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Chemistry

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Also known as: L-aspartic acid, 56-84-8, H-asp-oh, Asparagic acid, (2s)-2-aminobutanedioic acid, L-aspartate
Molecular Formula
C4H7NO4
Molecular Weight
133.10  g/mol
InChI Key
CKLJMWTZIZZHCS-REOHCLBHSA-N
FDA UNII
30KYC7MIAI

Aspartic Acid API
One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.
1 2D Structure

Aspartic Acid API

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-2-aminobutanedioic acid
2.1.2 InChI
InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)/t2-/m0/s1
2.1.3 InChI Key
CKLJMWTZIZZHCS-REOHCLBHSA-N
2.1.4 Canonical SMILES
C(C(C(=O)O)N)C(=O)O
2.1.5 Isomeric SMILES
C([C@@H](C(=O)O)N)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
30KYC7MIAI
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (+-)-aspartic Acid

2. (r,s)-aspartic Acid

3. Ammonium Aspartate

4. Aspartate

5. Aspartate Magnesium Hydrochloride

6. Aspartate, Ammonium

7. Aspartate, Calcium

8. Aspartate, Dipotassium

9. Aspartate, Disodium

10. Aspartate, Magnesium

11. Aspartate, Monopotassium

12. Aspartate, Monosodium

13. Aspartate, Potassium

14. Aspartate, Sodium

15. Aspartic Acid, Ammonium Salt

16. Aspartic Acid, Calcium Salt

17. Aspartic Acid, Dipotassium Salt

18. Aspartic Acid, Disodium Salt

19. Aspartic Acid, Hydrobromide

20. Aspartic Acid, Hydrochloride

21. Aspartic Acid, Magnesium (1:1) Salt, Hydrochloride, Trihydrate

22. Aspartic Acid, Magnesium (2:1) Salt

23. Aspartic Acid, Magnesium-potassium (2:1:2) Salt

24. Aspartic Acid, Monopotassium Salt

25. Aspartic Acid, Monosodium Salt

26. Aspartic Acid, Potassium Salt

27. Aspartic Acid, Sodium Salt

28. Calcium Aspartate

29. Dipotassium Aspartate

30. Disodium Aspartate

31. L Aspartate

32. L Aspartic Acid

33. L-aspartate

34. L-aspartic Acid

35. Magnesiocard

36. Magnesium Aspartate

37. Mg-5-longoral

38. Monopotassium Aspartate

39. Monosodium Aspartate

40. Potassium Aspartate

41. Sodium Aspartate

2.3.2 Depositor-Supplied Synonyms

1. L-aspartic Acid

2. 56-84-8

3. H-asp-oh

4. Asparagic Acid

5. (2s)-2-aminobutanedioic Acid

6. L-aspartate

7. Aspartate

8. Aspatofort

9. (s)-2-aminosuccinic Acid

10. L-asparagic Acid

11. L-aminosuccinic Acid

12. Asparaginic Acid

13. L-asparaginic Acid

14. (s)-aspartic Acid

15. (2s)-aspartic Acid

16. (s)-aminobutanedioic Acid

17. Aspartic Acid, L-

18. L-aspartinsaeure

19. L-asparaginsaeure

20. L-asparaginsyra

21. Acidum Asparticum

22. L-(+)-aspartic Acid

23. L-asp

24. L-2-aminobutanedioic Acid

25. 25608-40-6

26. Aspartate, L-

27. Asparaginsaeure [german]

28. Aminosuccinic Acid

29. Butanedioic Acid, Amino-, (s)-

30. Aspartic Acid (van)

31. Asparagic Acid (van)

32. (s)-(+)-aminosuccinic Acid

33. Asparaginic Acid (van)

34. Acide Aspartique [inn-french]

35. Acido Aspartico [inn-spanish]

36. (l)-aspartic Acid

37. (+)-aspartic Acid

38. Fema No. 3565

39. Ccris 6181

40. Acidum Asparticum [inn-latin]

41. Hsdb 1430

42. L( )-aminobernsteinsaeure

43. Ai3-04461

44. Poly-l-aspartate

45. L-aspartic Acid Homopolymer

46. Nsc 3973

47. 6899-03-2

48. 2-aminosuccinic Acid

49. Deamidated Asparagine

50. Brn 1723530

51. Beta-l-aspartic Acid

52. Chebi:17053

53. Mfcd00002616

54. 30kyc7miai

55. Asp

56. (s)-(+)-aspartic Acid

57. (s)-2-aminobutanedioic Acid

58. Chembl274323

59. Fema No. 3656

60. Asparaginsaeure

61. (s)-aspartate

62. L-asparticacid

63. (+)-aspartate

64. Polyaspartic Acid

65. L-aspartic Acid-13c4

66. 1-amino-1,2-carboxyethane

67. (s)-aminobutanedioate

68. L(+)-aspartic Acid

69. 55443-54-4

70. Acido Aspartico

71. Acide Aspartique

72. Aspartic Acid [usan:inn]

73. (s)-aminosuccinic Acid

74. 4-04-00-02998 (beilstein Handbook Reference)

75. 39162-75-9

76. Einecs 200-291-6

77. Unii-30kyc7miai

78. L(+)-aminobernsteinsaeure

79. Aminosuccinate

80. Asparagate

81. Asparatate

82. L-aspartic Acid, Homopolymer

83. Nsc-3973

84. Aspartic Acid,l

85. L-aspartic-acid

86. L-asparagate

87. L-aminosuccinate

88. Aspartic Acid [usan:usp:inn]

89. (l)-aspartate

90. L- Aspartic Acid

91. Alpha-aminosuccinate

92. (2s)-aspartate

93. Poly-l-asparticacid

94. L-(+)-aspartate

95. [3h]-l-aspartate

96. L-[14c]aspartate

97. L-aspartic Acid, 2

98. [3h]l-aspartic Acid

99. (r)-2-aminosuccinate

100. (s)-2-aminosuccinate

101. Tocris-0214

102. [3h]-l-asp

103. (s)-amino-butanedioate

104. Alpha-aminosuccinic Acid

105. (s)-(+)-aspartate

106. [3h]-l-aspartic Acid

107. L-aspartic Acid (9ci)

108. 2-amino-3-methylsuccinate

109. Biomol-nt_000168

110. Bmse000031

111. Bmse000875

112. Aspartic Acid (usp/inn)

113. Ec 200-291-6

114. Aspartic Acid [ii]

115. Aspartic Acid [mi]

116. L-aspartic Acid (jp17)

117. Schembl3231

118. (s)-amino-butanedioic Acid

119. Aspartic Acid [inn]

120. L-aspartic Acid-[13c4]

121. L-aspartic Acid, >=98%

122. L-aspartic Acid, 99.0%

123. Lopac0_000133

124. Aspartic Acid [hsdb]

125. Aspartic Acid [inci]

126. Aspartic Acid [usan]

127. Aspartic Acid, L- (8ci)

128. Aspartic Acid [vandf]

129. Aspartic Acid [mart.]

130. L-aspartic Acid (h-asp-oh)

131. L-aspartic Acid [fcc]

132. L-aspartic Acid [jan]

133. (2s)-2-azanylbutanedioic Acid

134. Bpbio1_001128

135. Gtpl3309

136. Gtpl4534

137. Aspartic Acid [usp-rs]

138. Aspartic Acid [who-dd]

139. L-aspartic Acid [fhfi]

140. Dtxsid7022621

141. Aspartic Acid (l-aspartic Acid)

142. Bdbm18125

143. L-aspartic Acid, >=98%, Fg

144. Hms3260k08

145. Zinc895032

146. .alpha.-aminosuccinic Acid, (l)-

147. Aspartic Acid [ep Impurity]

148. Hy-n0666

149. Str04614

150. Tox21_500133

151. Aspartic Acid [ep Monograph]

152. Pdsp1_000819

153. Pdsp2_000806

154. Aspartic Acid [usp Monograph]

155. Akos006239578

156. Akos015853957

157. Am81585

158. Ccg-204228

159. Db00128

160. Lp00133

161. Sdccgsbi-0050121.p002

162. Alanine Impurity A [ep Impurity]

163. L-aspartic Acid (h-asp-oh) Usp Grade

164. Ncgc00024499-01

165. Ncgc00024499-02

166. Ncgc00024499-03

167. Ncgc00024499-04

168. Ncgc00024499-05

169. Ncgc00024499-06

170. Ncgc00024499-10

171. Ncgc00260818-01

172. Bp-13291

173. L-aspartic Acid, Vetec(tm) Reagent Grade

174. Db-029944

175. A0546

176. Cs-0009701

177. Eu-0100133

178. L-aspartic Acid, Bioxtra, >=99% (hplc)

179. S5632

180. L-aspartic Acid, Bioultra, >=99.5% (t)

181. A 9256

182. A-9220

183. C00049

184. D00013

185. D70832

186. Lysine Acetate Impurity A [ep Impurity]

187. M03000

188. L-aspartic Acid, Saj Special Grade, >=99.0%

189. A817928

190. A824434

191. L-aspartic Acid, Reagent Grade, >=98% (hplc)

192. Q178450

193. Sr-01000597734

194. Sr-01000597734-3

195. F8889-8684

196. Z1270403519

197. A4b5fb11-a4b6-4d75-9860-2acf670700b9

198. Aspartic Acid, European Pharmacopoeia (ep) Reference Standard

199. L-aspartic Acid, Certified Reference Material, Tracecert(r)

200. Aspartic Acid, United States Pharmacopeia (usp) Reference Standard

201. L-aspartic Acid, Bioreagent, Suitable For Cell Culture, Suitable For Insect Cell Culture

202. L-aspartic Acid, Pharmaceutical Secondary Standard; Certified Reference Material

203. L-aspartic Acid, From Non-animal Source, Meets Ep, Usp Testing Specifications, Suitable For Cell Culture, 98.5-101.0%

204. L-aspartic Acid, Pharmagrade, Ajinomoto, Ep, Jp, Usp, Manufactured Under Appropriate Gmp Controls For Pharma Or Biopharmaceutical Production, Suitable For Cell Culture

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 133.10 g/mol
Molecular Formula C4H7NO4
XLogP3-2.8
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Exact Mass133.03750770 g/mol
Monoisotopic Mass133.03750770 g/mol
Topological Polar Surface Area101 Ų
Heavy Atom Count9
Formal Charge0
Complexity133
Isotope Atom Count0
Defined Atom Stereocenter Count1
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

MEDICATION (VET): TO REDUCE AMMONIA BLOOD LEVELS & SAID TO BE OF VALUE IN OVERCOMING FATIGUE. ... DOSAGE: GIVEN ORALLY OR AS FEED ADDITIVE AGAINST STRESS INDUCED HIGH BLOOD AMMONIA LEVELS IN POULTRY & AGAINST AMMONIA INTOXICATED RATS. /ASPARTIC ACID/

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 28


Parenteral nutrition

Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present., p. VA2 84


/EXPL/: L-aspartate is a glycogenic amino acid, and it can also promote energy production via its metabolism in the Krebs cycle. These latter activities were the rationale for the claim that supplemental aspartate has an anti-fatigue effect on skeletal muscle, a claim that was never confirmed. /L-aspartate/

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ (2001) p.255


There are claims that L-aspartate is a special type of mineral transporter for cations, such as magnesium, into cells. Magnesium aspartate has not been found to be more biologically effective when compared with other magnesium salts. There are also claims that L-aspartate has ergogenic effects, that it enhances performance in both prolonged exercise and short intensive exercise. It is hypothesized that L-aspartate, especially the potassium magnesium aspartate salt, spares stores of muscle glycogen and/or promotes a faster rate of glycogen resynthesis during exercise. It has also been hypothesized that L-aspartate can enhance short intensive exercise by serving as a substrate for energy production in the Krebs cycle and for stimulating the purine nucleotide cycle. An animal study using injected aspartate failed to find any evidence of a glycogen-sparing effect or any ergogenic effects whatsoever. A more recent double-blind human study of male weight trainers similarly found aspartate supplementation to have no effect, and another study of the effect of aspartate on short intensive exercise again found no effect. /L-aspartate/

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ (2001) p.254


For more Therapeutic Uses (Complete) data for (L)-ASPARTIC ACID (6 total), please visit the HSDB record page.


4.2 Drug Warning

Mild gastrointestinal side effects including diarrhea have been reported. /L-aspartate/

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ (2001) p.255


Because of lack of long-term safety studies, L-aspartate salts should be avoided by children, pregnant women and lactating women. /L-Aspartate/

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ (2001) p.255


The effects of oral administration of potassium and magnesium aspartate (K + Mg Asp) on physiologic responses to 90 min of treadmill walking at approximately 62% VO2 max were evaluated in seven healthy males (VO2 max = 59.5 ml X kg-1 X min-1). A total of 7.2 g of K + Mg Asp were administered to each subject during a 24 h period prior to work and compared to control and placebo trials. For control, placebo, and K + Mg Asp trials, no significant differences were observed in resting or exercise values for ventilation (VE), oxygen uptake (VO2), carbon dioxide production (VCO2), respiratory exchange ratio (RO), heart rate (HR), or blood pressure (BP). In addition, there were no differences between the three trials for exercise-induced decreases in body weight and increases in rectal temperature, or for pre- and post-exercise alterations in serum lactic acid, creatine kinase, lactic dehydrogenase, and percentage change in plasma volume. The findings from this study indicate that oral ingestion of K+ Mg Asp prior to exercise had no effect on cardiorespiratory, hematologic, and metabolic responses to 90 min of work conducted at approximately 62% VO2 max. /Potassium magnesium aspartate/

PMID:7138632 Hagan RD et al; Int J Sports Med 3 (3): 177-81 (1982)


This study examined the effects of aspartate supplementation (ASP) on plasma ammonia concentrations (NH4+) during and after a resistance training workout (RTW). Twelve male weight trainers were randomly administered ASP or vitamin C in a crossover, double blind protocol, each trial separated by 1 wk. ASP and vitamin C were given over a 2 hr period beginning 5 hr prior to the RTW. The RTW consisted of bench, incline, shoulder, and triceps presses, and biceps curls at 70% of one repetition maximum (1-RM). After the RTW a bench press test (BPT) to failure at 65% of 1-RM was used to assess performance. (NH4+) was determined preexercise, 20 and 40 min midworkout, immediately postexercise, and 15 min postexercise. Treatment-by-time ANOVAs, paired t tests, and contrast comparisons were used to identify mean differences. No significant differences were observed between treatments for (NH4+) or BPT. (NH4+) increased significantly from Pre to immediately postexercise for both the ASP and vitamin C trials. Acute ASP supplementation does not reduce (NH4+) during and after a high intensity RTW in weight trained subjects. /Potassium magnesium aspartate/

PMID:7670449 Tuttle JL et al; Int J Sport Nutr 5 (2): 102-9 (1995)


4.3 Drug Indication

There is no support for the claim that aspartates are exercise performance enhancers, i.e. ergogenic aids.


5 Pharmacology and Biochemistry
5.1 Pharmacology

L-aspartate is considered a non-essential amino acid, meaning that, under normal physiological conditions, sufficient amounts of the amino acid are synthesized in the body to meet the body's requirements. L-aspartate is formed by the transamination of the Krebs cycle intermediate oxaloacetate. The amino acid serves as a precursor for synthesis of proteins, oligopeptides, purines, pyrimidines, nucleic acids and L-arginine. L-aspartate is a glycogenic amino acid, and it can also promote energy production via its metabolism in the Krebs cycle. These latter activities were the rationale for the claim that supplemental aspartate has an anti-fatigue effect on skeletal muscle, a claim that was never confirmed.


5.2 Absorption, Distribution and Excretion

Absorption

Absorbed from the small intestine by an active transport process


ASPARTIC ACID PLASMA CONCN WAS ELEVATED 30 MIN AFTER 1 G/KG L-ASPARTATE (ORAL OR IP) TO 15 DAY OLD & ADULT MICE. THEREAFTER, CONCN DECLINED EXPONENTIALLY WITH T/2 OF 0.2 HR IN BOTH. PLASMA CONCN NOT APPRECIABLY ALTERED BY 10 & 100 MG/KG L-ASPARTATE ORAL OR IP ADMIN.

OPPERMANN ET AL; J ENVIRON PATHOL TOXICOL 2(4) 987 (1979)


Following ingestion, L-aspartate is absorbed from the small intestine by an active transport process. Following absorption, L-aspartate enters the portal circulation and from there is transported to the liver, where much of it is metabolized to protein, purines, pyrimidines and L-arginine, and is catabolized as well. L-aspartate is not metabolized in the liver; it enters the systemic circulation, which distributes it to various tissues of the body. The cations associated with L-aspartate independently interact with various substances in the body and participate in various physiological processes. /L-aspartate/

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ (2001) p.254


... Contents of D- and L-aspartic acids in rats at different stages of growth (from 1 day before birth to 90 days after birth) were determined. D-Aspartic acid was detected in all the brain tissue samples tested, but at different levels. In the cerebrum of rats 1 day before birth, D-aspartic acid was found to be at the highest concentration of 81 nmol/g wet tissue. The level of D-aspartic acid in rat brain falls rapidly after birth, while the L-aspartic acid level increases with age.

PMID:11589464 Zhao S et al; J Chromatogr B Biomed Sci Appl 762 (1): 97-101 (2001)


Enzymatic synthesis of 11C-(4)-L-aspartic acid was undertaken using commercially available wheat germ phosphoenolpyruvate carboxylase. Whole-body distribution of the radioactive compound in rats showed higher accumulation in the salivary gland, glandular stomach and the pancreas, as well as in the lungs. Within 60 minutes after intravenous injection of 11C-(4)-L-aspartic acid, about 60% is removed as 11CO2 by expiration, indicating that the carbon atom at the fourth position of the radioactive compound is easily subjected to decarboxylation.

PMID:6494491 Nakamura T et al; Radioisotopes 33 (6): 363-9 (1984)


The brain efflux index method has been used to clarify the mechanism of efflux transport of acidic amino acids such as L-aspartic acid (L-Asp), L-glutamic acid (L-Glu), and D-aspartic acid (D-Asp) across the blood-brain barrier (BBB). About 85% of L-[3H]Asp and 40% of L-(3H)Glu was eliminated from the ipsilateral cerebrum within, respectively, 10 and 20 min of microinjection into the brain. The efflux rate constant of L-(3H)Asp and L-(3H)Glu was 0.207 and 0.0346 min(-1), respectively. However, D-(3H)Asp was not eliminated from brain over a 20-min period. The efflux of L-(3H)Asp and L-(3H)Glu was inhibited in the presence of excess unlabeled L-Asp and L-Glu, whereas D-Asp did not inhibit either form of efflux transport. Aspartic acid efflux across the BBB appears to be stereospecific. Using a combination of TLC and the bioimaging analysis, attempts were made to detect the metabolites of L-(3H)Asp and L-(3H)Glu in the ipsilateral cerebrum and jugular vein plasma following a microinjection into parietal cortex, area 2. Significant amounts of intact L-(3H)Asp and L-(3H)Glu were found in all samples examined, including jugular vein plasma, providing direct evidence that at least a part of the L-Asp and L-Glu in the brain interstitial fluid is transported across the BBB in the intact form. To compare the transport of acidic amino acids using brain parenchymal cells, brain slice uptake studies were performed. Although the slice-to-medium ratio of D-(3H)Asp was the highest, followed by L-[3H]Glu and L-[3H]Asp, the initial uptake rate did not differ for both L-(3H)Asp and D-(3H)Asp, suggesting that the uptake of aspartic acid in brain parenchymal cells is not stereospecific. These results provide evidence that the BBB may act as an efflux pump for L-Asp and L-Glu to reduce the brain interstitial fluid concentration and act as a static wall for D-Asp.

PMID:10461913 Hosoya K et al; J Neurochem 73 (3): 1206-11 (1999)


5.3 Metabolism/Metabolites

FOR L-ASPARTIC ACID, OXALOACETIC ACID IS PRODUCT OF OXIDATIVE DEAMINATION OR TRANSAMINATION; ALPHA-ALANINE IS PRODUCT OF DECARBOXYLATION. /FROM TABLE/

Fenaroli's Handbook of Flavor Ingredients. Volume 2. Edited, translated, and revised by T.E. Furia and N. Bellanca. 2nd ed. Cleveland: The Chemical Rubber Co., 1975., p. 829


METABOLIC PATHWAYS & PRODUCTS /IN ANIMAL BODY/: ASPARTIC ACID + CARBAMYLPHOSPHATE /PRODUCE/ PHOSPHORUS + CARBAMYLASPARTIC ACID GIVE PYRIMIDINES; ASPARTIC ACID /PRODUCES/ FUMARIC ACID + NH3; ASPARTIC ACID /PRODUCES/ ASPARTIC SEMIALDEHYDE /PRODUCES/ HOMOSERINE /PRODUCES/ (I) THREONINE, (II) METHIONINE, OR (III) LYSINE... /FROM TABLE/

Fenaroli's Handbook of Flavor Ingredients. Volume 2. Edited, translated, and revised by T.E. Furia and N. Bellanca. 2nd ed. Cleveland: The Chemical Rubber Co., 1975., p. 829


METABOLIC PATHWAYS & PRODUCTS /IN ANIMAL BODY/: ASPARTIC ACID GIVES NITROGEN OF PURINE RING...ASPARTIC ACID + IMP GIVE ADENYLOSUCCINATE GIVES AMP + FUMARATE... /FROM TABLE/

Fenaroli's Handbook of Flavor Ingredients. Volume 2. Edited, translated, and revised by T.E. Furia and N. Bellanca. 2nd ed. Cleveland: The Chemical Rubber Co., 1975., p. 829


Following ingestion, L-aspartate is absorbed from the small intestine by an active transport process. Following absorption, L-aspartate enters the portal circulation and from there is transported to the liver, where much of it is metabolized to protein, purines, pyrimidines and L-arginine, and is catabolized as well. D-aspartate is not metabolized in the liver; it enters the systemic circulation, which distributes it to various tissues of the body. The cations associated with L-aspartate independently interact with various substances in the body and participate in various physiological processes. /L-aspartate; D-aspartate/

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ (2001) p.254


5.4 Mechanism of Action

There are also claims that L-aspartate has ergogenic effects, that it enhances performance in both prolonged exercise and short intensive exercise. It is hypothesized that L-aspartate, especially the potassium magnesium aspartate salt, spares stores of muscle glycogen and/or promotes a faster rate of glycogen resynthesis during exercise. It has also been hypothesized that L-aspartate can enhance short intensive exercise by serving as a substrate for energy production in the Krebs cycle and for stimulating the purine nucleotide cycle.


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