned substances. [15]
β-Alanine can undergo a transamination reaction with pyruvate to form malonate-semialdehyde and L-alanine. The malonate semialdehyde can then be converted into malonate via malonate-semialdehyde dehydrogenase. Malonate is then converted into malonyl-CoA and enter fatty acid biosynthesis. [20]
Alternatively, β-alanine can be diverted into pantothenic acid and coenzyme A biosynthesis. [20]
{{
cite journal}}
: CS1 maint: numeric names: authors list (
link)