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22839-47-0

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  • 2023 New Date Stevia Aspartame Sucralose Neotame Saccharin CAS 22839-47-0 Aspartame powder sweetener

    Cas No: 22839-47-0

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22839-47-0 Usage

Artificial sweeteners

Aspartame is a kind of artificial sweeteners, belongs to the amino acid dipeptide derivatives, by the chemist developed ulcer drugs found in 1965. With low dosage, high sweetness (sweetness is 150 to 200 times of sucrose), good taste, enhance flavor of citrus and other fruits and reducing heat does not produce dental caries, toxicity than saccharin and other synthetic sweetening agent advantages, is widely applied to beverages, diabetic food and some slimming health food, our daily life to drink cola formula once containing the product. Aspartame in the metabolic processes in the body and the main degradation products are phenylalanine, methanol and aspartic acid, does not enter blood circulation, and does not accumulate in the body, food for the health harmless. But due to metabolic defects in patients with phenylketonuria (PKU), excessive body phenylalanine can influence its development, so in patients with the disease to disable adding aspartame.

Neotame

Neotame is aspartate dipeptide derivatives, is a new product developed at a cost of $80 million by American newt company after aspartame, representing the latest achievements of sweetener research field. It is according to the human sweet receptor double hydrophobic binding hypothesis. In aspartame molecule with a hydrophobic groups and the formation of aspartame derivatives. It can also act on the human sweet receptor of two hydrophobic binding sites and therefore sweetness increased greatly, 6000 to 10000 times sweeter than sucrose, 30 to 60 times than Biasiba sweet . It retains many excellent characteristics such as aspartame, pure sweet taste and good flavor enhancing properties distribution, no energy, no caries, stable in acidic medium. Moreover, it is still a lot better than aspartame in dry conditions, it has a longer shelf life; in neutral medium or instantaneous high temperature sterilization conditions, its stability greatly exceed aspartame, which can be used as a sweetener in baking. Neotame can also be used together with reducing sugar and aldehyde flavor without adverse reaction, its safety is better than aspartame and has been greatly improved. Due to its high sweetness, etc. Sweeter is lower than the cost of aspartame. Therefore, neotame has huge market potential. In December of 1998, neotame as food sweeteners status of application have been proposed in the United States, and some other countries for the certification work is in July 9, 2002 . The U. S. Food and Drug Administration (FDA) confirmed the neotame safety and functional type, currently is in March 10, worldwide more regulatory agency and national review in 2003, China's Ministry of Health approval for neotame as a sweetener used in all kinds of food. The above information is edited by the lookchem Han Ya.

Content analysis

Accurately take sample of about 300 mg, moves into a 150ml beaker, dissolve in 96% formic acid 1.5ml, and glacial acetic 60ml. with crystal violet solution (ts-74), with 0.1 mol/L HClO4 immediately titrate to the end of green. At the same time a blank titration and make necessary correction. Each mI.0.1mol/L perchloric acid is the equivalent of 29.43mg C14H18N2O5.

Toxicity

Entering the human body can quickly metabolic day aspartic acid and phenylalanine, two kinds of amino acids are absorbed, which does not accumulate in the organization. But phenylketonuria patients cannot use. Therefore it is necessary to specially marked. Every year in China about 1500~2000 benzene acetone urine disease in children born, after eating can be in vivo abnormal accumulation caused by brain damage, mental development retardation and epilepsy. The ADI value is 0~40mg/kg (FAO/WHO, 2001). Contains two ketone piperazine ADI value is 0~7.5. GRAS (FDA, 172.804,2000).

Use limits

GB 2760-2001: all types of food (except canned food), are limited to GMP. FAO/WHO (1984): sweets 0.3%, gum 1.0%; beverage 0.1%, 0.5% of breakfast cereals, and used for the preparation of diabetes, hypertension, obesity, cardiovascular patients with low sugar, low calorie health food, dosage depends on the need to set. Can also be used as flavor enhancer.

chemical property

White crystalline powder, odorless, there is strong sweet, sweet and pure, sweetness of sucrose was 100-200 times. Melting point is 235℃ (decomposition). Amino acids is with the general nature. In dry conditions or pH value of 2 to 5 range, it is stability, strong acidic water solution can hydrolyzed to produce amino acid monomer, in neutral or alkaline conditions it can be cyclized to diketopiperazine. Solubility in water (25℃) is relevant to pH value, pH 7.0 was 10.2%, pH value 3.72 is 18.2%. At 25, isoelectric point is pH value of 5.2. Mice by oral LD50 > 10 g/kg Adl is 0~40mg/kg (FAO/who, 1994)

Uses

Different sources of media describe the Uses of 22839-47-0 differently. You can refer to the following data:
1. 1.Asparagus sweet is artificial synthesis of low calorie sweeteners, often used with sugar or other sweeteners. It can be used for all kinds of food, according to the production need to use, the general dosage is 0.5g/kg. 2.It Is used as a food additive, high sweetness nutritive sweeteners. 3.Non nutritive sweeteners. Flavoring agents. 4.According to China GB2760-90 provisions for all kinds of food, the maximum amount of use as normal production needs. According to the FAO/WHO (1984) provisions for sweets, dosage of 0.3%, 1.0% gum, beverage 0.1%, 0.5% of breakfast cereals, and used for the preparation of diabetes, hypertension, obesity, cardiovascular patients with low sugar, low calorie health food, dosage depends on the need to set. Can also be used as a flavor enhancer. Aspartame is a L-aspartic acid and L-phenylalanine (body needed nutrients) two peptide synthesis, can be completely absorbed by the human body metabolism, non-toxic harmless, safe and reliable, cool and refreshing taste like sugar, but is 200 times sweeter than sucrose, the heat is only 1/200 sucrose, eat no gingivae that does not affect the blood glucose, obesity, hypertension, coronary heart disease. The World Health Organization (WHO) and the United Nations Food and Agriculture Organization (FAO) identified as A (1) level of sweetener, has been in the world more than 130 countries and regions approved for use. Widely added in a variety of food, non-staple food and all kinds of hard and soft drinks, the use of aspartame has more than 4000 kinds of varieties. Can be used as food additives, high sweetness sweeteners with nutrition. Packing: 25 kg fibreboard drum, lined with plastic bag.
2. Aspartame in powder form for limited uses such as cereals, powdered drinks, and chewing gum. When aspartame is used in baked goods and baking mixes, it should not exceed 0.5% by weight. Packages of the dry, free-fl owing aspartame are required to prominently display the sweetening equivalence in teaspoons of sugar.
3. A dipeptide ester about 160 times sweeter than sucrose in aqueous solution. A non-nutritive sweetener.
4. 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%.
5. The chemical name for aspartame is L-aspartyl-L-phenylalamine methyl ester. It is a white crystalline powder and is about 200 times as sweet as sucrose. It is noted for a clean, sweet taste that is similar to that of sucrose. Aspartame is the most widely used artificial sweetener in the world. It was approved by the FDA for use in the USA in 1981, and now is approved for use in several other countries of the world. One of the drawbacks of aspartame is its instability to heat and acid. Under acidic conditions aspartame slowly hydrolyzes leading to a loss of sweetness, chemical interaction, and microbial degradation. The shelf life of the aspartame-sweetened products with high water content is limited to about 6 months, after which it breaks down into its constituent components and loses its sweetening abilities. At elevated temperatures, solid aspartame slowly releases methanol to form aspartyl phenylalamine and the dioxopiperazine. This reaction is especially favored at neutral and alkaline pH values. Because of this reason, aspartame cannot be used in hot baking foods. Another disadvantage of aspartame was noticed in the human digestive system. When the body ingests aspartame, it breaks down into its three constituent components: phenylalamine, aspartate, and methanol. The phenylalamine and aspartate are handled by enzymes in the stomach and in the small intestine, while the methanol is transported to the liver for detoxification. The metabolism of phenylalamine requires an enzyme that is not produced by a small proportion of the population having a genetic disorder called phenyl keton uria (PKU). Aspartame should be avoided by persons suffering from PKU. A warning to PKU sufferers on aspartame-containing products is required in many countries.

Methods of production

1. By L-aspartate and L-phenylalanine methyl ester condensation. 2. By L-aspartic acid and L-phenylalanine methyl ester hydrochloride condensation. There are two kinds of synthetic and enzymatic synthesis. enzymic synthesis : Department of chemistry, Wuhan University, Tao Guoliang, gave the following synthetic route: The preparation of I : 0.5mmol benzyloxy carbonyl aspartic acid, 1.5mmol phenylalanine methyl ester hydrochloride and 2.5ml water were added to 25 ml Erlenmeyer flask, with ammonia to adjust the pH to 6, adding 7mg of thermophilic protease, at 40℃mixing reaction for 6h. Filter and washed with distilled water, and drying to obtain white solid (I) 0.29g, 95.6% yield, melting point is 116 to 118 ℃. Elemental analysis results: C 62.96%, H6.09%.N of 6.65%. preparation of II: it will be joined the conical flasks 0.5g sample I and 20mL3mol/L hydrochloride 25ml and 45℃ in the mixing reaction for 0.5h. Filtration and washing with distilled water, drying to obtain 0.32g the product II, yield is 92%, melting point is 129 to 131℃. Elemental analysis results: C 61.45%, H 5.42% , N 6.82%. Preparation of III will 0.2g palladium carbon catalyst (10%), 20 ml of glacial acetic acid, 5 ml of water add 100 ml three necked flask, hydrogenation activation 1.5h. Join 0.6g II 20 ml acetic acid dissolution and, at 30℃ stirring hydrogenated after 6h. the reaction is completed after filtration, catalyst with acetic acid washing 3 times; the filtrate and washings were concentrated under reduced pressure to dry, 15ml of benzene, continue to decompress and concentrate to dry white solid, and drying to obtain 0.38g the product III, and the yield was 92.3%, the melting point is 245 ℃. The elemental analysis results: C 55.63%, H6.23%, N 8.96%. Chemical synthesis method The aspartic acid and phenylalanine as raw material, by amino protection, anhydride, condensation, hydrolysis, neutralization and other steps of the synthesis. Different protecting groups, different methylated sequence can have a variety of different synthesis methods. Such as the use of formyl as protecting groups and after methyl esterification process route.Into a 250ml flask into 27mL 95% of the methanol and 0.2g oxidation of magnesium and magnesium oxide is dissolved, add 100ml 98% of acetic anhydride, at this time, the temperature gradually rose to 40 ℃, adding acid 67gL-aspartic, heated to 50℃, stirring reaction time 2.5h insulation and fill with 15mL98% acetic anhydride, temperature and reaction time 2.5h, join 16ml isopropanol and continue for 1.5h, the reaction after cooling to room temperature. Put the inner anhydride materialized to join 1000ml flask, add 207mL ethyl acetate and 66Gl-phenylalanine, stirring 1.5h in 25 to 30℃, add the glacial acetic acid 126mL, continue to reflect 4.5h, the reaction after the end of the vacuum to remove the solvent and to the temperature of the reaction system 65℃ so far. Then add 35% hydrochloric acid methylmercury, heating to 60 ℃, return at the end of the reaction of the hydrolysis of 2h, atmospheric distillation until boiling temperature of 63℃ (reaction temperature of 73 degrees C) so far, adding methanol 180, to continue the distillation to the system temperature of 85 ℃ so far. After cooled to 25℃, the removal of the vacuum light group. Adding 35% hydrochloric acid 54mL to the hydrolysis liquid, methanol 9mL and water 43mL. In 20 to 30℃for esterification reaction was then filtered, washed separation from α-APM hydrochloride. It dissolves in 600ml distilled water, to 40 to 50 ℃ of 5%~10% NaOH solution and to Ph=4.5. cooling below, filtering, washing to α-APM crude product, and then dissolved in 500 ml of methanol and water (volume ratio of 1:2) mixture. The cooling crystallization, filtration washing, vacuum drying 45% yield in terms of L-phenylalanine. The Japanese scholars put forward a route without protection: 90g phenylalanine methyl ester hydrochloride is dissolved in 450mL water, 24g sodium carbonate neutralization, two vinyl chloride extraction and 2350mL obtained. Adding 9g phenylalanine methyl ester of acetic acid and methanol extracts 8mL, 15.2g aspartic anhydride hydrochloride added at-20 deg.c, stirring for 30min, hot water and sodium carbonate were added to 70~80 350mL C (5.7g) 300mL. solution with 150mL two vinyl chloride 2 remaining after extraction of phenylalanine methyl ester, water with dilute hydrochloric acid to adjust the Ph value to the 4.8. of the aqueous solution of paper electrophoresis measured with 18.2G (molar yield of 60%) and 6.1g (α-APM beta 20% molar yield) β--APM. This solution is vacuum concentration 100mL, plus.36% hydrochloric acid 30mL, set the refrigerator overnight. A-APM-HCl 21.3g Precipitation Crystallization (yield 58%), the crystallization of filtered and dissolved in 200mL water solution. Stirring at 50 ℃, with 5% sodium carbonate solution to adjust the Ph value to 4.8, and then place the refrigerator overnight in the analysis And filtering to obtain alpha APM crystallization) (43% yield). Crystal dissolved in 500ml water. In 45℃ by Dowex 1 x 4 (acetate) columns (1 x 20cm), and 20 ml of water flushing, effluent and washings together vacuum concentration, precipitation of alpha APM crystallization 11.2g. yield of 37%, melting point 235~236℃ (decomposition), than the rotation alpha D22 32.0 ℃ = 1, Cu Suanzhong. Elemental analysis results: 55.30% C, H 6.19%, n 9.36%.

Category

Toxic substances

Explosive hazard characteristics

Edible contact dermatitis.

Combustible hazard characteristics

Combustible; combustion produces toxic nitrogen oxide smoke

Storage and transportation characteristics

Combustible; combustion produces toxic nitrogen oxide smoke

Fire extinguishing agent

Dry powder, foam, sand, carbon dioxide, mist water

Description

Different sources of media describe the Description of 22839-47-0 differently. You can refer to the following data:
1. Aspartame is a synthetic non-caloric sweetener that is metabolized to phenylalanine, aspartic acid, and methanol in the gut. Aspartame (80 mg/kg per day for 90 days) increases plasma alanine aminotransferase (ALT) and aspartate aminotransferase (AST) activity, induces hepatocyte degeneration and leukocyte infiltration in the liver, and reduces hepatic levels of reduced glutathione (GSH), oxidized glutathione (GSSG), and γ-glutamylcysteine (γ-GC) in mice. Formulations containing aspartame have been used as sweetening agents and flavor enhancers in foods and beverages.
2. 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.

Chemical Properties

Different sources of media describe the Chemical Properties of 22839-47-0 differently. You can refer to the following data:
1. Aspartame has no odor, but has an intense sweet taste. It is a high intensity sweetener, about 160 to 200 times sweeter than sucrose. Normal digestive processes convert aspartame to phenylalanine, aspartic acid and methanol. Metabolism of aspartame in the body provides approximately 17 kJ (4 kcal)/g. The stability of aspartame is affected by moisture, pH and temperature. For a detailed description of this compound, refer to Burdock (1997).
2. white powder or tablets
3. Aspartame (N-L-aspartyl-L-phenylalanine-1-methyl ester, 3-amino-N-(a-carbomethoxy- phenethyl)-succinamic acid-N-methyl ester) is an intense sweetener widely used in foods and beverages. Its solubility in water is approximately 10 g/L at room temperature. Aspartame is not fully stable under common processing and storage conditions of foods and beverages with the highest stability around pH 4.3. Aspartame is about 200 times sweeter than sucrose with a clean, but slightly lingering sweetness. It is used as the single sweetener, but often also in blends with other intense sweeteners owing to synergistic taste enhancement and taste quality improvement often seen in such blends. In the European Union, aspartame is approved as E 951 for a large number of food applications. In the United States, it is approved as a multipurpose sweetener for food and beverage uses and it is also approved in many other countries.
4. Aspartame occurs as an off white, almost odorless crystalline powder with an intensely sweet taste.

Originator

Canderel,Searle,France,1979

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.

Definition

ChEBI: A dipeptide composed of methyl L-phenylalaninate and L-aspartic acid joined by a peptide linkage.

Preparation

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.

Production Methods

Different sources of media describe the Production Methods of 22839-47-0 differently. You can refer to the following data:
1. Aspartame is synthesized using the L enantiomer of phenylalanine. The L enantiomer is separated from the D enantiomer, the racemic mixture, by reacting it with acetic anhydride (CH32
2. Aspartame is produced by coupling together L-phenylalanine (or Lphenylalanine methyl ester) and L-aspartic acid, either chemically or enzymatically. The former procedure yields both the sweet aaspartame and nonsweet β-aspartame from which the α-aspartame has to be separated and purified. The enzymatic process yields only α-aspartame.

Manufacturing Process

A solution of 88.5 parts of L-phenylalanine methyl ester hydrochloride in 100 parts of water is neutralized by the addition of dilute aqueous potassium bicarbonate, then is extracted with approximately 900 parts of ethyl acetate. The resulting organic solution is washed with water and dried over anhydrous magnesium sulfate. To that solution is then added 200 parts of Nbenzyloxycarbonyl- L-aspartic acid α-p-nitrophenyl, β-benzyl diester, and that reaction mixture is kept at room temperature for about 24 hours, then at approximately 65°C for about 24 hours. The reaction mixture is cooled to room temperature, diluted with approximately 390 parts of cyclohexane, then cooled to approximately -18°C in order to complete crystallization. The resulting crystalline product is isolated by filtration and dried to afford β- benzyl N-benzyloxycarbonyl-L-aspartyl-L-phenylalanine methyl ester, melting at about 118.5-119.5°C. To a solution of 180 parts of β-benzyl N-benzyloxycarbonyl-L-aspartyl-Lphenylalanine methyl ester in 3,000 parts by volume of 75% acetic acid is added 18 parts of palladium black metal catalyst, and the resulting mixture is shaken with hydrogen at atmospheric pressure and room temperature for about 12 hours. The catalyst is removed by filtration, and the solvent is distilled under reduced pressure to afford a solid residue, which is purified by recrystallization from aqueous ethanol to yield L-aspartyl-L-phenylalanine methyl ester. It displays a double melting point at about 190°C and 245- 247°C.

Therapeutic Function

Sugar supplement

Biotechnological Production

Aspartame is produced from L-aspartic acid and L-phenylalanine and methanol or alternatively L-phenylalanine methyl ester. The standard process uses common chemical methods of peptide synthesis. Enzymatic coupling of the two amino acids is also possible. N-formyl-L-aspartic acid and L- or D.L-phenylalanine methyl ester can be condensed to aspartame by thermolysin-like proteases. The formylated aspartame can be deformylated chemically or with a formylmethionyl peptide deformylase to yield the sweetener.The enzymatic coupling does not require L-phenylalanine but can start from the racemic product obtained in chemical synthesis, and the remaining D-phenylalanine can be racemized again. Production processes based on fermentation are available for the two main components, aspartic acid and phenylalanine.

General Description

Asp-Phe methyl ester (aspartame, APM, ASP), a dipeptide ester, is made up of phenyl alanine and aspartic acid. Its genotoxic effects have been investigated. Its interaction with certain hydrocolloids has been studied.

Pharmaceutical Applications

Aspartame is used as an intense sweetening agent in beverage products, food products, and table-top sweeteners, and in pharmaceutical preparations including tablets, powder mixes, and vitamin preparations. It enhances flavor systems and can be used to mask some unpleasant taste characteristics; the approximate sweetening power is 180–200 times that of sucrose. Unlike some other intense sweeteners, aspartame is metabolized in the body and consequently has some nutritive value: 1 g provides approximately 17 kJ (4 kcal). However, in practice, the small quantity of aspartame consumed provides a minimal nutritive effect.

Biochem/physiol Actions

Asp-Phe methyl ester (Asp-Phe-OMe) is used as a synthetic sweeter, sugar substitute. Asp-Phe methyl ester is being studied for a variety of potential benefits as a nutrition supplement, such as the delay of osteoarthritis and modulation of rheumatoid factor activity. Asp-Phe methyl ester is being studied for its effect on thrombin activity and blood clotting.

Safety Profile

Human systemic effects byingestion: allergic dermatitis. Experimental reproductiveeffects. When heated to decomposition it emits toxicfumes of NOx.

Safety

Aspartame is widely used in oral pharmaceutical formulations, beverages, and food products as an intense sweetener, and is generally regarded as a nontoxic material. However, the use of aspartame has been of some concern owing to the formation of the potentially toxic metabolites methanol, aspartic acid, and phenylalanine. Of these materials, only phenylalanine is produced in sufficient quantities, at normal aspartame intake levels, to cause concern. In the normal healthy individual any phenylalanine produced is harmless; however, it is recommended that aspartame be avoided or its intake restricted by those persons with phenylketonuria. The WHO has set an acceptable daily intake for aspartame at up to 40 mg/kg body-weight. Additionally, the acceptable daily intake of diketopiperazine (an impurity found in aspartame) has been set by the WHO at up to 7.5 mg/kg body-weight. A number of adverse effects have been reported following the consumption of aspartame, particularly in individuals who drink large quantities (up to 8 liters per day in one case) of aspartame-sweetened beverages. Reported adverse effects include: headaches; grand mal seizure;memory loss;gastrointestinal symptoms; and dermatological symptoms. However, scientifically controlled peer-reviewed studies have consistently failed to produce evidence of a causal effect between aspartame consumption and adverse health events. Controlled and thorough studies have confirmed aspartame’s safety and found no credible link between consumption of aspartame at levels found in the human diet and conditions related to the nervous system and behavior, nor any other symptom or illness. Aspartame is well documented to be nongenotoxic and there is no credible evidence that aspartame is carcinogenic. Although aspartame has been reported to cause hyperactivity and behavioral problems in children, a double-blind controlled trial of 48 preschool-age children fed diets containing a daily intake of 38 ± 13 mg/kg body-weight of aspartame for 3 weeks showed no adverse effects attributable to aspartame, or dietary sucrose, on children’s behavior or cognitive function.

Environmental Fate

Aspartame is nontoxic. However, individuals with the rare, genetic disease, phenylketonuria (PKU), cannot properly metabolize phenylalanine. Such individuals are detected by testing at birth and placed on special low-phenylalanine diets to control their blood phenylalanine concentrations. Thus, PKU individuals need to be aware that aspartame is a source of phenylalanine.

Metabolic pathway

The rate of aspartame degradation is faster in a phosphate buffer solution than in a citrate buffer solution at the same pH and buffer concentration. The primary mechanism by which aspartame degrades, the formation of diketo piperazine, involves the nucleophilic attack of carbonyl by the free amine, which requires proton transfer.

storage

Aspartame is stable in dry conditions. In the presence of moisture, hydrolysis occurs to form the degradation products L -aspartyl-Lphenylalanine and 3-benzyl-6-carboxymethyl-2,5-diketopiperazine with a resulting loss of sweetness. A third-degradation product is also known, β-L-aspartyl-L-phenylalanine methyl ester. For the stability profile at 258℃ in aqueous buffers. Stability in aqueous solutions has been enhanced by the addition of cyclodextrins, and by the addition of polyethylene glycol 400 at pH 2. However, at pH 3.5–4.5 stability is not enhanced by the replacement of water with organic solvents. Aspartame degradation also occurs during prolonged heat treatment; losses of aspartame may be minimized by using processes that employ high temperatures for a short time followed by rapid cooling. The bulk material should be stored in a well-closed container, in a cool, dry place.

Incompatibilities

Differential scanning calorimetry experiments with some directly compressible tablet excipients suggests that aspartame is incompatible with dibasic calcium phosphate and also with the lubricant magnesium stearate. Reactions between aspartame and sugar alcohols are also known.

Regulatory Status

Accepted for use as a food additive in Europe and in the USA. Included in the FDA Inactive Ingredients Database (oral powder for reconstitution, buccal patch, granules, syrups, and tablets). Included in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

Check Digit Verification of cas no

The CAS Registry Mumber 22839-47-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,8,3 and 9 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 22839-47:
(7*2)+(6*2)+(5*8)+(4*3)+(3*9)+(2*4)+(1*7)=120
120 % 10 = 0
So 22839-47-0 is a valid CAS Registry Number.
InChI:InChI=1/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

22839-47-0 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (A0997)  Aspartame  >98.0%(HPLC)(T)

  • 22839-47-0

  • 1g

  • 360.00CNY

  • Detail
  • TCI America

  • (A0997)  Aspartame  >98.0%(HPLC)(T)

  • 22839-47-0

  • 25g

  • 1,270.00CNY

  • Detail
  • Supelco

  • (47135)  Aspartame  analytical standard

  • 22839-47-0

  • 000000000000047135

  • 288.99CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1381)  Aspartame  pharmaceutical secondary standard; traceable to USP, PhEur

  • 22839-47-0

  • PHR1381-1G

  • 718.73CNY

  • Detail
  • Sigma-Aldrich

  • (A1320000)  Aspartame  European Pharmacopoeia (EP) Reference Standard

  • 22839-47-0

  • A1320000

  • 1,880.19CNY

  • Detail
  • USP

  • (1043706)  Aspartame  United States Pharmacopeia (USP) Reference Standard

  • 22839-47-0

  • 1043706-200MG

  • 4,662.45CNY

  • Detail

22839-47-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name aspartame

1.2 Other means of identification

Product number -
Other names E 951

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:22839-47-0 SDS

22839-47-0Synthetic route

N-[N-[(phenylmethoxy)carbonyl]-L-α-aspartyl]-L-phenylalanine 4-(1,1-dimethylethyl) 1-methyl ester
27446-39-5

N-[N-[(phenylmethoxy)carbonyl]-L-α-aspartyl]-L-phenylalanine 4-(1,1-dimethylethyl) 1-methyl ester

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With hydrogen fluoride; methoxybenzene at 0℃; for 0.5h;98%
N-carbobenzyloxy-L-aspartyl-L-phenylalanine methyl ester
33605-72-0

N-carbobenzyloxy-L-aspartyl-L-phenylalanine methyl ester

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal97%
With hydrogen; palladium
(S)-N-((S)-1-Methoxycarbonyl-2-phenyl-ethyl)-3-(2-p-tolyl-acetylamino)-succinamic acid
140233-83-6

(S)-N-((S)-1-Methoxycarbonyl-2-phenyl-ethyl)-3-(2-p-tolyl-acetylamino)-succinamic acid

A

4-tolylacetic acid
622-47-9

4-tolylacetic acid

B

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With penicillin amidase at 25℃; for 3.8h; Rate constant; Product distribution;A n/a
B 90%
N-phenacetyl-α-L-aspartyl-L-phenylalanine methyl ester
101623-22-7

N-phenacetyl-α-L-aspartyl-L-phenylalanine methyl ester

A

phenylacetic acid
103-82-2

phenylacetic acid

B

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With pH 7.5; penicillinacylase on Eupergit C beads In water at 28℃;A n/a
B 87%
With penicillin amidase at 25℃; for 2.5h;A n/a
B 99 % Chromat.
With penicillin amidase at 25℃; for 2.5h; Rate constant; Product distribution;A n/a
B 99 % Chromat.
α-L-aspartyl-L-phenylalanine methyl ester hydrochloride
5910-52-1

α-L-aspartyl-L-phenylalanine methyl ester hydrochloride

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With sodium carbonate In water at 20℃; for 0.5h; pH=5;84%
With sodium carbonate In water pH=5.2;40%
methyl ester of N-tert-butyloxycarbonyl-L-aspartyl-L-phenylalanine
40944-73-8

methyl ester of N-tert-butyloxycarbonyl-L-aspartyl-L-phenylalanine

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane for 0.5h;83%
With TFA-anisole
N-formylaspartame
33605-76-4

N-formylaspartame

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With hydroxylamine hydrochloride In methanol83%
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

<(4S)-2,2-bis(trifluoromethyl)-5-oxo-1,3-oxazolidine-4-yl>acetate
131021-87-9

<(4S)-2,2-bis(trifluoromethyl)-5-oxo-1,3-oxazolidine-4-yl>acetate

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
In diethyl ether at 20℃; for 24h;72%
In diethyl ether; ethyl acetate Ambient temperature;
4N-hydrochloric acid

4N-hydrochloric acid

N-formylaspartame
33605-76-4

N-formylaspartame

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
In water; tert-butyl alcohol70%
(S)-3-Formylamino-N-(1-methoxycarbonyl-2-phenyl-ethyl)-succinamic acid

(S)-3-Formylamino-N-(1-methoxycarbonyl-2-phenyl-ethyl)-succinamic acid

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With hydrogenchloride In methanol for 0.5h; Heating;65%
anhydride du N-chloroacetyl-L-acide aspartique
41567-23-1

anhydride du N-chloroacetyl-L-acide aspartique

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

A

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

B

α-L-aspartyl-L-phenylalanine methyl ester hydrochloride
5910-52-1

α-L-aspartyl-L-phenylalanine methyl ester hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; acetic acid; thiourea; sodium chloride In methanol; 1,1-dichloroethane; waterA n/a
B 48%
(S)-N-((S)-1-Methoxycarbonyl-2-phenyl-ethyl)-3-[2-(4-nitro-phenyl)-acetylamino]-succinamic acid
140233-85-8

(S)-N-((S)-1-Methoxycarbonyl-2-phenyl-ethyl)-3-[2-(4-nitro-phenyl)-acetylamino]-succinamic acid

A

4-nitrobenzeneacetic acid
104-03-0

4-nitrobenzeneacetic acid

B

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With penicillin amidase at 25℃; for 8.3h; Rate constant; Product distribution;A n/a
B 30%
L-aspartic anhydride hydrochloride
104413-44-7

L-aspartic anhydride hydrochloride

methyl bisulfate
75-93-4

methyl bisulfate

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With sulfuric acid In methanol; 1,2-dichloro-ethane21.9%
L-aspartic anhydride hydrochloride
104413-44-7

L-aspartic anhydride hydrochloride

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
21.8%
n-formyl-l-aspartic anhydride
116147-62-7

n-formyl-l-aspartic anhydride

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With potassium hydroxide; hydroxylamine hydrochloride In methanol; ethyl acetate21%
L-aspartic anhydride hydrochloride
104413-44-7

L-aspartic anhydride hydrochloride

methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
In methanol; 1,2-dichloro-ethane19.2%
Boc-Asp(OtBu)-Phe-OMe
4976-94-7

Boc-Asp(OtBu)-Phe-OMe

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With trifluoroacetic acid
Z-Asp(OBzl)-Phe-OMe
5262-07-7

Z-Asp(OBzl)-Phe-OMe

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With hydrogen; acetic acid; palladium
With hydrogenchloride; hydrogen; palladium on activated charcoal In methanol
With hydrogen; palladium on activated charcoal
With palladium on carbon; hydrogen In methanol for 4h;
methyl (2S)-2-amino-3-phenylpropanoate hydrochloride
7524-50-7

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

L-aspartic acid N-thiocarboxyanhydride
77217-04-0, 82522-65-4

L-aspartic acid N-thiocarboxyanhydride

A

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

B

aspartame
25548-16-7

aspartame

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide 1.) water, 0-5 deg C, pH 8.5-9.5, 2.) MeOH, water, 0 deg C, pH 4.5-5; Yield given. Multistep reaction. Yields of byproduct given;
(S)-2-[(2-Benzyl-5-oxo-isoxazolidine-3-carbonyl)-amino]-3-phenyl-propionic acid methyl ester
125507-05-3, 125507-06-4

(S)-2-[(2-Benzyl-5-oxo-isoxazolidine-3-carbonyl)-amino]-3-phenyl-propionic acid methyl ester

A

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

B

(R)-Asp-(S)-PhOMe
22839-66-3

(R)-Asp-(S)-PhOMe

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In ethanol; water at 20℃; under 760 Torr; for 5h; Yield given. Yields of byproduct given;
With hydrogen; palladium dihydroxide In ethanol; water at 20℃; under 1 Torr; for 5h; Yield given. Yields of byproduct given;
(S)-2-{[(S)-5-Oxo-2-((R)-1-phenyl-ethyl)-isoxazolidine-3-carbonyl]-amino}-3-phenyl-propionic acid methyl ester
125507-07-5, 125590-57-0, 125590-58-1

(S)-2-{[(S)-5-Oxo-2-((R)-1-phenyl-ethyl)-isoxazolidine-3-carbonyl]-amino}-3-phenyl-propionic acid methyl ester

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In ethanol; water at 70℃; under 760 Torr; for 5h;65 mg
(S)-N-((S)-1-Methoxycarbonyl-2-phenyl-ethyl)-3-[2-(4-methoxy-phenyl)-acetylamino]-succinamic acid
140233-84-7

(S)-N-((S)-1-Methoxycarbonyl-2-phenyl-ethyl)-3-[2-(4-methoxy-phenyl)-acetylamino]-succinamic acid

A

4-Methoxyphenylacetic acid
104-01-8

4-Methoxyphenylacetic acid

B

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With penicillin amidase at 25℃; for 7h; Product distribution; Rate constant;A n/a
B 92 % Chromat.
(S)-3-Benzyloxycarbonylamino-N-(1-methoxycarbonyl-2-phenyl-ethyl)-succinamic acid

(S)-3-Benzyloxycarbonylamino-N-(1-methoxycarbonyl-2-phenyl-ethyl)-succinamic acid

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal Yield given;
aspartame hemihydrate, form I, ball-milled

aspartame hemihydrate, form I, ball-milled

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
at 130℃; Kinetics;
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetonitrile / 2 h / Ambient temperature
2: H2 / Pd
View Scheme
Multi-step reaction with 2 steps
1: 1.) pyridine, triethylamine, pivaloyl chloride; 2.) DMFA, 1-hydroxybenzotriazole / 1.) THF, 20 min, -10 deg C; 2.) CHCl3, 1.5 h 20 deg C
2: 83 percent / 4 N HCl / dioxane / 0.5 h
View Scheme
Multi-step reaction with 3 steps
1: 1.) pyridine, triethylamine, pivaloyl chloride; 2.) DMFA, 1-hydroxybenzotriazole / 1.) THF; 2.) CHCl3
2: hydrogen / Pd/C / acetic acid
3: 83 percent / 4 N HCl / dioxane / 0.5 h
View Scheme
L,L-N-t-Boc-Asp(OBz)-PM
104413-52-7

L,L-N-t-Boc-Asp(OBz)-PM

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogen / Pd/C / acetic acid
2: 83 percent / 4 N HCl / dioxane / 0.5 h
View Scheme
Multi-step reaction with 2 steps
1: 66 percent / H2 / Pd / methanol; acetic acid / 3 h
2: TFA-anisole
View Scheme
L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Asp-Phe-NH2
5241-71-4

Asp-Phe-NH2

Conditions
ConditionsYield
With ammonia at -40℃; for 10.25h;97%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

A

N-[(1,1-dimethylethoxy)carbonyl]-(L)-α-aspartyl-(L)-phenylalanine methyl ester mono(sodium) salt
222641-22-7

N-[(1,1-dimethylethoxy)carbonyl]-(L)-α-aspartyl-(L)-phenylalanine methyl ester mono(sodium) salt

B

N-[(1,1-dimethylethoxy)carbonyl]-(L)-α-aspartyl-(L)-phenylalanine mono(sodium) salt

N-[(1,1-dimethylethoxy)carbonyl]-(L)-α-aspartyl-(L)-phenylalanine mono(sodium) salt

Conditions
ConditionsYield
With sodium hydroxide In methanol; water; ethyl acetateA n/a
B 97%
dichloro(p-cymene)ruthenium(II) dimer

dichloro(p-cymene)ruthenium(II) dimer

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

sodium methylate
124-41-4

sodium methylate

{(η6-p-cymene)Ru(L-aspartyl-L-phenylalaninemethylester)}Cl

{(η6-p-cymene)Ru(L-aspartyl-L-phenylalaninemethylester)}Cl

Conditions
ConditionsYield
In methanol byproducts: NaCl; under Ar, addn. of 2 equivalents NaOMe-soln. to Ru-compd. and 2 equivalents of ligand in methanol, stirred for 30 min at room temp.; evapd. in vac., residue taken up in CH2Cl2, centrifuge (NaCl), dropwise addn. to pentane; elem. anal.;97%
L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

((L)-α-aspartyl)-(L)-phenylalaninamide ammonium salt

((L)-α-aspartyl)-(L)-phenylalaninamide ammonium salt

Conditions
ConditionsYield
With ammonia at -40℃; for 1.5h;95%
L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

[(2S,5S)-5-benzyl-3,6-dioxopiperazin-2-yl]acetic acid
5262-10-2

[(2S,5S)-5-benzyl-3,6-dioxopiperazin-2-yl]acetic acid

Conditions
ConditionsYield
at 200℃; for 0.333333h;92%
In dimethyl sulfoxide at 80℃; for 8h;88%
at 180℃; Kinetics;
methanol
67-56-1

methanol

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

N-α-L-aspartyl-L-phenylalanine dimethyl ester hydrochloride

N-α-L-aspartyl-L-phenylalanine dimethyl ester hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 0 - 25℃; Schlenk technique; Inert atmosphere;91%
nicotinoyl azide
4013-72-3

nicotinoyl azide

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

Nα-nicotinoyl-L-aspartyl-L-phenylalanine methyl ester

Nα-nicotinoyl-L-aspartyl-L-phenylalanine methyl ester

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0℃; for 3h;90%
(2R, 4R)-monatin sodium salt

(2R, 4R)-monatin sodium salt

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

mixed crystals (salt) of (2R,4R)-monatin and aspartame

mixed crystals (salt) of (2R,4R)-monatin and aspartame

Conditions
ConditionsYield
With hydrogenchloride In water at 50℃; for 0.166667h;87.2%
dichloro(p-cymene)ruthenium(II) dimer

dichloro(p-cymene)ruthenium(II) dimer

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

sodium methylate
124-41-4

sodium methylate

(η6-p-cymene)Ru(L-aspartyl-L-phenylalaninemethylester(2-))*H2O

(η6-p-cymene)Ru(L-aspartyl-L-phenylalaninemethylester(2-))*H2O

Conditions
ConditionsYield
In methanol byproducts: NaCl; under Ar, addn. of 4 equivalents NaOMe-soln. to Ru-compd. and 2 equivalents of ligand in methanol, stirred for 1.5 h min at room temp.; evapd. in vac., residue taken up in CH2Cl2, centrifuge (NaCl), dropwise addn. to pentane, diffusion of ether into a methanolic soln.; elem. anal.;86%
3,3-dimethylbutyrylaldehyde
2987-16-8

3,3-dimethylbutyrylaldehyde

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

neotame
165450-17-9

neotame

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon In methanol; water at 20℃; for 6h;85%
With hydrogen; palladium on activated charcoal under 1551.44 Torr; for 12h; Condensation; reduction; room t.;56%
With hydrogen; palladium on activated charcoal In methanol at 20℃; under 1551.44 Torr; for 12h; Hydrogenation; reductive alkylation;56%
3-(3-benzyloxy-4-methoxyphenyl)acrylaldehyde
76678-64-3

3-(3-benzyloxy-4-methoxyphenyl)acrylaldehyde

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

N-[N-[3-(3-hydroxy-4-methoxyphenyl)propenyl]-L-aspartyl]-L-phenylalanine-1-methyl ester

N-[N-[3-(3-hydroxy-4-methoxyphenyl)propenyl]-L-aspartyl]-L-phenylalanine-1-methyl ester

Conditions
ConditionsYield
With sodium tetrahydroborate; acetic acid at 10 - 20℃; for 2h;85%
L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

L-phenylalanine
63-91-2

L-phenylalanine

Conditions
ConditionsYield
With sodium hydroxide for 6h; Heating;83%
L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

(1,1,1-trifluoroethyl) phenyl iodonium (N,N'-bis-trifluoromethylsulfonyl) imide
307501-98-0

(1,1,1-trifluoroethyl) phenyl iodonium (N,N'-bis-trifluoromethylsulfonyl) imide

L-Asp-L-Phe-OMe

L-Asp-L-Phe-OMe

Conditions
ConditionsYield
80%
L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

sodium 3-benzyl-6-(carboxylatomethyl)-2,5-dioxopiperazine
136983-81-8

sodium 3-benzyl-6-(carboxylatomethyl)-2,5-dioxopiperazine

Conditions
ConditionsYield
With sodium hydroxide In water78%
3-(3-benzyloxy-4-methoxyphenyl)acrylaldehyde
76678-64-3

3-(3-benzyloxy-4-methoxyphenyl)acrylaldehyde

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

N-[N-[3-(3-benzyloxy-4-methoxyphenyl)propenyl]-L-aspartyl]-L-phenylalanine-1-methyl ester

N-[N-[3-(3-benzyloxy-4-methoxyphenyl)propenyl]-L-aspartyl]-L-phenylalanine-1-methyl ester

Conditions
ConditionsYield
With sodium tetrahydroborate; acetic acid at 10℃;78%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

methyl ester of N-tert-butyloxycarbonyl-L-aspartyl-L-phenylalanine
40944-73-8

methyl ester of N-tert-butyloxycarbonyl-L-aspartyl-L-phenylalanine

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; water at 20℃; for 18h;72%
L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

2-azido-α-L-aspartyl-L-phenylalanine methyl ester

2-azido-α-L-aspartyl-L-phenylalanine methyl ester

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; triflic azide; potassium carbonate; sodium hydroxide In methanol; dichloromethane; water at 20℃; for 18h; pH=9 - 9.5;70%
L-Asp-L-Phe-OMe
22839-47-0

L-Asp-L-Phe-OMe

(3-hydroxy-4-methoxy)cinnamaldehyde

(3-hydroxy-4-methoxy)cinnamaldehyde

N-[N-[3-(3-hydroxy-4-methoxyphenyl)propyl]-L-aspartyl]-L-phenylalanine-1-methyl ester

N-[N-[3-(3-hydroxy-4-methoxyphenyl)propyl]-L-aspartyl]-L-phenylalanine-1-methyl ester

Conditions
ConditionsYield
Stage #1: L-Asp-L-Phe-OMe; 3-hydroxy-4-methoxycinnamalaldehyde With sodium tetrahydroborate; acetic acid at 10 - 20℃; for 2h;
Stage #2: With 5%-palladium/activated carbon; hydrogen In ethanol; water under 2585.81 Torr; for 10h;
66%

22839-47-0Relevant articles and documents

Lelj et al.

, p. 6669,6670 (1976)

Investigation of solid-state reactions using variable temperature X-ray powder diffractrometry. I. Aspartame hemihydrate

Rastogi,Zakrzewski,Suryanarayanan

, p. 267 - 273 (2001)

Purpose. The object of this study was to demonstrate the applicability of variable temperature X-ray powder diffractometry (XRD) to investigate solid-state reactions using aspartame as a model compound. Methods. Aspartame exists as a hemihydrate (ASH) under ambient conditions and converts to aspartame anhydrate (ASA) at ~130°C. ASA on further heating to ~180°C undergoes decomposition (intramolecular cyclization) to form a diketopiperazine derivative (DKP). The dehydration as well as the decomposition kinetics were studied isothermally at several temperatures. The unique feature of this technique is that it permits simultaneous quantification of the reactant as well as the product. Results. While the dehydration of ASH appeared to follow first-order kinetics, the cyclization of ASA was a nucleation controlled process. The rate constants were obtained at various temperatures, which permitted the calculation of the activation energies of dehydration and cyclization from the Arrhenius plots. The activation energy of dehydration was also calculated according to the method described by Ng (Aust. J. Chem., 28:1169-1178, 1975) and the two values were in good agreement. Conclusions. The study demonstrates that XRD is an excellent complement to thermal analysis and provides direct information about the solid-states of various reaction phases.

STUDIES ON AMINO ACIDS AND PEPTIDES - VII SYNTHESES OF ASPARTAME AND THIOASPARTAME

Yde, B.,Thomsen, I.,Thorsen, M.,Clausen,K.,Lawesson, S.-O.

, p. 4121 - 4126 (1983)

The protected aspartame, 4, has been prepared from the benzyl ester of N-benzyloxycarbonyl-S-aspartic acid, 1, and the methyl S-phenylalanate, 3, using 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide, LR, as a coupling reagent.Another protected aspartame, 7, has been prepared from the tert-butyl ester of 1--succinimide, 6, and methyl S-phenylalanate, 3.Thiations of 4/7 by LR produces a protected thioaspartame, 5/9.Deprotection of 7 and 9 gives aspartame, 8, and the slightly sweet thioaspartame, 10, in high yields.

METHOD FOR THE SYNTHESIS OF PEPTIDES WITHOUT SOLVENT

-

Page/Page column 6, (2010/02/17)

The disclosure relates to a method for the synthesis of a compound of the formula (I) in which: n is an integer higher than or equal to 1; Rb and each Rn are independently a hydrogen atom, a C1-C6 arylalkyl group or a C1-C6 alkyl group substituted or not by an aryl group, —COOH, C1-C6, —COO-(alkyl), —CONH2, —SH, heteroaryl, —NH2, —NHC(NH)(NH2), C1-C6-s-(alkyl), —OH or phenol; Ra is a N-protective group; Rc is a ORd group in which Rd is a C1-C6 alkyl group or a NReRf group in which Re and Rf Re independently an N-protective group.

Hexafluoroacetone as protection and activation reagent in amino acid and peptide chemistry regiospecific α-functionalization of aspartic acid

Burger, Klaus,Lange, Torsten,Rudolph, Martin

, p. 189 - 198 (2007/10/03)

A highly efficient method for regiospecific α-functionalization of aspartic acid is described. Key step is the synthesis of a N-protected and regioselectively α-carboxy-activated heterocyclic intermediate from aspartic acid and hexafluoroacetone. The new strategy offers i.a. a two step access to the sweetener Aspartame and to libraries of aspartame analogues.

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