(2S)-2-aminobutanedioic acid

• ChemBase ID: 14
• Molecular Formular: C4H7NO4
• Molecular Mass: 133.10268
• Monoisotopic Mass: 133.03750771
• SMILES: OC(=O)[C@@H](N)CC(=O)O
• Canonical SMILES: OC(=O)C[C@@H](C(=O)O)N
• 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
• InChIKey: CKLJMWTZIZZHCS-REOHCLBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-aminobutanedioic acid
• IUPAC Traditional name: L-aspartic acid
• Brand Name: Aspatofort
• Synonyms: L-Aspartic acid; (S)-2-Aminosuccinic acid; ASPARTIC ACID, USP GRADE; (S)-(+)-Aminosuccinic acid; (+)-Aspartic acid; (2S)-Aspartic acid; (L)-Aspartic acid; (S)-Aminobutanedioic acid; (S)-Aspartic acid; Acide aspartique [INN-French]; Acido aspartico [INN-Spanish]; Acidum asparticum; Aminosuccinic acid; Asparagic acid; Asparaginic acid; Asparaginsaeure [German]; Aspartate; Aspartic acid; H-Asp-OH; L-(+)-Aspartic acid; L-2-Aminobutanedioic acid; L-Aminosuccinic acid; L-Asparagic acid; L-Asparaginic acid; L-Asparaginsaeure; L-Asparaginsyra; L-Aspartinsaeure; L-Aspartic Acid; (S)-(+)-氨基琥珀酸; (S)-氨基丁二酸; L-天冬氨酸; 天冬氨酸; L-天门冬氨酸

Database IDs

• CAS Number: 6899-03-2; 56-84-8
• EC Number: 200-291-6
• MDL Number: MFCD00002616
• Beilstein Number: 1723530
• Merck Index: 14840
• PubChem SID: 24890873; 46507997; 24891191; 160963477; 24890976; 24891385; 24277948; 24847046
• PubChem CID: 5960
• FEMA ID: 3656
• Flavis Number: 17.005

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.7025436
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -4.018386
• LogD (pH = 7.4): -5.749634
• Log P: -3.5037527
• Molar Refractivity: 26.5327 cm^3
• Polarizability: 10.896484 Å^3
• Polar Surface Area: 100.62 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -3.52
• LOG S: 0.03
• Solubility (Water): 1.42e+02 g/l

PROPERTIES

Physical Property

• Solubility: 0.5 M HCl: soluble50 mg/mL (with heat); 1 M HCl: soluble0.5 M at 20 °C, clear, colorless; 1 M HCl: soluble100 mg/mL; 1 M HCl: soluble50 mg/mL; 1 M NaOH: soluble50 mg/mL; 4.5 g/l; H2O: soluble5 mg/mL
• Apperance: powder; Powder
• Melting Point: >300 °C (dec.)(lit.); >300°C dec.; 270-271; 270-271°C
• Density: 1.66
• Optical Rotation: [α]/D 24.0 to 26.0°, c = 8 in hydrochloric acid (6 N HCl); [α]20/D +24.7±1°, c = 5% in 5 M HCl; [α]20/D +25°, c = 8 in 5 M HCl; +25 (c=2 in 5N HCl)
• Absorption Wavelength: λ: 260 nm Amax: 0.20; λ: 280 nm Amax: 0.10
• Hydrophobicity(logP): -3.7

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• RTECS: CI9098500
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 36
• Safety Statements: 26
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 20-25°C

Pharmacology Properties

• Gene Information: human ... CA1(759), CA2(760)rat ... Grin2a(24409)

Product Information

• Purity: ≥99%; ≥98%; ≥98% (TLC); ≥98.5%; ≥99% (TLC); ≥99.0%; ≥99.0% (T); ≥99.5% (T); 98%; 98.5-101.0%; 98+%; 99%, low metals content
• Grade: certified reference material; EP; Ph Eur; PharmaGrade; reagent grade; SAJ special grade; TraceCERT®; USP
• Optical Purity: ee: 98% (GLC)
• Suitability: meets EP, USP testing specifications; suitable for cell culture; suitable for insect cell culture; suitable for manufacturing use
• Ignition Residue: ≤0.05% (as SO4); ≤0.1%; ≤0.1% (as SO4)
• Impurities: ≤0.0005% Phosphorus (P); ≤0.1% Insoluble matter; ≤0.3% foreign amino acids; endotoxin, tested; insoluble matter, passes filter test
• Cation Traces: Al: ≤0.0005%; Al: ≤5 mg/kg; As: ≤0.1 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: ≤0.001%; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤0.0005%; Cu: ≤5 mg/kg; Fe: ≤0.0005%; Fe: ≤5 mg/kg; K: ≤0.005%; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: ≤0.0005%; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤0.005%; Na: ≤100 mg/kg; Na: ≤500 mg/kg; NH4+: ≤0.05%; NH4+: ≤200 mg/kg; NH4+: ≤500 mg/kg; Ni: ≤5 mg/kg; Pb: ≤0.001%; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: ≤0.0005%; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤0.05%; chloride (Cl-): ≤50 mg/kg; sulfate (SO42-): ≤0.05%; sulfate (SO42-): ≤150 mg/kg; sulfate (SO42-): ≤300 mg/kg
• Biological Source: from non-animal source
• Loss on Drying: ≤0.1% loss on drying, 110 °C
• Quality Level: GMP-COMPENDIA; PREMIUM
• λ: 0.5 M in 1 M HCl
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Product Line: BioReagent; BioUltra; BioXtra
• Linear Formula: HO2CCH2CH(NH2)CO2H

DETAILS

MP Biomedicals - 02194633

Cell Culture Reagent
Crystalline
Purity: 99+%

MP Biomedicals - 02100809

Crystalline
Purity: >99%

DrugBank - DB00128

• Drug Groups: approved; nutraceutical
• Description: 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. [PubChem]
• Indication: There is no support for the claim that aspartates are exercise performance enhancers, i.e. ergogenic aids.
• 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.
• Toxicity: Mild gastrointestinal side effects including diarrhea. LD₅₀ (rat) > 5,000 mg/kg.
• Affected Organisms: Humans and other mammals
• Absorption: Absorbed from the small intestine by an active transport process
• External Links: Wikipedia; PDRhealth

Sigma Aldrich - A5474

Biochem/physiol Actions
Principal neurotransmitter for fast synaptic excitation.
Packaging
Manufactured and Packaged under cGMP.

Sigma Aldrich - A8949

Biochem/physiol Actions
Principal neurotransmitter for fast synaptic excitation.
L-Aspartic acid is a natural proteinogenic amino acid that may be used in the formulation of cell culture media and in protein and polypeptide synthesis systems and procedures. L-Aspartic acid, an NMDA receptor agonist and non-specific glutamate receptor agonist, is used to differentiate and study the mechanisms of NMDA receptors.
Packaging
10 mg in autosmp vl

Sigma Aldrich - A7219

Biochem/physiol Actions
Principal neurotransmitter for fast synaptic excitation.

Sigma Aldrich - 11189

Biochem/physiol Actions
Principal neurotransmitter for fast synaptic excitation.

Sigma Aldrich - A9256

Biochem/physiol Actions
Principal neurotransmitter for fast synaptic excitation.

Sigma Aldrich - A4534

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Principal neurotransmitter for fast synaptic excitation.

Sigma Aldrich - W365601

Biochem/physiol Actions
Principal neurotransmitter for fast synaptic excitation.
Packaging
1 sample in glass bottle
1, 5 kg in poly bottle

Sigma Aldrich - A93100

Biochem/physiol Actions
Principal neurotransmitter for fast synaptic excitation.
Packaging
100, 500 g in poly bottle
2 kg in poly bottle
2.5 g in glass bottle

Sigma Aldrich - 77737

Biochem/physiol Actions
Principal neurotransmitter for fast synaptic excitation.

Sigma Aldrich - 51572

Analysis Note
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34. This CRM is traceable to NIST SRM.
Biochem/physiol Actions
Principal neurotransmitter for fast synaptic excitation.
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 11190

Biochem/physiol Actions
Principal neurotransmitter for fast synaptic excitation.
L-Aspartic acid is a negatively charged carboxyl side-chain containing α amino acid. Aspartic acid is involved in nitrogen metabolism via its inter-conversion to oxaloacetate (OAA). As one of the 22 proteinogenic amino acids L-Asp is incorporated into proteins by translation processes in vitro. L-Aspartic acid is a non-essential amino acid added to cell culture media. L-aspartate supports polyamine biosynthesis.

Sigma Aldrich - 01-6810

Biochem/physiol Actions
Principal neurotransmitter for fast synaptic excitation.

REFERENCES

• Readily forms ?-lactam derivatives whichare valuable intermediates for the synthesis of a variety of products, including thienamycin: J. Am. Chem. Soc., 102, 6163 (1980); Tetrahedron Lett., 23, 2293 (1982).