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Beta-Alanine

β-Alanine
Skeletal formula of beta alanine
Ball-and-stick model of the β-alanine molecule as a zwitterion
Names
IUPAC name
3-Aminopropanoic acid
Other names
β-Alanine
3-Aminopropionic acid
Identifiers
107-95-9 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:16958 YesY
ChEMBL ChEMBL297569 YesY
ChemSpider 234 YesY
DrugBank DB03107 YesY
ECHA InfoCard 100.003.215
EC Number 203-536-5
2365
KEGG D07561 YesY
PubChem 239
UNII 11P2JDE17B YesY
Properties
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) 3.63
Hazards
Main hazards Irritant
Safety data sheet [1]
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 1000 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

β-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, see Figure 1). The IUPAC name for β-alanine is 3-aminopropanoic 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, not histidine. 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. 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.

L-Histidine, with a pKa of 6.1 is a relatively weak buffer over the physiological intramuscular pH range. However, when bound to other amino acids, this increases nearer to 6.8-7.0. In particular, when bound to β-alanine, the pKa value is 6.83, making this a very efficient intramuscular buffer. Furthermore, because of the position of the beta amino group, β-alanine dipeptides are not incorporated into proteins, and thus can be stored at relatively high concentrations (millimolar). Occurring at 17–25 mmol/kg (dry muscle), 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.


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