Aspartam

APM · ASPARTAME POWDER · ASPARTAM · ASP-PHE METHYL ESTER · mer · (S)-3-AMino-4-(((S)-1-Methoxy-1-oxo-3-phenylpropan-2-yl)aMino)-4-oxobutanoic acid · Asp-Phe-OMe · Glycopeptide

https://huagongshe.com/de/chemical/134601

Identifikatoren & physikalische Daten

CAS No.	22839-47-0
Summenformel	C14H18N2O5
Durchschnittliche Molmasse	294,3 g/mol
Monoisotopische Masse	294,12157168 g/mol
SMILES	COC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](N)CC(=O)O
InChIKey	IAOZJIPTCAWIRG-QWRGUYRKSA-N
PubChem CID	134601
ChEMBL	CHEMBL171679
ChEBI	CHEBI:2877
EC No.	245-261-3
DTXSID	DTXSID0020107
Lokaler Name	Aspartam

Chemische & physikalische Eigenschaften

XLogP	-2,7
Polarare Oberfläche (TPSA)	119
H-Brücken-Donoren	3
H-Brücken-Akzeptoren	6
Frei drehbare Bindungen	8
Schwere Atome	21
Formalladung	0
Komplexität	380
Stoffklassen	Other Uses -> Food Additives
Arzneimittel	Pharmaceuticals -> Listed in ZINC15
Kosmetika	Masking
pH	Between 4,5 and 6,0 (1 in 125 solution)0.8% Solution in water has a pH of about 5.3.pH(8g/l, 25℃) : 4.5～6.0
Geruch	Odorless
Geschmack	SweetIn the presence of moisture it hydrolyzes to form aspartylphenylalanine and a diketopiperazine derivative, with a resulting loss of sweetness.
Lebensmittelzusatzstoffe	FLAVOR ENHANCER, NON-NUTRITIVE SWEETENER -> FDA Substance added to food
Color/Form	Colorless needles from waterWhite crystalline powder from water or alcohol
Löslichkeit	The solubility of aspartame in water is dependent on pH and temperature, the maximum solubility is reached at pH 2.2 (20 mg/mL at 25 °C) and the minimum solubility at pH 5.2 (pHi) is 13.5 mg/mL at 25 °C.Slightly soluble in water and in ethanolMore soluble in acidic solutions and hot waterslightly soluble in alcoholvery slightly soluble in chloroformpractically insoluble in oils.Solubility in water in mg/mL at 25 °C: 18.2 at pH 3.7216.1 at pH 4.00, 15.2 at pH 4.05, 14.5 at pH 4.27, 13.8 at pH 4.78, 13.5 at pH 5.30, 13.7 at pH 5.70 and 14.2 at pH 6.00in distilled water, 10.20 mg/mL at pH 7.00In water, 1.0X10+4 mg/L at pH 3 and room temperature>44.1 [ug/mL] (The mean of the results at pH 7.4)Sparingly soluble or slightly soluble in water and in ethanol (96 per cent), practically insoluble in hexane and in methylene chloride.Soluble in formic acid, dimethyl sulfoxide. Sparingly soluble in water and ethanol.
Human Drugs	Breast FeedingLactationMilk, HumanArtificial SweetenersSweetening Agents
Animal Drugs	Pharmaceuticals -> UK Veterinary Medicines Directorate List
Decomposition	When heated to decomposition it emits toxic fumes of /nitroxides/.Photodecomposition of aspartame in aqueous solutions under different conditions of light intensity and pH were studied. The effects of photosensitizers (riboflavin and methylene blue) and ascorbic acid on aspartame stability in aqueous solutions at different pH under light were also studied. Light illumination significantly increased aspartame degradation in an aqueous solution (pH 7), indicating that aspartame was very unstable under the illuminated conditions. In the dark, 91% of aspartame in an aqueous solution at pH 7 remained after 10 h of storage. Under 5500 lux of light, however, 39% of aspartame in the solution was destroyed after 10 h of storage. Aspartame degradation under light followed simple zero-order reaction kinetics. The higher the light intensity, the greater the degradation of aspartame. The relative reaction rate for the destruction of aspartame under 0, 1100, 3300 and 5500 lux was 1:1.42:2.80:4.61. The photodecomposition rate of aspartame varied with the pH of the system. Aspartame degradation was fastest at pH 7.0, followed by pH 4.0 and pH 6.0, in decreasing order. Addition of 4.8 ppm riboflavin or 4.8 ppm methylene blue significantly accelerated the aspartame decomposition at pH 7 in the presence of light. There were, however, no significant photosensitizing effects of these sensitizers on aspartame destruction at pH 6 and pH 4. Addition of 1.2x10-4 increased the aspartame degradation at pH 7.0, but did not affect the destruction rate of aspartame at pH 6.0 and pH 4.0.
Schmelzpunkt	242-248 °C
Siedepunkt	436.08°C (rough estimate)
Dichte	1.2051 (rough estimate)
Brechungsindex	14.5 ° (C=4, 15mol/L Formic Acid)
Lagerbedingungen	2-8°C
pKa (Säurekonstante)	pKa 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)
Aggregatzustand	Powder
Farbe	White
Geruch	odorless with a sweet taste
Biologische Quelle	mouse
Merck	14,839
BRN	2223850
Henry-Konstante	3.9×1012 mol/(m3Pa) at 25℃, HSDB (2015)
Stabilität	Stable. Incompatible with strong oxidizing agents.
Kosmetik-Inhaltsstoffe Funktionen	FLAVOURING
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
InChIKey	IAOZJIPTCAWIRG-QWRGUYRKSA-N
SMILES	COC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](N)CC(O)=O
LogP (Verteilungskoeffizient)	0.542 (est)
CAS Datenbank	22839-47-0(CAS DataBase Reference)
EPA chemische Informationen	L-Phenylalanine, L-.alpha.-aspartyl-, 2-methyl ester (22839-47-0)

Sicherheit & Vorschriften

GHS-Einstufung	This chemical does not meet GHS hazard criteria for 96.9% (186 of 192) of all reports.Not ClassifiedAggregated GHS information provided per 192 reports by companies from 4 notifications to the ECHA C&L Inventory.
Regulatorische Informationen	Chemical: L-Phenylalanine, N-L-.alpha.-aspartyl-, 1-methyl esterHazard Traits - CarcinogenicityRegulation (EC) No 1333/2008 (amended)L-Phenylalanine, L-.alpha.-aspartyl-, 2-methyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of L-Phenylalanine, L-.alpha.-aspartyl-, 2-methyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Aspartame: Does not have an individual approval but may be used under an appropriate group standard
Gefahrenübersicht	Causes effects on fluid intake, degenerative changes to brain, and effects on phosphatases and true cholinesterase in acute oral studies of rats[RTECS] An eye and mucous membrane irritant[IUCLID] Acceptable daily intake (ADI) of 0-40 mg/kg[JECFA] May cause irritation[Alfa Aesar MSDS]
FDA-Anforderungen	Aspartame is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity of the substance added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) any substance intended for use in or on food is of appropriate food grade and is prepared and handled as a food ingredient.
Special Reports	WHO Food Additives Series 15. Aspartame. This monograph contains summaries of data on aspartame examined by JECFA in 1975, 1976, 1977 and 1980.[Available from, as of August 3, 2010http://www.inchem.org/documents/jecfa/jecmono/v15je03.htm]WHO Food Additives Series 16. Aspartame. In 1980 JECFA evaluated additional animal studies and several human studies and an ADI of 0-40 mg/kg bw for aspertame and an ADI of 0-7.5 mg/kg bw for its breakdown product, diketopiperazine, were established. Additional studies that have since become available are summarized and discussed in this monograph addendum.[Available from, as of August 3, 2010

Anwendungen & Verwendung

Beschreibung

Aspartame is the most popular artificial sweetener in the United States. It is sold as sweeteners such as NutraSweet and Equal, but it is also incorporated into thousands of food products.

History

Aspartame was discovered accidentally in 1965 during a search for drugs to treat gastric ulcers. James M. Schlatter, an organic chemist working for G. D. Searle & Company, was using aspartyl-phenylalanine methyl ester (aspartame) in a synthesis procedure and inadvertently got some of the compound on his hands.

Verwenden

Aspartame is a high-intensity sweetener that is a dipeptide, provid- ing 4 cal/g. it is synthesized by combining the methyl ester of phenylalanine with aspartic acid, forming the compound n-l-alpha- aspartyl-l-phenylalanine-1-methyl ester. it is approximately 200 times as sweet as sucrose and tastes similar to sugar. it is compara- tively sweeter at low usage levels and at room temperature. its mini- mum solubility is at ph 5.2, its isoelectric point. its maximum solubility is at ph 2.2. it has a solubility of 1% in water at 25°c. the solubility increases with temperature. aspartame has a certain insta- bility in liquid systems which results in a decrease in sweetness. it decomposes to aspartylphenylalanine or to diketropiperazine (dkp) and neither of these forms is sweet. the stability of aspartame is a function of time, temperature, ph, and water activity. maximum stability is at approximately ph 4.3. it is not usually used in baked goods because it breaks down at the high baking temperatures. it contains phenylalanine, which restricts its use for those afflicted with phenylketonuria, the inability to metabolize phenylalanine. uses include cold breakfast cereals, desserts, topping mixes, chew- ing gum, beverages, and frozen desserts. the usage level ranges from 0.01 to 0.02%.

Herstellung & Synthese

synthetische

By coupling the amino acids L-phenylalanine and L-aspartic acid, and the esterification of the carboxyl group of the phenylalanine moiety to produce the methyl ester. This esterification can occur before or after coupling. The crystallized slurry is centrifuged and the resulting “wet-cake” is washed to remove impurities.