N-Acetyl carnosine Chemical Properties

Melting point:

209-210°C

Boiling point:

775.9±60.0 °C(Predicted)

Density 

1.343±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

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|

N-Acetyl carnosine Usage And Synthesis

Description

N-acetyl-L-Carnosine is a dipeptide and acetylated form of L-carnosine that has been found in heart and skeletal muscle and has antioxidant and anticataract activities. It reduces iron- and ascorbate-induced malondialdehyde (MDA) accumulation in liposomes when used at concentrations of 10 and 20 mM. Topical administration of N-acetyl-L-carnosine (1% v/v) reduces cortical opacities in a canine model of age-related cataracts.

Chemical Properties

White Crystalline Solid

Uses

N-acetyl-L-Carnosine is 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.

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

IC 50

Human Endogenous Metabolite

References

[1] Patent: CN105461632, 2016, A. Location in patent: Paragraph 0046

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