Chemical compound
Carnosine
Names
IUPAC name
β-Alanylhistidine
Systematic IUPAC name
(2S )-2-(3-Aminopropanamido)-3-(3H -imidazol-4-yl)propanoic acid
Other names
β-Alanyl-L -histidine
Identifiers
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.005.610
KEGG
UNII
InChI=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
Y Key: CQOVPNPJLQNMDC-ZETCQYMHSA-N
Y 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
Key: CQOVPNPJLQNMDC-ZETCQYMHBX
O=C(O)C(NC(=O)CCN)Cc1c[nH]cn1
c1c(nc[nH]1)C[C@@H](C(=O)O)NC(=O)CCN
Properties
C 9 H 14 N 4 O 3
Molar mass
226.236 g·mol−1
Appearance
Crystalline solid
Melting point
253 °C (487 °F; 526 K) (decomposition)
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
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 .[citation needed ] Carnosine was discovered by Russian chemist Vladimir Gulevich .[ 1]
Carnosine is naturally produced by the body in the liver[ 2] from beta-alanine and histidine . Like carnitine , carnosine is composed of the root word carn , meaning "flesh", alluding to its prevalence in meat.[ 3] There are no plant-based sources of carnosine.[ 4] Carnosine is readily available as a synthetic nutritional supplement.
^ Gulewitsch, Wl.; Amiradžibi, S. (1900). "Ueber das Carnosin, eine neue organische Base des Fleischextractes" . Berichte der Deutschen Chemischen Gesellschaft . 33 (2): 1902–1903. doi :10.1002/cber.19000330275 .
^ 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 (2015-07-15). "International society of sports nutrition position stand: Beta-Alanine" . Journal of the International Society of Sports Nutrition . 12 : 30. doi :10.1186/s12970-015-0090-y . ISSN 1550-2783 . PMC 4501114 . PMID 26175657 .
^ Hipkiss, A. R. (2006). "Does chronic glycolysis accelerate aging? Could this explain how dietary restriction works?". Annals of the New York Academy of Sciences . 1067 (1): 361–8. Bibcode :2006NYASA1067..361H . doi :10.1196/annals.1354.051 . PMID 16804012 . S2CID 41175541 .
^ Alan R. Hipkiss (2009). "Chapter 3: Carnosine and Its Possible Roles in Nutrition and Health". Advances in Food and Nutrition Research .