L-Carnosine
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L-Carnosine
structure -
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CAS No:
305-84-0
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Formula:
C9H14N4O3
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Chemical Name:
L-Carnosine
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Synonyms:
N-B-ALANYL-L-HISTIDINE;H-BETA-ALA-HIS-OH;L-IGNOTINE;L-BETA-ALANINE HISTIDINE;L-CARNOSINE;B-ALANYL-L-HISTIDINE;BETA-A-H;BETA-ALANYL-L-HISTIDINE
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CAS No:
Description
Crystalline
Solid
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.|Carnosine has been investigated for the treatment of Gulf War Illness.|Carnosine is a dipeptide comprised of a beta-alanine and a 3-methyl-L-histidine, which is found in dietary red meat, with potential antioxidant, metal-chelating and anti-glycation activities. Carnosine scavenges both reactive oxygen species (ROS) and unsaturated aldehydes produced by cell membrane lipid peroxidation. Additionally, this dipeptide may reduce the rate of formation of advanced glycation end-products (AGE). Altogether, this may protect cells against oxidative damage. In addition, carnosine is able to chelate toxic metals.|A naturally occurring dipeptide neuropeptide found in muscles.
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.
white to off-white crystalline.
L-Carnosine Basic Attributes
226.23
226.23
87671
206-169-9
8HO6PVN24W
TSCA listed
DTXSID7048615
C118880
White
29332900
Characteristics
121
-4
White crystalline
1.2673 (rough estimate)
253 °C (dec.) (lit.)
367.84°C (rough estimate)
350.7ºC
21 ° (C=2, H2O)
almost transparency
2-8°C
0Pa at 25℃
LD50 oral in mouse: > 14930mg/kg
Thermal decomposition to emit toxic nitrogen oxide fumes
20.9 º (c=1.5, H2O)
at 100.00%. odorless
2.62(at 25℃)
151 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|149.72 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|152.18 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]|154.1 Ų [M-H]- [CCS Type: DT, Method: stepped-field]|154.93 Ų [M-H]- [CCS Type: DT, Method: stepped-field]|150.8 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|154.7 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|152.1 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|153.1 Ų [M-H]-
-20°C
Safety Information
2
Xn
24/25-36-26
MS3080000
Xn
The warehouse is low-temperature, ventilated and dry
Stable, but may be heat sensitive - store cold. Incompatible with strong oxidizing agents.
P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362
20/21/22-36/37/38
Not Classified
L-Carnosine Use and Manufacturing
In the last step of the synthesis, peptide was cleaved from the resin with a mixture of TFA (1 mL), anizol(0.3 mL), phenol (0.3 g) and was shaken mechanically atroom temperature for 2 h. One important considerationwhen selecting the cleavage cocktail are scavengers, such asanizol, phenol, triisopropylsilane (TIPS), 1, 2-ethanedithiol(EDT), thioanisole or water. The reason the scavengers areoften added is because during the course of cleavage, highlyreactive cationic species can be generated, which can causedamage to the structure. The purpose of a scavenger is toextinguish any reactive species that may be generated duringrevelation from TFA cleavage. At the end of 2 h, the resin was filtered and washed with DMF (5 mL × 3) and after that with DCM (5 mL × 3). The filtrate was evaporated underreduced pressure and the resulting mixture precipitatedby adding diethylether (chemical formula = C9H14N4O3, molar mass = 226.23 g mol−1, melting point = 258 °C, yield = 90percent; Scheme 4). Boc is acid labile and sensitive toacid cleavage. A common process used to cleave the Boc offthe amine while on a solid phase resin is to add a solutionof 1:1 TFA in DCM (10 mL) at room temperature for 1 h.The amine will form a TFA salt and must be washed with3 successive steps of 1:1 DCM and DIPEA (10 mL g−1resin) to prepare the deprotected amine product for thenext addition step. If using 2-chlorotritylchloride resin, thiswill also cleave it, forming the resin as well as the amine.It is recommended to use a base labile resin if one needs toremove the Boc for further alkylation prior to deprotectionfrom a resin.15 (Yield = 90percent, melting point = 258 °C).Elemental analysis: calculated C (47.78percent), H (6.24percent), N (24.77percent), O (21.22percent). Molecular formula: C9H14N4O3;formula weight: 226.2324.
L-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 actions as neurotransmitters, modulation of enzymic activities and chelation of heavy metals.
L-Histidine, .beta.-alanyl-: ACTIVE
Computed Properties
Molecular Weight:226.23
XLogP3:-4
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:6
Exact Mass:226.10659032
Monoisotopic Mass:226.10659032
Topological Polar Surface Area:121
Heavy Atom Count:16
Complexity:259
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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