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L-Anserine

CAS No.584-85-0
Chemical Name:L-Anserine
CBNumber:CB1875454
Molecular Formula:C10H16N4O3
Formula Weight:240.26
MOL File:584-85-0.mol

L-Anserine Property

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
LogP -2.220 (est)
FDA UNII HDQ4N37UGV

Safety

HS Code :2933299090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H315-H319-H335
Precautionary statements P261-P305+P351+P338

L-Anserine Chemical Properties,Usage,Production

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.
in vivo
Anserine (drinking water at a concentration of 2.0 g/L (equivalent to 10 mg/mouse); for 8 weeks) completely recoveres the memory deficits, improves pericyte coverage on endothelial cells in the brain, and diminishes chronic glial neuroinflammatory reactions in AβPPswe/PSEN1dE9 Alzheimer's disease (AD) model mice over 18-months old^[2].
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