N-beta-alanyl-L-histidine

Base Information

• Chemical Name: N-beta-alanyl-L-histidine
• CAS No.: 305-84-0
• Molecular Formula: C9H14N4O3
• Molecular Weight: 226.235
• Hs Code.: 29332900
• Mol file: 305-84-0.mol

Synonyms:N-beta-alanyl-L-histidine;carnosine zwitterion;CHEBI:57485;N(alpha)-(beta-alaniniumyl)-L-histidinate;(2S)-2-[(3-azaniumylpropanoyl)amino]-3-(1H-imidazol-4-yl)propanoate

Chemical Property of N-beta-alanyl-L-histidine

Chemical Property:

• Appearance/Colour: crystalline
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 253 °C (dec.)(lit.)
• Refractive Index: 21 ° (C=2, H2O)
• Boiling Point: 511.7 °C at 760 mmHg
• PKA: 2.62(at 25℃)
• Flash Point: 263.3 °C
• PSA: 121.10000
• Density: 1.41 g/cm³
• LogP: -0.03840
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Very Slightly), Water (Slightly)
• Water Solubility.: almost transparency
• XLogP3: -3.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 226.10659032
• Heavy Atom Count: 16
• Complexity: 254

Purity/Quality:

99%, ^*data from raw suppliers

Carnosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(NC=N1)CC(C(=O)[O-])NC(=O)CC[NH3+]
• Isomeric SMILES: C1=C(NC=N1)C[C@@H](C(=O)[O-])NC(=O)CC[NH3+]
• Chemical Composition and Structure: Carnosine, also known as β-alanyl-L-histidine, is a dipeptide composed of the amino acids β-alanine and L-histidine. It is characterized by its low molecular weight and hydrophilic nature.
• Sources: Carnosine is found endogenously in body tissues, particularly in skeletal muscle, where its concentration is higher than in any other tissue. It is also present in other excitable tissues.; Carnosine can be synthesized in the body when histidine and β-alanine are combined in the presence of carnosine synthase. It can also be obtained from dietary sources or produced through chemical synthesis for use in supplements and pharmaceuticals.
• Uses: Mechanism of Action:; Carnosine exhibits various functional and biological properties, primarily as an antioxidant. It can chelate metal ions and scavenge reactive oxygen species (ROS), thereby reducing oxidative stress. Additionally, it influences glycemic control, prevents diabetic-associated complications, and has a protective effect on telomere shortening, contributing to its anti-aging properties.; Uses in Medical Applications:; Carnosine has been investigated for its therapeutic potential in various diseases involving ischemic or oxidative stress, such as diabetes, ocular disease, aging-related disorders, and neurological conditions. It has shown promising results in preclinical and clinical studies.

Technology Process of N-beta-alanyl-L-histidine

There total 40 articles about N-beta-alanyl-L-histidine 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: 94.5%

C9H12ClN3O3 → Carnosine (305-84-0)

Guidance literature:

With ammonium bicarbonate; at 60 ℃; for 24h;

Reference yield: 92.3%

N-benzyloxycarbonyl-beta-alanyl-L-histidine hydrochloride → Carnosine (305-84-0)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In methanol; water; for 24h; under 760.051 Torr;

Reference yield: 90.0%

3-(tert-butyloxycarbonylamino)propionic acid (3303-84-2) + N-9-fluorenylmethyloxycarbonyl-N-trityl-L-histidine → carnosine (305-84-0)

Guidance literature:

N-9-fluorenylmethyloxycarbonyl-N-trityl-L-histidine; With trityl chloride polystyrene resin; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; for 0.5h; trityl chloride resin

With piperazine; In dichloromethane; N,N-dimethyl-formamide; for 1h; trityl chloride resin Inert atmosphere;

3-(tert-butyloxycarbonylamino)propionic acid; Further stages;

DOI:10.5935/0103-5053.20160064

upstream raw materials:

N^α-(N,N-phthaloyl-β-alanyl)-histidine

3-iodopropionyl chloride

L-histidine

3-amino propanoic acid

Downstream raw materials:

D,L-histidine

3-amino propanoic acid

4-toluenesulfonylureido-carnosine

N-(4-n-tetradecyloxybenzoyl)-L-carnosine

Refernces

• 1、 Vinick,Jung. "A simple and efficient synthesis of l-carnosine". . p. 392 - 393. Retrieved 1983.
• 2、 WINNICK,WINNICK. "Carnosineanserine synthetase of muscle. I. Preparation and properties of soluble enzyme from chick muscle.". . p. 47 - 55. Retrieved 1959.
• 3、 -. "Carnosine intermediate and preparation and application of carnosine thereof". Paragraph 0039; 0040. . Retrieved 2022/03/27.
• 4、 Yin, Dong-Ya,Pan, Jiang,Zhu, Jie,Liu, You-Yan,Xu, Jian-He. "A green-by-design bioprocess for l-carnosine production integrating enzymatic synthesis with membrane separation". . p. 5971 - 5978. Retrieved 2019/11/14.