ChemicalBook Product Catalog Biochemical Engineering Amino Acids and Derivatives Other Amino Acid Protection N-Acetyl carnosine

N-Acetyl carnosine

Product NameN-Acetyl carnosine
CAS56353-15-2
MFC11H16N4O4
MW268.27
EINECS260-123-2
MOL File56353-15-2.mol

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
Cosmetics Ingredients Functions	SKIN PROTECTING
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\|

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

3025-95-4

71-00-1

56353-15-2

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

Preparation Products And Raw materials