| Identification | Back Directory | [Name]
L-Anserine | [CAS]
584-85-0 | [Synonyms]
Anserin
L-Anserine
H-β-Ala-His(3-Me)-OH
L-Histidine, β-alanyl-3-methyl-
beta-Alanyl-3-methyl-L-histidine
L-N-beta-Alanyl-3-methylhistidine
N-beta-alanyl-3-methyl-L-histidine
Nα-β-Alanyl-1-dehydro-3-methyl-L-histidine
2-(3-aminopropanoylamino)-3-(3-methylimidazol-4-yl)-propanoic acid
(S)-2-(4-Aminobutanamido)-3-(1-methyl-1H-imidazol-5-yl)propanoic acid
(S)-2-(3-Aminopropanamido)-3-(1-methyl-1H-imidazol-4-yl)propanoic acid
(S)-2-(3-Aminopropanamido)-3-(1-methyl-1H-imidazol-5-yl)propanoic acid
(2S)-2-[(3-ammonio-1-oxopropyl)amino]-3-(3-methyl-4-imidazolyl)propanoate | [EINECS(EC#)]
209-545-0 | [Molecular Formula]
C10H16N4O3 | [MDL Number]
MFCD11040910 | [MOL File]
584-85-0.mol | [Molecular Weight]
240.26 |
| Chemical Properties | Back Directory | [Melting point ]
268℃ (decomposition) | [Boiling point ]
611.3±55.0 °C(Predicted) | [density ]
1.38±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,2-8°C | [solubility ]
Methanol (Slightly, Heated), Water (Slightly) | [form ]
Solid | [pka]
3.02±0.10(Predicted) | [color ]
White to Off-White | [Cosmetics Ingredients Functions]
ANTIOXIDANT
HUMECTANT
SKIN CONDITIONING | [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) |
| Hazard Information | Back Directory | [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]
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 | [storage]
Store at 4°C, protect from light | [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 |
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