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L-Carnosine

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CAS:305-84-0
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  • L-Carnosine
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L-Carnosine Basic information
Product Name:L-Carnosine
Synonyms:L-Histidine,beta-alanyl-;L-Carnosine (beta-Alanyl-L-histidine);β-Ala-His-OH;L-Carnosine,N-beta-Alanyl-L-histidine;H-BETA-ALA-HIS-OH;L-IGNOTINE;L-BETA-ALANINE HISTIDINE;L-CARNOSINE
CAS:305-84-0
MF:C9H14N4O3
MW:226.23
EINECS:206-169-9
Product Categories:amino;API;Nutritional Supplements;Amino Acids;chiral;Amino Acid Derivatives;Food additive;cosmestic;APIs;305-84-0
Mol File:305-84-0.mol
L-Carnosine Structure
L-Carnosine Chemical Properties
Melting point 253 °C (dec.) (lit.)
Boiling point 367.84°C (rough estimate)
alpha 20.9 º (c=1.5, H2O)
density 1.2673 (rough estimate)
vapor pressure 0Pa at 25℃
refractive index 21 ° (C=2, H2O)
storage temp. -20°C
solubility DMSO (Very Slightly), Water (Slightly)
form crystalline
pka2.62(at 25℃)
color White
Odorat 100.00?%. odorless
Water Solubility almost transparency
Merck 14,1850
BRN 87671
Stability:Stable, but may be heat sensitive - store cold. Incompatible with strong oxidizing agents.
InChIKeyCQOVPNPJLQNMDC-ZETCQYMHSA-N
LogP-3.8 at 22℃
CAS DataBase Reference305-84-0(CAS DataBase Reference)
EPA Substance Registry SystemL-Histidine, .beta.-alanyl- (305-84-0)
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22-36/37/38
Safety Statements 24/25-36-26
WGK Germany 2
RTECS MS3080000
3-10
TSCA Yes
HS Code 29332900
ToxicityLD50 oral in mouse: > 14930mg/kg
MSDS Information
ProviderLanguage
L-Carnosine English
SigmaAldrich English
ACROS English
L-Carnosine Usage And Synthesis
DescriptionL-Carnosine is a dipeptide composed of β-alanine and L-histidine that has been found in rat olfactory bulb, skeletal muscle, brain, kidney, and spleen tissues, as well as human skeletal muscle, and has diverse biological activities. It is a metal chelator that forms complexes with copper, cobalt, nickel, cadmium, or zinc. Dietary administration of L-carnosine (60 mg/kg per day) reduces plasma levels of advanced glycation end products (AGEs) in diabetic rats. It reduces brain edema, blood-brain barrier disruption, microglial activation, and neuronal apoptosis in a rat model of intracerebral hemorrhage when administered at a dose of 1,000 mg/kg. L-Carnosine (250, 500, and 1,000 mg/kg, i.p.) reduces hepatic protein carbonylation and necrosis in a rat model of cirrhosis induced by bile duct ligation. It also reduces lung myeloperoxidase (MPO) activity, production of reactive oxygen species (ROS), and TNF-α and IL-6 levels, as well as alveolar hemorrhage, interstitial edema, and pulmonary leukocyte infiltration in a mouse model of LPS-induced lung injury.
Chemical Propertieswhite to off-white crystalline.
HistoryCarnosine, a dipeptide composed of beta-alanine and L-histidine, was first identified in beef extracts by Russian chemists Gulewitch and Amiradzibi in 1900.
UsesL-Carnosine is a naturally-occurring histidine-containing compound and the biological role of this dipeptide is to act as cytosolic buffering agents. Other roles ascribed to L-Carnosine include action s as neurotransmitters, modulation of enzymic activities and chelation of heavy metals. Studies indicate an ability to boost the immunological functions. In cosmetics, it has anti-aging and skin-conditioning applications.
DefinitionChEBI: Carnosine is a dipeptide that is the N-(beta-alanyl) derivative of L-histidine. It has a role as an anticonvulsant, an antioxidant, an antineoplastic agent, a human metabolite, a Daphnia magna metabolite, a mouse metabolite, a neuroprotective agent and a geroprotector. It is a conjugate acid of a carnosinate. It is a tautomer of a carnosine zwitterion.
benefitsL-Carnosine is a strong anti-glycosylation, free radical scavenging,anti-oxidant,anti-aging, anti-pollution.Brightenand repairthe skin. white powder.Its recommended dosage is 0.05~2%.
Synthesis Reference(s)The Journal of Organic Chemistry, 48, p. 392, 1983 DOI: 10.1021/jo00151a026
General DescriptionCarnosine is a dipeptide comprising beta-alanine and histidine. It is found in muscular and other tissues. It has strong oxidant property as it can scavenge both reactive oxygen species (ROS) and reactive nitrogen species (RNS). Carnosine acts as a cytosolic buffering agent and as a regulator of macrophage function.1 Attributing to its ability to form complexes with transition metals, it is used to regulate the content of transition metal ions in biological fluids and tissues.
Carnosine can prevent aging and can be used to prevent or treat complications of diabetes such as nerve damage, eye disorders (cataracts), and kidney problems.2 Potential therapeutic actions of carnosine include antihypertensive effects, immunomodulation, would healing, and antitumor/chemopreventive effects. The chelate compound of zinc ion and carnosine has been used in Japan for gastritis, gastric ulcers, and dyspepsia symptoms.3
Biochem/physiol ActionsL-Carosine is a dipeptide found at millimolar concentration in brain, muscle and the lens of the eye. In model systems it is a potent antioxidant that scavenges oxygen free radicals and transition metal ions. It blocks protein-protein and protein-DNA cross-links induced by hypochlorite anions and toxic aldehydes such as acetaldehyde, formaldehyde, and malondialdehyde, the primary product of lipid peroxidation. It also inhibits nonenzymatic protein glycation induced by aldose and ketose reducing sugars and inhibits the formation of toxic advanced glycation end products (AGE). These activities make it of interest in studies of aging, atherosclerosis, Alzheimer′s disease, and the secondary effects of diabetes.
Side effects L-carnosine is generally considered safe when taken by mouth for short periods of time or when used by adults on the skin. However, there can be rare side effects, including rash, itchiness, dry mouth, changes in appetite, feelings of tiredness or vivid dreams. Rare but severe possible zinc carnosine side effects include decreased white blood cells, disorder of the digestive system and sideroblastic anemia. Less severe side effects may include stomach cramps, indigestion and nausea.
Safety ProfileMildly toxic by intraperitoneal route. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.
Purification MethodsLikely impurities are histidine and β-alanine. Crystallise L-carnosine from water by adding EtOH in excess. Recrystallise it from aqueous EtOH by slow addition of EtOH to a strong aqueous solution of the dipeptide. Its solubility in H2O is 33.3% at 25o. [Vinick & Jung J Org Chem 48 392 1983, Turner J Am Chem Soc 75 2388 1953, Sifford & du Vigneaud J Biol Chem 108 753 1935, Beilstein 25 H 516, 25 I 717, 25 II 408.]
References1. P. J. Quinn, A. A. Boldyrev, V. E. Formazuyk, Carnosine: Its properties, functions and potential therapeutic applications, Molecular Aspects of Medicine, 1992, vol. 13, pp. 379-444 DOI:10.1016/0098-2997(92)90006-L
2. https://www.webmd.com/vitamins/ai/ingredientmono-1038/carnosine
3. G. M. Halpern, Zinc-Carnosine: Nature’s Safe and Effective Remedy for Ulcers, 2005, ISBN-10 0757002749
4. l-Carnosine, a Substrate of Carnosinase-1, Influences Glucose Metabolism DOI:10.2337/db07-0177
5. L-carnosine (beta-alanyl-L-histidine) and carcinine (beta-alanylhistamine) act as natural antioxidants with hydroxyl-radical-scavenging and lipid-peroxidase activities. DOI:10.1042/BJ3040509
6. Boldyrev, A.A., Aldini, G., and Derave, W. Physiology and pathophysiology of carnosine. Physiol. Rev. 93(4), 1803-1845 (2013). DOI:10.1152/physrev.00039.2012
7. Ghodsi, R., and Kheirouri, S. Carnosine and advanced glycation end products: A systematic review. Amino Acids 50(9), 1177-1186 (2018). DOI:10.1007/s00726-018-2592-9
8. Tanaka, K.I., Sugizaki, T., Kanada, Y., et al. Preventive effects of carnosine on lipopolysaccharide-induced lung injury. Sci. Rep. 7:42813, (2017). DOI:10.1038/srep42813
L-Carnosine Preparation Products And Raw materials
Raw materialsD-Histidine-->tert-Butyl cyanoacetate
Tag:L-Carnosine(305-84-0) Related Product Information
β-Alanine L-Alanyl-L-Glutamine EC 2.3.2.2 L-Malic acid L-Tyrosine L-Aspartic acid Methyl (S)-(-)-lactate L-Valine L-carnitine L-Lysine L-Glutamine H-LEU-LEU-OH L-Pyroglutamic acid L(+)-Arginine CARNOSINE, L-(P),CARNOSINE, L-(RG) n-acetyl carnosine,N-ACETYL-L-CARNOSINE,N-Aceyl-L-Carnosine L-ANSERINE NITRATE ZINC CARNOSINE,zinc l-carnosine complex,Zinc L-Carnosine,Zn Carnosine,carnosine, zinc- Carnosine