| Identification | More | [Name]
L-Carnosine | [CAS]
305-84-0 | [Synonyms]
B-ALANYL-L-HISTIDINE
BETA-A-H
BETA-ALA-HIS
BETA-ALA-L-HIS
BETA-ALANYL-L-HISTIDINE
CARNOSINE
CARNOSINE, L-
H-BETA-ALA-HIS-OH
L-BETA-ALANINE HISTIDINE
L-CARNOSINE
L-IGNOTINE
N-B-ALANYL-L-HISTIDINE
N-BETA-ALANYL-L-HISTIDINE
beta-Alanyl-histidine
ignotine
karnozzn
n-2-m
Nalpha-(beta-alanyl)-L-histidine
n-beta-alanyl-l-histidin
β-Alanyl-L-histidine
| [EINECS(EC#)]
206-169-9 | [Molecular Formula]
C9H14N4O3 | [MDL Number]
MFCD00005207 | [Molecular Weight]
226.23 | [MOL File]
305-84-0.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystalline | [Melting point ]
253 °C (dec.) (lit.) | [alpha ]
20.9 º (c=1.5, H2O) | [Boiling point ]
367.84°C (rough estimate) | [density ]
1.2673 (rough estimate) | [vapor pressure ]
0Pa at 25℃ | [refractive index ]
21 ° (C=2, H2O) | [storage temp. ]
2-8°C
| [solubility ]
DMSO (Very Slightly), Water (Slightly) | [form ]
crystalline
| [pka]
2.62(at 25℃) | [color ]
White | [Odor]
at 100.00?%. odorless | [Stability:]
Stable, but may be heat sensitive-store cold. Incompatible with strong oxidizing agents. | [Optical Rotation]
+24.120 | [Water Solubility ]
almost transparency | [Merck ]
1850 | [BRN ]
87671 | [Major Application]
food and beverages
personal care
pharmaceutical | [Cosmetics Ingredients Functions]
SKIN CONDITIONING | [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 | [InChIKey]
CQOVPNPJLQNMDC-ZETCQYMHSA-N | [SMILES]
NCCC(=O)N[C@@H](Cc1c[nH]cn1)C(O)=O | [LogP]
-3.8 at 22℃ | [Uses]
carnosine is an anti-oxidant that works to prevent cellular damage because of free radical activity. Studies indicate an ability to boost the immunological functions. Carnosine is a naturally occurring amino acid. In cosmetics, it has anti-aging and skin-conditioning applications. | [CAS DataBase Reference]
305-84-0(CAS DataBase Reference) | [EPA Substance Registry System]
305-84-0(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319 | [Precautionary statements ]
P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
2
| [RTECS ]
MS3080000
| [F ]
3-10 | [TSCA ]
Yes | [REACH Registrations]
Active | [HS Code ]
29332900 | [Storage Class]
11 - Combustible Solids | [Safety Profile]
Mildly toxic by
intraperitoneal route. An experimental
teratogen. Other experimental reproductive
effects. When heated to decomposition it
emits toxic fumes of NOx. | [Toxicity]
LD50 oral in mouse: > 14930mg/kg |
| Hazard Information | Back Directory | [Description]
L-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 Properties]
white to off-white crystalline. | [History]
Carnosine, a dipeptide composed of beta-alanine and L-histidine, was first identified in beef extracts by Russian chemists Gulewitch and Amiradzibi in 1900. | [Application]
L-Carnosine has been used to study its effects as an antioxidant on meat quality of pigs. It has also been used to study its effects on brain injury in a rat intracerebral hemorrhage model. | [Definition]
ChEBI: 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. | [benefits]
L-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 Description]
Carnosine 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 | [Flammability and Explosibility]
Notclassified | [Biochem/physiol Actions]
L-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.
| [Synthesis]
A) Preparation of hydrazinolysis reaction solution, in a 1000 ml four-necked reaction flask, put in as an intermediate phthaloyl-L-creatinine 50 g (0.14 mol), 200 ml of water, hydrazine hydrate (mass percent concentration of 80%) 10.8 g (0.17 mol), hea | [storage]
Store at -20°C | [Purification Methods]
Likely 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.] | [References]
1. 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 |
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