Carnosine

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Chemical compound

title: "Carnosine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["dipeptides", "anti-aging-substances", "dietary-supplements"] description: "Chemical compound" topic_path: "general/dipeptides" source: "https://en.wikipedia.org/wiki/Carnosine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Watchedfields = changed | verifiedrevid = 443507179 | Reference = | ImageFile_Ref = | ImageFile = Carnosine.svg | IUPACName = β-Alanylhistidine | SystematicName = (2S)-2-(3-Aminopropanamido)-3-(3H-imidazol-4-yl)propanoic acid | OtherNames = β-Alanyl-L-histidine | Section1 = {{Chembox Identifiers | IUPHAR_ligand = 4559 | ChemSpiderID_Ref = | ChemSpiderID = 388363 | UNII_Ref = | UNII = 8HO6PVN24W | KEGG_Ref = | KEGG = C00386 | InChI =1/C9H14N4O3/c10-2-1-8(14)13-7(9(15)16)3-6-4-11-5-12-6/h4-5,7H,1-3,10H2,(H,11,12)(H,13,14)(H,15,16)/t7-/m0/s1 | InChIKey = CQOVPNPJLQNMDC-ZETCQYMHBX | ChEMBL_Ref = | ChEMBL = 242948 | StdInChI_Ref = | StdInChI = 1S/C9H14N4O3/c10-2-1-8(14)13-7(9(15)16)3-6-4-11-5-12-6/h4-5,7H,1-3,10H2,(H,11,12)(H,13,14)(H,15,16)/t7-/m0/s1 | StdInChIKey_Ref = | StdInChIKey = CQOVPNPJLQNMDC-ZETCQYMHSA-N | SMILES1 = c1c(nc[nH]1)CC@@HNC(=O)CCN | CASNo_Ref = | CASNo = 305-84-0 | PubChem = 439224 | ChEBI_Ref = | ChEBI = 15727 | SMILES = O=C(O)C(NC(=O)CCN)Cc1c[nH]cn1

| Section2 = {{Chembox Properties | C=9 | H=14 | N=4 | O=3 | Appearance = Crystalline solid | Density = | MeltingPtC = 253 | MeltingPt_notes = (decomposition) | BoilingPt = | Solubility =

| Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt =

Carnosine (beta-alanyl-L-histidine) is a dipeptide molecule, made up of the amino acids beta-alanine and histidine. It is highly concentrated in muscle and brain tissues. Carnosine was discovered by Russian chemist Vladimir Gulevich.

Carnosine is naturally produced by the body in the liver from beta-alanine and histidine. Like carnitine, carnosine is composed of the root word carn, meaning "flesh", alluding to its prevalence in meat. There are no plant-based sources of carnosine. Carnosine is readily available as a synthetic nutritional supplement.

Carnosine can chelate divalent metal ions. Carnosine is also considered a geroprotectant.

Products containing carnosine are also used in topical preparations to reduce wrinkles on the skin.

Carnosine may increase the Hayflick limit in human fibroblasts, it also appears to reduce the rate of telomere shortening. This could potentially promote the growth of certain cancers that thrive due to telomere preservation.

Biosynthesis

Carnosine is synthesized within the body from beta-alanine and histidine. Beta-alanine is a product of pyrimidine catabolism and histidine is an essential amino acid. Since beta-alanine is the limiting substrate, supplementing just beta-alanine effectively increases the intramuscular concentration of carnosine.

Physiological effects

pH buffer

Carnosine has a pKa value of 6.83, making it a good buffer for the pH range of animal muscles. Since beta-alanine is not incorporated into proteins, carnosine 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.

Anti-oxidant

Carnosine has been shown to scavenge reactive oxygen species (ROS) as well as alpha-beta unsaturated aldehydes formed from peroxidation of cell membrane fatty acids during oxidative stress. It also buffers pH in muscle cells, and acts as a neurotransmitter in the brain. It is also a zwitterion, a neutral molecule with a positive and negative end.

Antiglycating

Carnosine acts as an antiglycating agent, reducing the rate of formation of advanced glycation end-products (substances that can be a factor in the development or worsening of many degenerative diseases, such as diabetes, atherosclerosis, chronic kidney failure, and Alzheimer's disease), and ultimately reducing development of atherosclerotic plaque build-up.

Geroprotective

Carnosine is considered as a geroprotector. Carnosine can increase the Hayflick limit in human fibroblasts, as well as appearing to reduce the telomere shortening rate. Carnosine may also slow aging through its anti-glycating properties (chronic glycolyating is speculated to accelerate aging).

Other

Carnosine can chelate divalent metal ions. It has been suggested that binding Ca2+ may displace protons, thereby providing a link between Ca2+ and H+ buffering. However, there is still controversy as to how much Ca2+ is bound to carnosine under physiological conditions.

References

References

  1. Gulewitsch, Wl.. (1900). "Ueber das Carnosin, eine neue organische Base des Fleischextractes". Berichte der Deutschen Chemischen Gesellschaft.
  2. Trexler, Eric T.. (2015-07-15). "International society of sports nutrition position stand: Beta-Alanine". Journal of the International Society of Sports Nutrition.
  3. Hipkiss, A. R.. (2006). "Does chronic glycolysis accelerate aging? Could this explain how dietary restriction works?". Annals of the New York Academy of Sciences.
  4. Alan R. Hipkiss. (2009). "Advances in Food and Nutrition Research".
  5. (2005). "Carnosine: A Versatile Antioxidant and Antiglycating Agent".
  6. (2010). "Carnosine as a natural antioxidant and geroprotector: From molecular mechanisms to clinical trials".
  7. (2010). "Sex-specific serum biomarker patterns in adults with Asperger's syndrome".
  8. (2004). "L-Carnosine reduces telomere damage and shortening rate in cultured normal fibroblasts".
  9. "beta-ureidopropionate + H2O => beta-alanine + NH4+ + CO2".
  10. (August 9, 2007). "Beta-alanine supplementation augments muscle carnosine content and attenuates fatigue during repeated isokinetic contraction bouts in trained sprinters". J Appl Physiol.
  11. (2007). "Influence of beta-alanine supplementation on skeletal muscle carnosine concentrations and high intensity cycling capacity". Amino Acids.
  12. Bate-Smith, EC. (1938). "The buffering of muscle in rigor: protein, phosphate and carnosine". Journal of Physiology.
  13. Mannion, AF. (1992). "Carnosine and anserine concentrations in the quadriceps femoris muscle of healthy humans". Eur. J. Appl. Physiol.
  14. Vistoli, G. (Aug 2013). "Advanced glycoxidation and lipoxidation end products (AGEs and ALEs): an overview of their mechanisms of formation.". Free Radic. Res..
  15. Reddy, V. P.. (2005). "Carnosine: A Versatile Antioxidant and Antiglycating Agent". Science of Aging Knowledge Environment.
  16. Rashid, Imran. (2007). "Carnosine and its constituents inhibit glycation of low-density lipoproteins that promotes foam cell formation in vitro". FEBS Letters.
  17. Hipkiss, A. R.. (2005). "Glycation, ageing and carnosine: Are carnivorous diets beneficial?". Mechanisms of Ageing and Development.
  18. Boldyrev, A. A.. (2010). "Carnosine as a natural antioxidant and geroprotector: From molecular mechanisms to clinical trials". Rejuvenation Research.
  19. McFarland, G. (1994). "Retardation of the Senescence of Cultured Human Diploid Fibroblasts by Carnosine". Experimental Cell Research.
  20. Shao, Lan. (2004). "L-Carnosine reduces telomere damage and shortening rate in cultured normal fibroblasts". Biochemical and Biophysical Research Communications.
  21. Hipkiss, A. R.. (2006). "Does Chronic Glycolysis Accelerate Aging? Could This Explain How Dietary Restriction Works?". Annals of the New York Academy of Sciences.
  22. Abate, Chiara. (2021). "Understanding the behaviour of carnosine in aqueous solution: an experimental and quantum-based computational investigation on acid–base properties and complexation mechanisms with Ca 2+ and Mg 2+". New Journal of Chemistry.
  23. Swietach, Pawel. (2013-05-28). "Coupled Ca2+/H+ transport by cytoplasmic buffers regulates local Ca2+ and H+ ion signaling". Proceedings of the National Academy of Sciences of the United States of America.
  24. Eisner, David. (2023-06-16). "Physiology of intracellular calcium buffering". Physiological Reviews.

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