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Chemistry

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Also known as: 22839-47-0, Nutrasweet, Asp-phe-ome, Asp-phe methyl ester, Aspartam, Canderel
Molecular Formula
C14H18N2O5
Molecular Weight
294.30  g/mol
InChI Key
IAOZJIPTCAWIRG-QWRGUYRKSA-N
FDA UNII
Z0H242BBR1

Aspartame
Flavoring agent sweeter than sugar, metabolized as PHENYLALANINE and ASPARTIC ACID.
1 2D Structure

Aspartame

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(3S)-3-amino-4-[[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid
2.1.2 InChI
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
2.1.3 InChI Key
IAOZJIPTCAWIRG-QWRGUYRKSA-N
2.1.4 Canonical SMILES
COC(=O)C(CC1=CC=CC=C1)NC(=O)C(CC(=O)O)N
2.1.5 Isomeric SMILES
COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(=O)O)N
2.2 Other Identifiers
2.2.1 UNII
Z0H242BBR1
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Aspartylphenylalanine Methyl Ester

2. Aspartylphenylalanine, Methyl

3. Canderel

4. Gold, Hermesetas

5. Goldswite

6. Hermesetas Gold

7. Methyl Aspartylphenylalanine

8. Methyl Ester, Aspartylphenylalanine

9. Milisucre

10. Nozucar

11. Nutrasweet

12. Sc 18862

13. Sc-18862

14. Sc18862

15. Tri Sweet

16. Tri-sweet

17. Trisweet

2.3.2 Depositor-Supplied Synonyms

1. 22839-47-0

2. Nutrasweet

3. Asp-phe-ome

4. Asp-phe Methyl Ester

5. Aspartam

6. Canderel

7. L-aspartyl-l-phenylalanine Methyl Ester

8. Aspartamo

9. Aspartamum

10. Aspartylphenylalanine Methyl Ester

11. Equal

12. Sweet Dipeptide

13. Methyl Aspartylphenylalanate

14. Dipeptide Sweetener

15. Pal Sweet

16. H-asp-phe-ome

17. 1-methyl N-l-alpha-aspartyl-l-phenylalanate

18. Tri-sweet

19. Sladex

20. Zero-cal

21. Methyl L-alpha-aspartyl-l-phenylalaninate

22. Sc-18862

23. 3-amino-n-(alpha-methoxycarbonylphenethyl) Succinamic Acid

24. (s)-3-amino-4-(((s)-1-methoxy-1-oxo-3-phenylpropan-2-yl)amino)-4-oxobutanoic Acid

25. Chebi:2877

26. N-l-alpha-aspartyl-l-phenylalanine 1-methyl Ester

27. 3-amino-n-(alpha-carboxyphenethyl)succinamic Acid N-methyl Ester

28. Aspartame (e951)

29. Ins No.951

30. (3s)-3-amino-4-[[(2s)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic Acid

31. N-l-alpha-aspartyl-l-phenylalanine Methyl Ester

32. Nsc-758953

33. Ins-951

34. Z0h242bbr1

35. (s)-3-amino-4-((s)-1-methoxy-1-oxo-3-phenylpropan-2-ylamino)-4-oxobutanoic Acid

36. L-aspartyl-l-phenylalanyl Methyl Ester

37. Aspartame 1000 Microg/ml In Methanol

38. N-l-alpha-aspartyl L-phenylalanine 1-methyl Ester

39. Ncgc00091104-02

40. Dsstox_cid_107

41. E 951

42. E-951

43. Mfcd00002724

44. Dsstox_rid_75371

45. Dsstox_gsid_20107

46. Sanecta

47. Aspartam [inn-french]

48. Aspartame, L,l-alpha-

49. Aspartamum [inn-latin]

50. Aspartamo [inn-spanish]

51. Smr000471870

52. Cas-22839-47-0

53. Ccris 5456

54. Sc 18862

55. Hsdb 3915

56. Methyl L-aspartyl-l-phenylalanine

57. Einecs 245-261-3

58. L-phenylalanine, N-l-.alpha.-aspartyl-, 1-methyl Ester

59. Methyl L-alpha-aspartyl-l-phenylalanate

60. Unii-z0h242bbr1

61. Aminosweet

62. L-phenylalanine, N-l-alpha-aspartyl-, 1-methyl Ester

63. Palsweet Diet

64. Methyl N-l-alpha-aspartyl-l-phenylalaninate

65. 1-methyl N-l-alpha-aspartyl-l-phenylalanine

66. Aspartame [usan:inn:ban:nf]

67. L-alpha-aspartyl-l-phenylalanine 2-methyl Ester

68. Ncgc00095160-01

69. Df-ome

70. Aspartame (nf/inn)

71. N-(l-a-aspartyl)-l-phenylalanine Methyl Ester

72. Aspartame [fcc]

73. Aspartame [inn]

74. Aspartame [ii]

75. Aspartame [mi]

76. Aspartame [fhfi]

77. Aspartame [hsdb]

78. Aspartame [inci]

79. Aspartame [usan]

80. Spectrum2_001706

81. Spectrum3_001949

82. Aspartame [vandf]

83. Aspartame [mart.]

84. Epitope Id:164026

85. 3-amino-n-(alpha-carboxyphenethyl)succinamic Acid N-methyl Ester, Stereoisomer

86. Aspartame [usp-rs]

87. Aspartame [who-dd]

88. Schembl3636

89. Succinamic Acid, 3-amino-n-(alpha-carboxyphenethyl)-, N-methyl Ester, Stereoisomer

90. Bspbio_003549

91. Mls001066421

92. Mls001306461

93. Aspartame, Analytical Standard

94. Spectrum1505306

95. L-phenylalanine, L-alpha-aspartyl-, 2-methyl Ester

96. Spbio_001692

97. 3-amino-n-(.alpha.-carboxyphenethyl)succinamic Acid N-methyl Ester

98. Chembl171679

99. Aspartame [ep Monograph]

100. Dtxsid0020107

101. Asp-phe Methyl Ester, >=98%

102. Kbio3_002839

103. Aspartyl-phenylalanine Methyl Ester

104. Hms1922b16

105. Hms2093b05

106. Hms2233d15

107. Pharmakon1600-01505306

108. Hy-b0361

109. Zinc1532132

110. Tox21_111080

111. Tox21_111459

112. Tox21_202315

113. Tox21_302965

114. Aspartame 1000 Microg/ml In Water

115. Ccg-39444

116. Nsc758953

117. S2036

118. Akos015920055

119. Tert-butyln-(3-formylphenyl)carbamate

120. Tox21_111080_1

121. Am84801

122. Db00168

123. Nsc 758953

124. Alpha-aspartyl-phenylalanine Methyl Ester

125. L-aspartyl-l-phenyl-alanine Methyl Ester

126. Ncgc00091104-01

127. Ncgc00091104-03

128. Ncgc00091104-04

129. Ncgc00091104-05

130. Ncgc00095160-03

131. Ncgc00256407-01

132. Ncgc00259864-01

133. 7421-84-3

134. Ac-12293

135. As-13889

136. E951

137. L-aspartyl-l-3-phenylalanine Methyl Ester

138. Sbi-0206757.p001

139. Asp-phe Methyl Ester, >=99.0% (hplc)

140. A0997

141. Am20060556

142. Sw219179-1

143. Alpha-l-aspartyl-l-phenylalanine Methyl Ester

144. L-aspartyl-l-phenylalanine Methyl Ester, 96%

145. 39a470

146. D02381

147. Ab00376622_08

148. Ab00376622_09

149. A816383

150. Q182040

151. Sr-05000001682

152. J-502447

153. Sr-05000001682-1

154. Brd-k78841970-001-06-2

155. Aspartame, European Pharmacopoeia (ep) Reference Standard

156. Aspartame, United States Pharmacopeia (usp) Reference Standard

157. (s)-3-amino-n-((s)-1-methoxycarbonyl-2-phenyl-ethyl)-succinamic Acid

158. Aspartame, Pharmaceutical Secondary Standard; Certified Reference Material

159. (3s)-3-amino-3-{[(2s)-1-methoxy-1-oxo-3-phenylpropan-2-yl]carbamoyl}propanoic Acid

160. (s)-3-amino-4-(((s)-1-methoxy-1-oxo-3-phenylpropan-2-yl)amino)-4-oxobutanoicacid

161. 3-amino-4-[(1-carboxy-2-phenyl-ethyl)-methyl-amino]-4-oxo-butanoic Acid;n-l-alpha-aspartyl-l-phenylalanine Methyl Ester

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 294.30 g/mol
Molecular Formula C14H18N2O5
XLogP3-2.7
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count8
Exact Mass294.12157168 g/mol
Monoisotopic Mass294.12157168 g/mol
Topological Polar Surface Area119 Ų
Heavy Atom Count21
Formal Charge0
Complexity380
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Aspartame is used as an intense sweetening agent ... 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 80-200 times that of sucrose.

Rowe, R.C., Sheskey, P.J., Quinn, M.E.; (Eds.), Handbook of Pharmaceutical Excipients 6th edition Pharmaceutical Press, London, England 2009, p. 48


4.2 Drug Warning

Aspartame is the methylester of a dipeptide composed of two amino acids, phenylalanine and aspartic acid. ... Persons with phenylketonuria, who must restrict carefully their phenylalanine intake, must be alerted to the presence of phenylalanine in the drug product and the amount of the ingredient in each dosage unit.

21 CFR 201.21 (USFDA); Declaration of presence of phenylalanine as a component of aspartame in over-the-counter and prescrpition drugs for human use


Excessive use of aspartame should be avoided by patients with phenylketonuria.

Reynolds, J.E.F., Prasad, A.B. (eds.) Martindale-The Extra Pharmacopoeia. 28th ed. London: The Pharmaceutical Press, 1982., p. 425


Aspartic acid and sodium glutamate were both neuroexcitatory amino acids which had an additive toxic effect on hypothalamic neurones. As this might be specially damaging to young children, who already receive sodium glutamate in gram quantities in their diet, aspartame should not generally be added to children's food.

Reynolds, J.E.F., Prasad, A.B. (eds.) Martindale-The Extra Pharmacopoeia. 28th ed. London: The Pharmaceutical Press, 1982., p. 425


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 ...

Rowe, R.C., Sheskey, P.J., Quinn, M.E.; (Eds.), Handbook of Pharmaceutical Excipients 6th edition Pharmaceutical Press, London, England 2009, p. 49


For more Drug Warnings (Complete) data for Aspartame (8 total), please visit the HSDB record page.


4.3 Drug Indication

Used as a diet supplement and sugar substitute.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Aspartame (L-alpha-aspartyl-L-phenylalanine methyl ester) is a low-calorie sweetener used to sweeten a wide variety of low- and reduced-calorie foods and beverages, including low-calorie tabletop sweeteners. Aspartame is composed of two amino acids, aspartic acid and phenylalanine, as the methyl ester. Aspartic acid and phenylalanine are also found naturally in protein containing foods, including meats, grains and dairy products. Methyl esters are also found naturally in many foods such as fruits and vegetable and their juices. Upon digestion, aspartame breaks down into three components (aspartic acid, phenylalanine and methanol), which are then absorbed into the blood and used in normal body processes. Neither aspartame nor its components accumulates in the body. These components are used in the body in the same ways as when they are derived from common foods.


5.2 MeSH Pharmacological Classification

Sweetening Agents

Substances that sweeten food, beverages, medications, etc., such as sugar, saccharine or other low-calorie synthetic products. (From Random House Unabridged Dictionary, 2d ed) (See all compounds classified as Sweetening Agents.)


5.3 Absorption, Distribution and Excretion

Absorption

Absorbed in the small intestine, aspartame is metabolized and absorbed very quickly.


5.4 Metabolism/Metabolites

Approximately 10% of aspartame (by weight) is broken down into methanol in the small intestine. Most of the methanol is absorbed and quickly converted into formaldehyde. Approximately 50% of aspartame (by weight) is broken down into phenylalanine. Approximately 40% of aspartame (by mass) is broken down into aspartic acid.


Unlike some other intense sweeteners, aspartame is metabolized in the body and consequently has some nutritive value: 1 g provides approx 17 kJ (4 kcal). However, in practice, the small quantity of aspartame consumed provides a minimal nutritive effect.

Rowe, R.C., Sheskey, P.J., Quinn, M.E.; (Eds.), Handbook of Pharmaceutical Excipients 6th edition Pharmaceutical Press, London, England 2009, p. 48


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.

Rowe, R.C., Sheskey, P.J., Quinn, M.E.; (Eds.), Handbook of Pharmaceutical Excipients 6th edition Pharmaceutical Press, London, England 2009, p. 49


Aspartame [SC-18862; 3-amino-N-(alpha-carboxyphenethyl) succinamic acid, methyl ester, the methyl ester of aspartylphenylalanine] is a sweetening agent that organoleptically has about 180 times the sweetness of sugar. The metabolism of aspartame has been studied in mice, rats, rabbits, dogs, monkeys, and humans. The compound was digested in all species in the same way as are natural constituents of the diet. Hydrolysis of the methyl group by intestinal esterases yielded methanol, which was oxidized in the one-carbon metabolic pool to CO2. The resultant dipeptide was split at the mucosal surface by dipeptidases and the free amino acids were absorbed. The aspartic acid moiety was transformed in large part to CO2 through its entry into the tricarboxylic acid cycle. Phenylalanine was primarily incorporated into body protein either unchanged or as its major metabolite, tyrosine.

PMID:827618 Ranney RE, et al; J Toxicol Environ Health 2 (2): 441-51 (1976).


Although aspartame was hydrolyzed in the gut of the monkey to its constituent moieties, methanol, aspartic acid, and phenylalanine, the ingestion of 15 or 60 mg/kg doses for 10 days did not modify phenylalanine metabolism. Aspartame had little effect on the disappearance of iv admin (14)C-phenylalanine from the plasma, it did not substantially affect the conversion of phenylalanine into tyrosine or carbon dioxide, and it did not alter the rate of incorporation of label into protein. The majority of phenylalanine derived from aspartame was incorporated into body protein, with only 20-25% of the compound being excreted. 60-80% of the derived methanol and aspartic acid was oxidized to carbon dioxide.

PMID:4200873 Oppermann JA et al; J Nutr 103 (10): 1460-6 (1973)


For more Metabolism/Metabolites (Complete) data for Aspartame (7 total), please visit the HSDB record page.


5.5 Biological Half-Life

At room temperature, aspartame is most stable at pH 4.3, where its half-life is nearly 300 days. At pH 7, its half-life is shortened to only a few days.


5.6 Mechanism of Action

180 to 200 times sweeter than sucrose, it is metabolized as a protein and its subsequent amino-acids used up in there respective mechanisms.


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NO. HA24FA503-04668HJ","address":"PLOT NO. C-58 RAMNAGAR,KALIABID","city":"BHAVNAGAR,GUJARAT","supplier":"A.H.A INTERNATIONAL","supplierCountry":"CHINA","foreign_port":"QINGDAO","customer":"HEXAGON INGREDIENTS","customerCountry":"INDIA","quantity":"750.00","actualQuantity":"750","unit":"KGS","unitRateFc":"9.8","totalValueFC":"7415.6","currency":"USD","unitRateINR":"830.8","date":"24-Oct-2024","totalValueINR":"623108.25","totalValueInUsd":"7415.6","indian_port":"Mundra","hs_no":"29242990","bill_no":"6300424","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"QINGDAO","supplierAddress":"JINAN MANSION, 306 TUNXI ROAD, HEFEI, ANHUI, CHINA CN","customerAddress":"PLOT NO. C-58 RAMNAGAR,KALIABID"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q4","strtotime":1729708200,"product":"ASPARTAME SUPER FINE POWDER - [60 DRUMS] OTHER DETAILS AS PER INVOICE & PACKING LIST - IN NO. 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04-Jan-2021
29-Oct-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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(USD/KGS)
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