Aspartyl phenylalanine methyl ester (CAS 22839-47-0) — formula C14H18N2O5, molecular weight 294.30; category chemical.
| CAS Number | 22839-47-0 |
|---|---|
| Molecular Formula | C14H18N2O5 |
| Molecular Weight | 294.30 |
| Melting Point | 246.5 °C |
| LogP | -0.1 |
| Applications | Uses: Used as a non-nutritive sweetener, [Merck Index] Used as a flavor enhancer and non-nutritive sweetener, [FDA], A synthetic, non-nutritive sweetener approved by FDA for tabletop use and as a packaged food additive. The U.S., Canada and South Africa permit its use in carbonated beverages. A combination of aspartic acid and L-phenylalanine is said to be about 200 times sweeter than sugar., Nutrasweet (TM), ... Used as a table sweetener for coffee, tea, breakfast cereals, etc ... Other food applications identified include pre-sweetened breakfast cereals, chewing gum, and dry bases for beverages such as instant coffee and tea, gelatins, puddings and fillings, and dairy-product analogue whipped toppings., Use Classification: Food additives, Food Additives -> SWEETENER -> JECFA Functional Classes, Cosmetics -> Masking, Industry Uses: Other, Household Products: Cosmetics product ingredient: Aspartame, Product count: 1, Information on 1 consumer products that contain Aspartame in the following categories is provided:, • Personal Care, Methods of Manufacturing: Aspartame is produced by coupling together L-phenylalanine (or L-phenylalanine methyl ester) and L-aspartic acid, either chemically or enzymatically. The former procedure yields both the sweet alpha-aspartame and nonsweet beta-aspartame from which the alpha aspartame has to be separated and purified. The enzymatic process yields only alpha-aspartame., Production of aspartame normally starts from L-aspartic acid and L-phenylalanine or L-phenylalanine methyl ester. The production follows common routes of peptide synthesis, as the L-configuration of amino acids has to be retained (essential for sweetness). Common production routes require protective groups for aspartic acid. The protective groups commonly used in peptide synthesis have been suggested for aspartame synthesis, but simple protection for large-scale production can be obtained by use of formylaspartic acid anhydride. It can be reacted with phenylalanine methyl ester to N-formylaspartame, from which the protective group has to be removed. Especially simple production is possible from N-formylaspartic acid anhydride and L-phenylalanine. The resulting N-formylaspartylphenylalanine is treated with hydrochloric acid and methanol. The aspartame hydrochloride obtained can be crystallized for purification and transformed into aspartame after addition of a stoichiometric amount of a neutralizing agent. Adjustment of the solvent increases the yield by improving the ratio of alpha- to beta-isomers. Crystallization of alpha-aspartame hydrohalides is a suitable purification step, as beta-hydrohalides are more soluble., Method for large-scale production of aspartame ... L-aspartic acid anhydride is condensed with L-phenylalanine methyl ester to form a mixture of beta-L-aspartyl-L-phenylalanine methyl ester and alpha-L-aspartyl-L-phenylalanine methyl ester. On acidification with hydrochloric acid, the latter precipitates and the precipitate is neutralized to form aspartame., From table, Impurities: Diketopiperazine, Formulations, Preparations: As a table-top sweetener ..., aspartame, is spray-dried with partially hydrolyzed corn starch., Canderel, Formulation name, Equal, NatraTaste, For more Formulations, Preparations (Complete) data for Aspartame (9 total), please visit the HSDB record page., Consumption Patterns: (1992) 8, 040 tons in US, U.S. Production: 2023: <50, 000 lb, 2022: 50, 000 - <250, 2021: 50, 2020: <50, General Manufacturing Information: Food, beverage, and tobacco product manufacturing, L-Phenylalanine, L-.alpha.-aspartyl-, 2-methyl ester: ACTIVE, Aspartame is the methylester of a dipeptide composed of two amino acids, phenylalanine and aspartic acid. When these two amino acids are so combined to form aspartame (1-methyl N -L-a-aspartyl-L-phenylalanine), they produce an intensely sweet-tasting substance, approximately 180 times as sweet as sucrose., A combination of aspartame with either granular or fused mannitol in a 1:9 ratio can provide a suitable base for chewable tablets with respect to sweetness, mouth feel, absence of unpleasant aftertaste, and low caloric value. Both compounds are compatible with leucine., ... In the July 26, 1974, decision by the FDA to approve the use of aspartame, labeling provisions were made in which foods not containing protein or intended for admixture to protein sweetened with aspartame should bear the statement "contains protein." |
| Category | Sweeteners |
Documented applications: Uses: Used as a non-nutritive sweetener, [Merck Index] Used as a flavor enhancer and non-nutritive sweetener, [FDA], A synthetic, non-nutritive sweetener approved by FDA for tabletop use and as a packaged food additive. The U.S., Canada and South Africa permit its use in carbonated beverages. A combination of aspartic acid and L-phenylalanine is said to be about 200 times sweeter than sugar., Nutrasweet (TM), ... Used as a table sweetener for coffee, tea, breakfast cereals, etc ... Other food applications identified include pre-sweetened breakfast cereals, chewing gum, and dry bases for beverages such as instant coffee and tea, gelatins, puddings and fillings, and dairy-product analogue whipped toppings., Use Classification: Food additives, Food Additives -> SWEETENER -> JECFA Functional Classes, Cosmetics -> Masking, Industry Uses: Other, Household Products: Cosmetics product ingredient: Aspartame, Product count: 1, Information on 1 consumer products that contain Aspartame in the following categories is provided:, • Personal Care, Methods of Manufacturing: Aspartame is produced by coupling together L-phenylalanine (or L-phenylalanine methyl ester) and L-aspartic acid, either chemically or enzymatically. The former procedure yields both the sweet alpha-aspartame and nonsweet beta-aspartame from which the alpha aspartame has to be separated and purified. The enzymatic process yields only alpha-aspartame., Production of aspartame normally starts from L-aspartic acid and L-phenylalanine or L-phenylalanine methyl ester. The production follows common routes of peptide synthesis, as the L-configuration of amino acids has to be retained (essential for sweetness). Common production routes require protective groups for aspartic acid. The protective groups commonly used in peptide synthesis have been suggested for aspartame synthesis, but simple protection for large-scale production can be obtained by use of formylaspartic acid anhydride. It can be reacted with phenylalanine methyl ester to N-formylaspartame, from which the protective group has to be removed. Especially simple production is possible from N-formylaspartic acid anhydride and L-phenylalanine. The resulting N-formylaspartylphenylalanine is treated with hydrochloric acid and methanol. The aspartame hydrochloride obtained can be crystallized for purification and transformed into aspartame after addition of a stoichiometric amount of a neutralizing agent. Adjustment of the solvent increases the yield by improving the ratio of alpha- to beta-isomers. Crystallization of alpha-aspartame hydrohalides is a suitable purification step, as beta-hydrohalides are more soluble., Method for large-scale production of aspartame ... L-aspartic acid anhydride is condensed with L-phenylalanine methyl ester to form a mixture of beta-L-aspartyl-L-phenylalanine methyl ester and alpha-L-aspartyl-L-phenylalanine methyl ester. On acidification with hydrochloric acid, the latter precipitates and the precipitate is neutralized to form aspartame., From table, Impurities: Diketopiperazine, Formulations, Preparations: As a table-top sweetener ..., aspartame, is spray-dried with partially hydrolyzed corn starch., Canderel, Formulation name, Equal, NatraTaste, For more Formulations, Preparations (Complete) data for Aspartame (9 total), please visit the HSDB record page., Consumption Patterns: (1992) 8, 040 tons in US, U.S. Production: 2023: <50, 000 lb, 2022: 50, 000 - <250, 2021: 50, 2020: <50, General Manufacturing Information: Food, beverage, and tobacco product manufacturing, L-Phenylalanine, L-.alpha.-aspartyl-, 2-methyl ester: ACTIVE, Aspartame is the methylester of a dipeptide composed of two amino acids, phenylalanine and aspartic acid. When these two amino acids are so combined to form aspartame (1-methyl N -L-a-aspartyl-L-phenylalanine), they produce an intensely sweet-tasting substance, approximately 180 times as sweet as sucrose., A combination of aspartame with either granular or fused mannitol in a 1:9 ratio can provide a suitable base for chewable tablets with respect to sweetness, mouth feel, absence of unpleasant aftertaste, and low caloric value. Both compounds are compatible with leucine., ... In the July 26, 1974, decision by the FDA to approve the use of aspartame, labeling provisions were made in which foods not containing protein or intended for admixture to protein sweetened with aspartame should bear the statement "contains protein.".
Aspartyl phenylalanine methyl ester is a chemical compound with CAS registry number 22839-47-0 and molecular formula C14H18N2O5 (molecular weight 294.30), belonging to the chemical segment of chemical raw materials.
CAS number: 22839-47-0
Its molecular formula C14H18N2O5 comprises 14 C, 18 H, 2 N, 5 O atoms.
Also known as: Aspartyl phenylalanine methyl ester · Aspartame · APM
Category: chemical
The CAS registry number of Aspartyl phenylalanine methyl ester is 22839-47-0.
Molecular formula C14H18N2O5, molecular weight 294.30.
It is also registered under: Aspartyl phenylalanine methyl ester, Aspartame, APM.
Recorded applications: Uses: Used as a non-nutritive sweetener, [Merck Index] Used as a flavor enhancer and non-nutritive sweetener, [FDA], A synthetic, non-nutritive sweetener approved by FDA for tabletop use and as a packaged food additive. The U.S., Canada and South Africa permit its use in carbonated beverages. A combination of aspartic acid and L-phenylalanine is said to be about 200 times sweeter than sugar., Nutrasweet (TM), ... Used as a table sweetener for coffee, tea, breakfast cereals, etc ... Other food applications identified include pre-sweetened breakfast cereals, chewing gum, and dry bases for beverages such as instant coffee and tea, gelatins, puddings and fillings, and dairy-product analogue whipped toppings., Use Classification: Food additives, Food Additives -> SWEETENER -> JECFA Functional Classes, Cosmetics -> Masking, Industry Uses: Other, Household Products: Cosmetics product ingredient: Aspartame, Product count: 1, Information on 1 consumer products that contain Aspartame in the following categories is provided:, • Personal Care, Methods of Manufacturing: Aspartame is produced by coupling together L-phenylalanine (or L-phenylalanine methyl ester) and L-aspartic acid, either chemically or enzymatically. The former procedure yields both the sweet alpha-aspartame and nonsweet beta-aspartame from which the alpha aspartame has to be separated and purified. The enzymatic process yields only alpha-aspartame., Production of aspartame normally starts from L-aspartic acid and L-phenylalanine or L-phenylalanine methyl ester. The production follows common routes of peptide synthesis, as the L-configuration of amino acids has to be retained (essential for sweetness). Common production routes require protective groups for aspartic acid. The protective groups commonly used in peptide synthesis have been suggested for aspartame synthesis, but simple protection for large-scale production can be obtained by use of formylaspartic acid anhydride. It can be reacted with phenylalanine methyl ester to N-formylaspartame, from which the protective group has to be removed. Especially simple production is possible from N-formylaspartic acid anhydride and L-phenylalanine. The resulting N-formylaspartylphenylalanine is treated with hydrochloric acid and methanol. The aspartame hydrochloride obtained can be crystallized for purification and transformed into aspartame after addition of a stoichiometric amount of a neutralizing agent. Adjustment of the solvent increases the yield by improving the ratio of alpha- to beta-isomers. Crystallization of alpha-aspartame hydrohalides is a suitable purification step, as beta-hydrohalides are more soluble., Method for large-scale production of aspartame ... L-aspartic acid anhydride is condensed with L-phenylalanine methyl ester to form a mixture of beta-L-aspartyl-L-phenylalanine methyl ester and alpha-L-aspartyl-L-phenylalanine methyl ester. On acidification with hydrochloric acid, the latter precipitates and the precipitate is neutralized to form aspartame., From table, Impurities: Diketopiperazine, Formulations, Preparations: As a table-top sweetener ..., aspartame, is spray-dried with partially hydrolyzed corn starch., Canderel, Formulation name, Equal, NatraTaste, For more Formulations, Preparations (Complete) data for Aspartame (9 total), please visit the HSDB record page., Consumption Patterns: (1992) 8, 040 tons in US, U.S. Production: 2023: <50, 000 lb, 2022: 50, 000 - <250, 2021: 50, 2020: <50, General Manufacturing Information: Food, beverage, and tobacco product manufacturing, L-Phenylalanine, L-.alpha.-aspartyl-, 2-methyl ester: ACTIVE, Aspartame is the methylester of a dipeptide composed of two amino acids, phenylalanine and aspartic acid. When these two amino acids are so combined to form aspartame (1-methyl N -L-a-aspartyl-L-phenylalanine), they produce an intensely sweet-tasting substance, approximately 180 times as sweet as sucrose., A combination of aspartame with either granular or fused mannitol in a 1:9 ratio can provide a suitable base for chewable tablets with respect to sweetness, mouth feel, absence of unpleasant aftertaste, and low caloric value. Both compounds are compatible with leucine., ... In the July 26, 1974, decision by the FDA to approve the use of aspartame, labeling provisions were made in which foods not containing protein or intended for admixture to protein sweetened with aspartame should bear the statement "contains protein.".
Category: Sweeteners.
Independent reference data for Aspartyl phenylalanine methyl ester (CAS 22839-47-0), compiled from public chemistry databases.
| CAS 号 | 22839-47-0 |
|---|---|
| PubChem CID | 134601 |
| 分子式 | C14H18N2O5 |
| 分子量 | 294.12 g/mol |
| IUPAC 名称 | (3S)-3-amino-4-[[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid |
| InChIKey | IAOZJIPTCAWIRG-QWRGUYRKSA-N |
| UNII（FDA） | Z0H242BBR1 |
| ChEBI 编号 | CHEBI:195544 |
| Molecular Weight | 294.30 |
|---|---|
| XLogP3 | -2.7 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 8 |
| Exact Mass | 294.12157168 |
| Monoisotopic Mass | 294.12157168 |
| Topological Polar Surface Area | 119 |
| Heavy Atom Count | 21 |
| Melting Point | 246.5 °C |
|---|---|
| LogP | -0.1 |
| Dissociation Constants | 3.19 |
| Dissociation Constants | 7.87 |
| Collision Cross Section | 127.4 Ų [M+H]+ |
| Collision Cross Section | 126.6 Ų [M-H]- |
aspartame; 22839-47-0; Nutrasweet; Asp-phe-ome; Aspartam; Aspartamo; Sweet dipeptide; L-Aspartyl-L-phenylalanine methyl ester; Aspartamum; Dipeptide sweetener; Equal; Methyl aspartylphenylalanate; Aspartylphenylalanine methyl ester; Pal Sweet; Sladex; Zero-cal
| 法规与食品接触 | FDA Substance added to food: FLAVOR ENHANCER, NON-NUTRITIVE SWEETENER SWEETENER: Food Additives 0â40 mg/kg bw TRS 1050-JECFA 96/3 FAS 87-JECFA 96/1 |
|---|---|
| GHS 通报统计 | 96.9% (186 / 192) |
| GHS 通报统计 | 96.9% (186 / 192) |
|---|
Aspartame 的 CAS 号为 22839-47-0，分子式 C14H18N2O5，分子量 294.12 g/mol。 UNII Z0H242BBR1; ChEBI 195544; InChIKey IAOZJIPTCAWIRG-QWRGUYRKSA-N. Melting Point: 246.5 °C; LogP: -0.1; Dissociation Constants: 3.19.
Source: PubChem / Wikidata; the batch COA governs where values differ.
Supplier: Jinan Shenghe Chemical Co., Ltd.