DL-Aspartic acid
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DL-Aspartic acid

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Category
DL-Amino Acids
Catalog number
BAT-003582
CAS number
617-45-8
Molecular Formula
C4H7NO4
Molecular Weight
133.10
DL-Aspartic acid
IUPAC Name
2-aminobutanedioic acid
Synonyms
DL-Asp-OH; (RS)-2-Aminosuccinic acid; Aspartic acid; Aspartic acid, DL-; (RS)-Aspartic acid; (±)-Aspartic acid; 2-Azaniumyl-4-hydroxy-4-oxobutanoate; DL-Aminosuccinic acid; Aminosuccinic acid; NSC 141379
Related CAS
56-84-8 (L-isomer) 1783-96-6 (D-isomer) 874742-68-4 (Deleted CAS)
Appearance
White crystalline powder
Purity
≥95%
Density
1.663 g/cm3
Melting Point
275°C
Boiling Point
264.1±30.0°C at 760 Torr
Storage
Store at RT
Solubility
Soluble in Water
InChI
InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)
InChI Key
CKLJMWTZIZZHCS-UHFFFAOYSA-N
Canonical SMILES
C(C(C(=O)O)N)C(=O)O

DL-Aspartic acid is a non-essential amino acid that plays a critical role in various biochemical processes. Chemically, it is an isomer of aspartic acid, which is a naturally occurring amino acid. DL-Aspartic acid consists of both the L-form and D-form of aspartic acid. The L-form is the one commonly found in proteins and biological systems, while the D-form is less prevalent but still significant in certain biochemical contexts. This amino acid is integral to the biosynthesis of other amino acids and neurotransmitters, influencing cellular metabolism and signaling pathways.

One of the primary industrial applications of DL-Aspartic acid is in the production of pharmaceuticals. It is used as an intermediate in the synthesis of various drugs, including those that treat neurological disorders and other medical conditions. The compound's role in neurotransmitter synthesis makes it valuable for developing treatments that target cognitive and mood-related disorders. The pharmaceutical industry leverages DL-Aspartic acid to enhance the efficacy and specificity of certain medications.

Another significant application is in the food and beverage industry. DL-Aspartic acid serves as a flavor enhancer and a nutritional supplement in various food products. It is utilized to improve the taste and nutritional profile of processed foods, including dietary supplements and health products. By contributing to the amino acid profile of these products, DL-Aspartic acid supports both flavor enhancement and nutritional value.

In agriculture, DL-Aspartic acid is employed as a growth regulator and a component of certain fertilizers. It assists in improving plant growth and development by influencing amino acid metabolism and stress responses in plants. This application is crucial for enhancing crop yields and ensuring sustainable agricultural practices. The use of DL-Aspartic acid in fertilizers helps optimize plant health and productivity.

Finally, DL-Aspartic acid finds use in the production of various polymers and resins. It is involved in the synthesis of certain polyamides and epoxy resins, contributing to the development of high-performance materials with specific properties. These materials are used in a range of applications, including coatings, adhesives, and composite materials. The incorporation of DL-Aspartic acid in polymer chemistry enables the creation of advanced materials with desirable characteristics.

1. N-methyl-DL-aspartic acid monohydrate
D Madsen, P Pattison Acta Crystallogr C. 2000 Sep;56 ( Pt 9):1157-8. doi: 10.1107/s0108270100008593.
The title compound, C(5)H(9)NO(4).H(2)O, has been synthesized and crystallized. It crystallizes in Cc with one molecule in the asymmetric unit. The compound is found in its zwitterionic form. D and L forms of the compound are linked in the crystal via O-H...O and N-H.O hydrogen bonds, both directly between the aspartic acid-derivative entities and to the crystal water molecule. A weak intramolecular N-H...O interaction is found. The carbon skeleton is slightly twisted with C-C-C-C = 166.83 (11) degrees. A comparison with other derivatives of aspartic acid shows only two rotamers--one with a near planar carbon skeleton and one with a significantly twisted carbon skeleton.
2. DL-Aspartic acid administration improves semen quality in rabbit bucks
G Macchia, E Topo, N Mangano, E D'Aniello, R Boni Anim Reprod Sci. 2010 Apr;118(2-4):337-43. doi: 10.1016/j.anireprosci.2009.07.009. Epub 2009 Jul 30.
Recently, D-aspartic acid (d-Asp) has been suggested as being involved in mechanisms regulating reproduction activity in animals and human. In this study we analyzed the effects of DL-Asp oral administration on sperm production in the rabbit. Bucks from 60, bred in a genetic centre and used for semen production, were divided in 2 subgroups of 6 individuals. The treated group was fed with a concentrate containing DL-Asp which assured a daily administration of 1.3g dl-Asp/head; the control group was fed with the same concentrate without DL-Asp. The treatment was carried out for 2wk and animals were monitored weekly, from 1wk before the start of the treatment to 3wk after the end of the treatment. Through the experimental period there were no significant variations in semen volume between the two groups. A significant increase in both sperm concentration and kinetic parameters, i.e., the overall percentage of motile spermatozoa, the average path velocity, the percentage of progressively motile spermatozoa, etc., was found in the supplemented group. L-Asp values in blood serum and seminal plasma did not vary through the experimental period. D-Asp concentration in blood serum increased more than 4-fold than baseline (P<0.01) at the end of the treatment and was maintained at higher than baseline values for up to 3wk after the end of the treatment. D-Asp concentration in seminal plasma was higher than in blood serum before the start of the treatment (13.7+/-1.6nM vs 3.5+/-3.3nM; P<0.01) which suggests an elective storage of D-Asp in the male genital tract. Baseline values of d-Asp concentration in seminal plasma significantly increased following treatment and were back to initial values 1wk after the end of the treatment. In conclusion, DL-Asp administration improved sperm quality in bucks and the high D-Asp content in seminal plasma suggests a primary role for this D-amino acid in regulatory mechanisms of reproductive activity.
3. Methods for syntheses of N-methyl-DL-aspartic acid derivatives
M Boros, J Kökösi, J Vámos, I Kövesdi, B Noszál Amino Acids. 2007 Nov;33(4):709-17. doi: 10.1007/s00726-006-0453-4. Epub 2007 Mar 2.
A novel practical method for the synthesis of N-methyl-DL-aspartic acid 1 (NMA) and new syntheses for N-methyl-aspartic acid derivatives are described. NMA 1, the natural amino acid was synthesized by Michael addition of methylamine to dimethyl fumarate 5. Fumaric or maleic acid mono-ester and -amide were regioselectively transformed into beta-substituted aspartic acid derivatives. In the cases of maleamic 11a or fumaramic esters 11b, the alpha-amide derivative 13 was formed, but hydrolysis of the product provided N-methyl-DL-asparagine 9 via base catalyzed ring closure to DL-alpha-methylamino-succinimide 4, followed by selective ring opening. Efficient methods were developed for the preparation of NMA-alpha-amide 13 from unprotected NMA via sulphinamide anhydride 15 and aspartic anhydride 3 intermediate products. NMA diamide 16 was prepared from NMA dimethyl ester 6 and methylamino-succinimide 4 by ammonolysis. Temperature-dependent side reactions of methylamino-succinimide 4 led to diazocinone 18, resulted from self-condensation of methylamino-succinimide via nucleophyl ring opening and the subsequent ring-transformation.
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