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Skeletal formula of beta alanine
Ball-and-stick model of the β-alanine molecule as a zwitterion
IUPAC name
3-Aminopropanoic acid
Other names
3-Aminopropionic acid
107-95-9 YesY
ChEBI CHEBI:16958 YesY
ChEMBL ChEMBL297569 YesY
ChemSpider 234 YesY
DrugBank DB03107 YesY
ECHA InfoCard 100.003.215
EC Number 203-536-5
Jmol 3D model Interactive image
KEGG D07561 YesY
PubChem 239
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
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):
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 verify (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.[3] 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.[4][5] 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.[3]

Figure 1: Comparison of β-alanine (right) with the more customary (chiral) amino acid, L-α-alanine (left)

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,[6] 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),[7] 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.

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).[8]

Athletic performance enhancement[edit]

Daily β-alanine supplementation can safely increase exercise performance, especially in exercise tasks lasting 1–4 minutes.[9][10]

Ingestion of β-Alanine can cause paraesthesia, reported as a tingling sensation, in a dose-dependent fashion.[9]


Sources for β-alanine includes pyrimidine catabolism of cytosine and uracil.

β-alanine can undergo a transanimation 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.[11]

Alternatively, β-alanine can be diverted into Pantothenate and Coenzyme A biosynthesis.[11]

Other uses[edit]

A high-potency artificial sweetener, called suosan, is derived from β-alanine.[12]


  1. ^ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.), Merck, 1989, ISBN 091191028X , 196.
  2. ^ Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-83. ISBN 0-8493-0462-8. .
  3. ^ a b
  4. ^ Derave W, Ozdemir MS, Harris R, Pottier A, Reyngoudt H, Koppo K, Wise JA, Achten E (August 9, 2007). "Beta-alanine supplementation augments muscle carnosine content and attenuates fatigue during repeated isokinetic contraction bouts in trained sprinters". J Appl Physiol. 103 (5): 1736–43. doi:10.1152/japplphysiol.00397.2007. PMID 17690198. 
  5. ^ Hill CA, Harris RC, Kim HJ, Harris BD, Sale C, Boobis LH, Kim CK, Wise JA (2007). "Influence of beta-alanine supplementation on skeletal muscle carnosine concentrations and high intensity cycling capacity". Amino Acids. 32 (2): 225–33. doi:10.1007/s00726-006-0364-4. PMID 16868650. 
  6. ^ Bate-Smith, EC (1938). "The buffering of muscle in rigor: protein, phosphate and carnosine". Journal of Physiology. 92 (3): 336–343. PMC 1395289free to read. PMID 16994977. 
  7. ^ Mannion, AF; Jakeman, PM; Dunnett, M; Harris, RC; Willan, PLT (1992). "Carnosine and anserine concentrations in the quadriceps femoris muscle of healthy humans". Eur. J. Appl. Physiol. 64: 47–50. doi:10.1007/BF00376439. 
  8. ^ Encyclopedia of Life Sciences Amino Acid Neurotransmitters. Jeremy M Henley, 2001 John Wiley & Sons, Ltd. doi:10.1038/npg.els.0000010, Article Online Posting Date: April 19, 2001
  9. ^ a b Trexler, Eric T.; Smith-Ryan, Abbie E.; Stout, Jeffrey R.; Hoffman, Jay R.; Wilborn, Colin D.; Sale, Craig; Kreider, Richard B.; Jäger, Ralf; Earnest, Conrad P.; Bannock, Laurent; Campbell, Bill; Kalman, Douglas; Ziegenfuss, Tim N.; Antonio, Jose (2015). "International society of sports nutrition position stand: Beta-Alanine". Journal of the International Society of Sports Nutrition. 12 (1). doi:10.1186/s12970-015-0090-y. ISSN 1550-2783. 
  10. ^ Beck, Kathryn; Thomson, Jasmine S; Swift, Richard J; von Hurst, Pamela R (2015). "Role of nutrition in performance enhancement and postexercise recovery". Open Access Journal of Sports Medicine: 259. doi:10.2147/OAJSM.S33605. ISSN 1179-1543. 
  11. ^ a b "KEGG PATHWAY: beta-Alanine metabolism - Reference pathway". Retrieved 2016-10-04. 
  12. ^ Aspartic acid-beta-4-nitroanilide in the ChemIDplus database

External links[edit]