AMINOACETONE HYDROCHLORIDE Chemical Properties

Melting point:

73-74 °C

storage temp. 

Inert atmosphere,2-8°C

solubility 

DMF: 25 mg/ml; DMSO: 15 mg/ml; Ethanol: 10 mg/ml; PBS (pH 7.2): 10 mg/ml

form 

A crystalline solid

color 

Off-white to yellow

Stability:

Hygroscopic

InChI

InChI=1S/C3H7NO.ClH/c1-3(5)2-4;/h2,4H2,1H3;1H

InChIKey

RUCLDQBBIJKQHO-UHFFFAOYSA-N

SMILES

C(=O)(C)CN.Cl

AMINOACETONE HYDROCHLORIDE Usage And Synthesis

Description

Aminoacetone is a threonine and glycine catabolite that can be converted to methylglyoxal by amine oxidases. It has been identified as one of several endogenous sources of methylglyoxal found in the plasma of diabetes patients. As a pro-oxidant, 0.10-5 mM aminoacetone can induce cell death in RINm5f pancreatic β-cells. Aminoacetone is used as a growth substrate for Pseudomonas.

Chemical Properties

White to Off-White Solid

Uses

Aminoacetone hydrochloride is the simplest monopeptide. Aminoacetone hydrochloride is an intermediate in the metabolism of threonine and glycine. Aminoacetone hydrochloride is an endogenous substrate for semicarbazide-sensitive amine oxidase (SSAO), and can be used for determination of SSAO activity[1].

Synthesis

1-Benzyloxycarbonylamino-2-propanone (3) (8.6 g, 42 mmol) was used as a raw material, which was dissolved in ethanol (50 mL) and 1N hydrochloric acid solution (46 mL) was added. The reaction was stirred in the presence of Pd/C catalyst (1.5 g, 10%) for 4 h at room temperature in a hydrogen atmosphere (1 atm). Upon completion of the reaction, the reaction mixture was filtered to remove the catalyst and the filtrate was concentrated. The resulting residue was ground with ether (Et2O) to give 1-amino-2-propanone hydrochloride (4.6 g, 100%) as a white solid.1H NMR (CD3OD) data: δ 3.92 (s, 2H), 2.12 (s, 3H).

References

[1] Deng Y, et al. Assessment of the deamination of aminoacetone, an endogenous substrate for semicarbazide-sensitive amine oxidase. Anal Biochem. 1999 May 15;270(1):97-102. DOI:10.1006/abio.1999.4058

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