| Identification | Back Directory | [Name]
N-Acetyl carnosine | [CAS]
56353-15-2 | [Synonyms]
Can-C
Acetyl Carnosine
AC-SS-ALA-HIS-OH
Ac-βAla-L-His-OH
N-Acetyl camosine
n-acetyl carnosine
N-Aceyl-L-Carnosine
N-ACETYL-L-CARNOSINE
Acetyl-beta-alanyl-histidine
N-Acetyl-L-carnosine, >=98.5%
N-Acetyl carnosine / Dipeptide
L-Histidine, N-acetyl-b-alanyl-
Ac-Beta-Ala-His-OH(L-Carnosine)
N-A-ACETYL-N-B-ALANYL-L-HISTIDINE
Nα-(N-Acetyl-β-alanyl)-L-histidine
L-Histidine, N-acetyl-.beta.-alanyl-
N-(N-acetyl-beta-alanyl)-L-histidine
NAC, N-a-Acetyl-N--alanyl-L-histidine
NAC, N-α-Acetyl-N-β-alanyl-L-histidine
NAC, N-a-Acetyl-N-b-alanyl-L-histidine
(S)-2-(3-AcetaMidopropanaMido)-3-(1H-iMidazol-4-yl)propanoic acid
(S)-2-(3-ACETYLAMINO-PROPIONYLAMINO)-3-(3H-IMIDAZOL-4-YL)-PROPIONIC ACID | [EINECS(EC#)]
260-123-2 | [Molecular Formula]
C11H16N4O4 | [MDL Number]
MFCD04039376 | [MOL File]
56353-15-2.mol | [Molecular Weight]
268.27 |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Solid | [Melting point ]
209-210°C | [Boiling point ]
775.9±60.0 °C(Predicted) | [density ]
1.343±0.06 g/cm3(Predicted) | [storage temp. ]
Hygroscopic, -20°C Freezer, Under Inert Atmosphere | [solubility ]
Methanol (Slightly), Water (Slightly) | [form ]
Solid | [pka]
3.08±0.10(Predicted) | [color ]
White to Off-White | [InChI]
InChI=1/C11H16N4O4/c1-7(16)13-3-2-10(17)15-9(11(18)19)4-8-5-12-6-14-8/h5-6,9H,2-4H2,1H3,(H,12,14)(H,13,16)(H,15,17)(H,18,19)/t9-/s3 | [InChIKey]
BKAYIFDRRZZKNF-DJEYLCQNNA-N | [SMILES]
[C@H](C(=O)O)(NC(=O)CCNC(=O)C)CC1N=CNC=1 |&1:0,r| |
| Hazard Information | Back Directory | [Chemical Properties]
White Crystalline Solid | [Uses]
Used in the treatment of cataracts and in the treatment of UV-induced immunosuppression | [Definition]
ChEBI: A dipeptide that is the N-acetyl derivative of carnosine. | [Description]
N-acetyl-L-Carnosine is a dipeptide and acetylated form of L-carnosine (Item No. 29825) that has been found in heart and skeletal muscle and has antioxidant and anticataract activities.1,2 It reduces iron- and ascorbate-induced malondialdehyde (MDA) accumulation in liposomes when used at concentrations of 10 and 20 mM.1 Topical administration of N-acetyl-L-carnosine (1% v/v) reduces cortical opacities in a canine model of age-related cataracts.2 | [Synthesis]
In a 500 mL three-necked flask, 300 mL of anhydrous ethanol was added and 80 g (0.611 mol) of N-acetyl-β-alanine and 86.1 g (0.555 mol) of L-histidine were sequentially added followed by 98 g (0.582 mol) of N,N'-dimethylcarbodiimide (DMC). The reaction mixture was heated to 40°C and the reaction was kept stirring for 3 hours. Upon completion of the reaction, the reaction solution was cooled to 5°C, a solid was precipitated and the solid product was collected by filtration. The filter cake was washed with 150 mL of anhydrous ethanol and dried under vacuum to give 145 g of (S)-2-(3-acetamidopropionamide)-3-(1H-imidazol-4-yl)propanoic acid (IV) in 97.9% yield and >98.8% HPLC purity. | [in vivo]
Right eyes of the rabbits (male grey chinchilla rabbits aged 3-4 months weighing 2-3 k) are instilled with 80 μL of formulation A containing 1 % N-Acetylcarnosine. The N-Acetylcarnosine prodrug eye drops optimize the clinical effects for the treatment of ophthalmic disorders (such as prevention and reversal of cataracts in human and animal eyes)[1]. | [IC 50]
Human Endogenous Metabolite | [References]
[1] Patent: CN105461632, 2016, A. Location in patent: Paragraph 0046 |
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