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Aspartame
"Descrizione"
by FRanier (9976 pt)
2023-Apr-26 19:03

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Aspartame (L-aspartyl-L-phenylalanine methyl ester) is a chemical compound formed from aspartic acid and phenylalanine.

Industrially it occurs as a fine white powder.



What it is used for and where

Food

The history of aspartame dates back to 1965 when the American chemist and researcher James Schlatter, in an attempt to create a drug against gastric ulcer, chemically derived aspartame in an intermediate step of creating a tetrapeptide of the peptide hormones gastrin.

It is one of the most common sweeteners and on which have been focused countless scientific researches to establish the risks connected to the consumption of this product which is included in many food products: diet drinks, chewing gums, yogurt, desserts, vitamins, medicines. It is recommended to people with diabetes as a substitute of sugar. It has about 200 times the sweetening power of sugar.

In the European Union it is labeled as  E951 in the list of european food additives as a sweetener and it is considered by Efsa (European Food Safety Authority), safe for human health.

The acceptable daily intake of aspartame recommended by the FDA is 50 mg/kg per day in the United States and 40 mg/kg per day in the European Union (EFSA).

Researchers from the Schiller Institute for Integrated Science and Society, Boston, based on the 1997 toxicological studies of the Ramazzini Institute (an independent non-profit research laboratory based in Bologna) carried out on laboratory animals, concluded that aspartame is a chemical carcinogen in rodents even at the dose of 100 mg/kg body weight, a relatively low dose exposure dangerously close to the current permissible daily intake (ADI) levels in the USA and the European Union (1).

High-intensity sweeteners are considered potential organic contaminants due to their widespread use in food, drugs and healthcare products. They are introduced into the environment by different pathways and find their way into water (2).

For more information:

Aspartame studies

Typical optimal characteristics of the commercial product Aspartame

AppearancePowder fine white
Density1.3±0.1 g/cm3
Alpha15.5 º (c=4, 15N formic acid)
Melting Point242-248 °C
Boiling Point535.8±50.0 °C at 760 mmHg
Flash Point277.8±30.1 °C
14.5 ° (C=4, 15mol/L Formic Acid)
Vapour Pressure0.0±1.5 mmHg at 25°C
Storage2-8°C
Solubility

Sparingly soluble or slightly soluble in water and in ethanol (96 per cent), practically insoluble in hexane and in methylene chloride.

PkapKa 3.19±0.01 (H2O t=25.0 I=0.100(NaCl))(Approximate);7.87±0.02(H2O t=25.0 I=0.100(NaCl))(Approximate)


  • Molecular Formula: C14H18N2O5
  • Linear Formula:HOOCCH2CH(NH2)CONHCH(CH2C6H5)COOCH3
  • Molecular Weight: 294.307 g/mol
  • CAS: 22839-47-0  7421-84-3
  • EC Number: 245-261-3  616-062-2
  • UNIII: Z0H242BBR1
  • Beilstein Registry Number:2223850
  • MDL number: MFCD00002724
  • PubChem Substance ID 24870725
  • InChI=1S/C14H18N2O5/c1-21-14(20)11(7-9-5-3-2-4-6-9)16-13(19)10(15)8-12(17)18/h2-6,10-11H,7-8,15H2,1H3,(H,16,19)(H,17,18)/t10-,11-/m0/s1 
  • InChl Key    IAOZJIPTCAWIRG-QWRGUYRKSA-N  
  • SMILES    COC(=O)C(CC1=CC=CC=C1)NC(=O)C(CC(=O)O)N
  • IUPAC   (3S)-3-amino-4-[[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid
  • ChEBI    2877

Synonyms:

  • Nutrasweet
  • L-Aspartyl-L-phenylalanine methyl ester
  • Asp-phe-ome
  • Aspartylphenylalanine methyl ester
  • Asp-Phe methyl ester
  • Methyl aspartylphenylalanate
  • Aspartam
  • Dipeptide sweetener
  • Aspartamum
  • 1-Methyl N-L-alpha-aspartyl-L-phenylalanate
  • Aspartamo
  • 3-amino-3-[(1-methoxycarbonyl-2-phenyl-ethyl)carbamoyl]propanoic acid

References_____________________________________________________________________

(1) Landrigan PJ, Straif K. Aspartame and cancer - new evidence for causation. Environ Health. 2021 Apr 12;20(1):42. doi: 10.1186/s12940-021-00725-y. 

(2) Arbeláez P, Borrull F, Pocurull E, Marcé RM. Determination of high-intensity sweeteners in river water and wastewater by solid-phase extraction and liquid chromatography-tandem mass spectrometry. J Chromatogr A. 2015 May 8;1393:106-14. doi: 10.1016/j.chroma.2015.03.035. 

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