Acetylcarnosine

Base Information

• Chemical Name: Acetylcarnosine
• CAS No.: 56353-15-2
• Molecular Formula: C11H16 N4 O4
• Molecular Weight: 268.272
• Hs Code.: 2942000000
• Wikipedia: Acetylcarnosine
• Wikidata: Q76415296
• Metabolomics Workbench ID: 42124
• Mol file: 56353-15-2.mol

Synonyms:Acetylcarnosine;(2R)-2-(3-acetamidopropanoylamino)-3-(1H-imidazol-5-yl)propanoic acid;(2R)-2-(3-acetamidopropanamido)-3-(1H-imidazol-4-yl)propanoic acid;79743-14-9;CHEBI:172509;EN300-6758708;(2R)-2-(3-acetamidopropanamido)-3-(1H-imidazol-5-yl)propanoic acid

Chemical Property of Acetylcarnosine

Chemical Property:

• Appearance/Colour: white to off-white powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 253 - 260 C
• Boiling Point: 775.9 °C at 760 mmHg
• PKA: 3.08±0.10(Predicted)
• Flash Point: 423 °C
• PSA: 124.18000
• Density: 1.343 g/cm³
• LogP: -0.17040
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 268.11715500
• Heavy Atom Count: 19
• Complexity: 348

Purity/Quality:

99% up ^*data from raw suppliers

N-Acetyl-L-carnosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): UN NO.
• Hazard Codes: UN NO.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NCCC(=O)NC(CC1=CN=CN1)C(=O)O
• Isomeric SMILES: CC(=O)NCCC(=O)N[C@H](CC1=CN=CN1)C(=O)O
• 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.
• Uses: N-acetyl-L-Carnosine is used in the treatment of cataracts and in the treatment of UV-induced immunosuppression

Technology Process of Acetylcarnosine

There total 5 articles about Acetylcarnosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.9%

N-acetyl-β-alanine (3025-95-4) + L-histidine (71-00-1) → N-acetyl-β-alanyl-L-histidine (56353-15-2)

Guidance literature:

With 2-chloro-1,3-dimethylimidazolinium chloride; In ethanol; at 40 ℃; for 3h; Concentration; Reagent/catalyst; Solvent; Temperature;

Reference yield:

N-acetyl-β-alanyl chloride + O-(Trimethylsilyl)histidine → N-acetyl-β-alanyl-L-histidine (56353-15-2)

Guidance literature:

N-acetyl-β-alanyl chloride; O-(Trimethylsilyl)histidine; In chloroform; at -1 - 10 ℃; for 3h;

With water; In chloroform; at 30 ℃; for 2h; Temperature; Reagent/catalyst;

Reference yield:

N-acetyl-β-alanine (3025-95-4) → N-acetyl-β-alanyl-L-histidine (56353-15-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: thionyl chloride / chloroform / 3 h / 60 °C

2.1: chloroform / 3 h / -1 - 10 °C

2.2: 2 h / 30 °C

With thionyl chloride; In chloroform;

upstream raw materials:

N-acetyl-β-alanine

L-histidine

Refernces

• 1、 -. "Preparing method for N-acetyl-L-carnosine". Paragraph 0040. . Retrieved 2017/03/14.