L-Anserine Chemical Properties

Melting point:

268℃ (decomposition)

Boiling point:

611.3±55.0 °C(Predicted)

Density 

1.38±0.1 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

solubility 

Methanol (Slightly, Heated), Water (Slightly)

form 

Solid

pka

3.02±0.10(Predicted)

color 

White to Off-White

InChI

InChI=1/C10H16N4O3/c1-14-6-12-5-7(14)4-8(10(16)17)13-9(15)2-3-11/h5-6,8H,2-4,11H2,1H3,(H,13,15)(H,16,17)/t8-/s3

InChIKey

MYYIAHXIVFADCU-SBYBRXNCNA-N

SMILES

C(C1=CN=CN1C)[C@@H](C(=O)O)NC(=O)CCN |&1:7,r|

LogP

-2.220 (est)

Safety Information

HS Code 

2933299090

L-Anserine Usage And Synthesis

Uses

Anserine, a methylated form of Carnosine, is an orally active, natural Histidine-containing dipeptide found in skeletal muscle of vertebrates. Anserine is not cleaved by serum carnosinase and act as biochemical buffers, chelators, antioxidants, and anti-glycation agents. Anserine improves memory functions in Alzheimer's disease (AD)-model mice[1][2].

Definition

ChEBI: Anserine is a dipeptide comprising of beta-alanine and 3-methyl-L-histidine units. It has a role as an animal metabolite and a mouse metabolite. It is a beta-alanine derivative and a dipeptide. It is a tautomer of an anserine zwitterion.

Synthesis

The general procedure for the synthesis of (S)-2-(3-aminopropionamido)-3-(1-methyl-1H-imidazol-5-yl)propionic acid, using the compound (CAS: 952739-81-0) as a starting material, was as follows: to a solution of methanol (1 mL) containing the ester 14 (18.8 mg, 53.0 μmol), 1 M aqueous sodium hydroxide was added to adjust the pH to >11. The reaction was carried out by stirring the reaction mixture for 16 h at room temperature. reaction mixture was stirred for 16 h at room temperature. Upon completion of the reaction, the solvent was removed by evaporation to give a colloidal residue. This residue was dissolved in distilled water (1 mL) and the reaction mixture was subsequently acidified with 1 M aqueous hydrochloric acid.

in vivo

IC 50

Human Endogenous Metabolite

Purification Methods

Crystallise anserine from aqueous EtOH. It is hygroscopic and is best stored as the nitrate salt (see below). Purify it by shaking the nitrate salt with Dowex 3 (x4 free base) and washing with H2O, evaporating the filtrate and removing H2O by 3 distillations with 10mL of propan-2-ol. Dissolve the crystals in MeOH and add H2O dropwise until one phase is obtained and cool. Dry the crystals at 60o over P2O5 in a vacuum. The picrate has m 145o (from H2O). [Rinderknecht et al. J Org Chem 29 1968 1964, Beilstein 25 II 408, 25 IV 4383.]

References

[1] Boldyrev AA, et al. The histidine-containing dipeptides, carnosine and anserine: distribution, properties and biological significance. Adv Enzyme Regul. 1990;30:175-94. DOI:10.1016/0065-2571(90)90017-v
[2] Jun Kaneko, et al. Anserine (beta-alanyl-3-methyl-L-histidine) improves neurovascular-unit dysfunction and spatial memory in aged AβPPswe/PSEN1dE9 Alzheimer's-model mice. Sci Rep. 2017 Oct 3;7(1):12571. DOI:10.1038/s41598-017-12785-7

L-Anserine(584-85-0)Related Product Information

• Nonathymulin
• Urodilatin (human)
• Secretin (human)
• ATRIAL NATRIURETIC FACTOR (4-28) (HUMAN)
• Secretin
• Palmitoyl tetrapeptide-7
• L-Carnosine
• 3-METHYL-L-HISTIDINE
• L-Anserine
• L-ANSERINE NITRATE