305-84-0 Usage
Description
L-Carnosine is a dipeptide composed of β-alanine and L-histidine, found in various tissues such as rat olfactory bulb, skeletal muscle, brain, kidney, and spleen, as well as human skeletal muscle. It exhibits diverse biological activities, including antioxidant, anti-aging, and anti-neoplastic properties. L-Carnosine has strong oxidant properties, as it can scavenge both reactive oxygen species (ROS) and reactive nitrogen species (RNS). It acts as a cytosolic buffering agent, a regulator of macrophage function, and a metal chelator that forms complexes with copper, cobalt, nickel, cadmium, or zinc.
Uses
Used in Pharmaceutical Applications:
L-Carnosine is used as an antioxidant for its ability to prevent cellular damage due to free radical activity. It is also used as an anti-aging agent, as it can help prevent or treat complications of diabetes, such as nerve damage, eye disorders (cataracts), and kidney problems. Additionally, L-Carnosine has potential therapeutic actions in antihypertensive effects, immunomodulation, wound healing, and antitumor/chemopreventive effects.
Used in Cosmetic Applications:
L-Carnosine is used as an anti-aging agent in cosmetics for its ability to improve skin condition and reduce the appearance of aging.
Used in Dietary Supplements:
L-Carnosine is used as a dietary supplement to reduce plasma levels of advanced glycation end products (AGEs) in diabetic rats, as well as to reduce brain edema, blood-brain barrier disruption, microglial activation, and neuronal apoptosis in a rat model of intracerebral hemorrhage.
Used in Medical Applications:
L-Carnosine is used as a treatment for gastritis, gastric ulcers, and dyspepsia symptoms when combined with zinc ions, as it has been used in Japan for these conditions. It is also used to reduce hepatic protein carbonylation and necrosis in a rat model of cirrhosis induced by bile duct ligation, as well as to reduce 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.
Reference
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
https://www.webmd.com/vitamins/ai/ingredientmono-1038/carnosine
G. M. Halpern, Zinc-Carnosine: Nature’s Safe and Effective Remedy for Ulcers, 2005, ISBN-10 0757002749
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
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.
Safety Profile
Mildly toxic by
intraperitoneal route. An experimental
teratogen. Other experimental reproductive
effects. When heated to decomposition it
emits toxic fumes of NOx.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 305-84-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,0 and 5 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 305-84:
(5*3)+(4*0)+(3*5)+(2*8)+(1*4)=50
50 % 10 = 0
So 305-84-0 is a valid CAS Registry Number.
InChI: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
305-84-0Relevant articles and documents
Molecular identification of carnosine synthase as ATP-grasp domain-containing protein 1 (ATPGD1)
Drozak, Jakub,Veiga-da-Cunha, Maria,Vertommen, Didier,Stroobant, Vincent,Van Schaftingen, Emile
, p. 9346 - 9356 (2010)
Carnosine (β-alanyl-L-histidine) and homocarnosine (γ-aminobutyryl-L-histidine) are abundant dipeptides in skeletal muscle and brain of most vertebrates and some invertebrates. The formation of both compounds is catalyzed by carnosine synthase, which is thought to convert ATP to AMP and inorganic pyrophosphate, and whose molecular identity is unknown. In the present work, we have purified carnosine synthase from chicken pectoral muscle about 1500-fold until only two major polypeptides of 100 and 90 kDa were present in the preparation. Mass spectrometry analysis of these polypeptides did not yield any meaningful candidate. Carnosine formation catalyzed by the purified enzyme was accompanied by a stoichiometric formation, not of AMP, but of ADP, suggesting that carnosine synthase belongs to the "ATP-grasp family" of ligases. A data base mining approach identified ATPGD1 as a likely candidate. As this protein was absent from chicken protein data bases, we reconstituted its sequence from a PCR-amplified cDNA and found it to fit with the 100-kDa polypeptide of the chicken carnosine synthase preparation. Mouse and human ATPGD1 were expressed in HEK293T cells, purified to homogeneity, and shown to catalyze the formation of carnosine, as confirmed by mass spectrometry, and of homocarnosine. Specificity studies carried out on all three enzymes were in agreement with published data. In particular, they acted with 15-25-fold higher catalytic efficiencies on β-alanine than on γ-aminobutyrate. The identification of the gene encoding carnosine synthase will help for a better understanding of the biological functions of carnosine and related dipeptides, which still remain largely unknown.
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Kroll,Hoberman
, p. 2511 (1953)
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Solid-phase peptide synthesis of dipeptide (histidine-β-Alanine) as a chelating agent by using trityl chloride resin, for removal of Al3+, Cu2+, Hg2+ and Pb2+: Experimental and theoretical study
Rahimi, Rahmatollah,Khosravi, Maryam,Tehrani, Mohammd H. H.,Rabbani, Mahboubeh,Safavi, Ebrahim
, p. 1814 - 1819 (2016)
Solid-phase peptide synthesis of dipeptide (histidine-β-Alanine) as a chelating agent examined by common N-9-fluorenylmethyloxycarbonyl-N-Trityl-L-histidine and tert-butyloxycarbonyl-β-Alanine-OH amino acid derivatives. Trityl chloride resin was used as a carrier resin. The molecular structure of the dipeptide was definite by using different methods such as ultraviolet visible (UV-Vis), Fourier transform infrared (FTIR), proton (1H) nuclear magnetic ressonance (NMR) and liquid chromatography-mass spectrometry (LC-MS) and the chelating property of synthesized dipeptide was investigated for removing of metal ions Al3+, Cu2+, Hg2+ and Pb2+ in vitro. In addition, the pharmacological and biological activities of dipeptide were examined by prediction of activity spectra for substances (PASS) program.
METHODS AND COMPOSITIONS FOR RAPIDLY DECREASING EPIGENETIC AGE AND RESTORATION OF MORE YOUTHFUL FUNCTION
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, (2020/03/01)
Disclosed are methods and compositions of reducing the epigenetic age of mammalian organism, especially an adult human of geriatric age. The methods provide for the proliferation of endogenous stem cells using mitochondrial fusion and a UCP2 blocker or other stimulants; supplying stem cells with nutrition to prevent cell cycle arrest; and removal of senescent somatic cells using senolytic treatments. The proliferation of endogenous neural stem cells after plaque removal for the treatment of Alzheimer's is also disclosed.
METHOD FOR PRODUCING L-CARNOSINE DERIVATIVE AND L-CARNOSINE
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, (2019/12/05)
PROBLEM TO BE SOLVED: To provide a convenient method for producing a high-purity N-protected L-carnosine derivative and L-carnosine. SOLUTION: A production method includes reacting an acid halide (1) with an L-histidine derivative (2). (R1 and R2 are H or a protection group of an amino group; X is a halogen atom). (A TMS group is a trimethylsilyl group). SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT