L-Carnosine
[CAS# 305-84-0]

Identification

• Classification: Biochemical >> Peptide
• Name: L-Carnosine
• Synonyms: Carnosine; N-beta-Alanyl-L-histidine
• Molecular Formula: C₉H₁₄N₄O₃
• Molecular Weight: 226.23
• Protein Sequence: XH
• CAS Registry Number: 305-84-0
• EC Number: 206-169-9
• SMILES: C1=C(NC=N1)C[C@@H](C(=O)O)NC(=O)CCN

Properties

• Solubility: 322.0 g/kg
• Melting point: 253 °C
• alpha: 20.9 ° (c=1.5, H2O)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

L-Carnosine, a naturally occurring dipeptide composed of beta-alanine and histidine, was first isolated in 1900 by Russian chemist Vladimir Gulevich. It is predominantly found in the muscle and brain tissues of mammals. Gulevich's discovery stemmed from his interest in understanding the biochemical components of muscle tissue. Subsequent research over the decades has elucidated its various biological functions and potential therapeutic applications, positioning L-Carnosine as a significant molecule in the field of biochemistry and medicine.

L-Carnosine is widely recognized for its antioxidant properties. It scavenges reactive oxygen species (ROS) and protects cells from oxidative stress, which is implicated in aging and various chronic diseases. By neutralizing free radicals, L-Carnosine helps to maintain cellular integrity and function, making it a potential therapeutic agent for conditions such as Alzheimer's disease, Parkinson's disease, and cataracts.

One of the significant applications of L-Carnosine is its role as an anti-glycation agent. Glycation is a process where sugar molecules bind to proteins or lipids, leading to the formation of advanced glycation end-products (AGEs). These AGEs contribute to the aging process and the development of diabetic complications. L-Carnosine inhibits the formation of AGEs, thereby potentially mitigating the effects of aging and improving the management of diabetes.

L-Carnosine is abundant in muscle tissues and plays a crucial role in muscle performance and recovery. It acts as a pH buffer, reducing the accumulation of lactic acid during intense physical activity. This buffering capacity enhances muscle endurance and reduces fatigue, which is beneficial for athletes and individuals engaged in strenuous exercise. Supplementing with L-Carnosine can improve exercise performance and accelerate recovery.

L-Carnosine exhibits neuroprotective properties, which are particularly important in the context of neurodegenerative diseases. It has been shown to protect neuronal cells from oxidative damage, excitotoxicity, and the accumulation of harmful proteins. These properties suggest that L-Carnosine could be useful in treating or preventing conditions like Alzheimer's disease and other forms of dementia.

L-Carnosine also promotes wound healing due to its ability to stimulate the production of fibroblasts, the cells responsible for wound repair. Its antioxidant and anti-inflammatory properties further support the healing process by reducing oxidative stress and inflammation at the wound site. This makes L-Carnosine a valuable component in topical formulations for treating wounds and burns.

In the cosmetic industry, L-Carnosine is used in anti-aging skin care products. Its anti-glycation and antioxidant properties help to protect skin cells from damage and maintain skin elasticity and firmness. By preventing the breakdown of collagen and elastin, L-Carnosine helps to reduce the appearance of wrinkles and fine lines, promoting a youthful complexion.

References

1979. Multiple forms of the cobalt(II)-carnosine complex. Biochemical and Biophysical Research Communications, 88(2).
DOI: 10.1016/0006-291x(79)92080-1

1994. L-carnosine (β-alanyl-L-histidine) and carcinine (β-alanylhistamine) act as natural antioxidants with hydroxyl-radical-scavenging and lipid-peroxidase activities. The Biochemical Journal, 304(2).
DOI: 10.1042/bj3040509

2024. Antioxidant/anti-inflammatory xanthan-based hydrogel containing L-Carnosine/Berberine with the potential for periodontal applications. Polymer Bulletin.
DOI: 10.1007/s00289-024-05578-2