Basic information
- CAS
997-55-7- Standard SMILES
CC(=O)N[C@@H](CC(=O)O)C(=O)O- InChIKey
OTCCIMWXFLJLIA-BYPYZUCNSA-N- Molecular formula
- C6H9NO5
- Average molar mass
- 175.14 g/mol
- Monoisotopic mass
- 175.04807239
Overview
N-acetyl-L-aspartic acid is an N-acyl-L-aspartic acid in which the acyl group is specified as acetyl. It has a role as an antioxidant, a nutraceutical, a mouse metabolite, a human metabolite and a rat metabolite. It is a N-acetyl-L-amino acid and a N-acyl-L-aspartic acid. It is a conjugate acid of a N-acetyl-L-aspartate(2-).
Names & identifiers
- Preferred name
- N-Acetyl-L-Aspartic Acid
- IUPAC
- (2S)-2-acetamidobutanedioic acid
- English name
- N-Acetyl-L-aspartic acid
- Molecular formula
- C6H9NO5
- Molecular weight
- 175.14
Names & synonyms
N-Acetyl-L-aspartic acid997-55-7Acetyl-L-aspartic acidN-Acetylaspartate(2S)-2-acetamidobutanedioic acidAcetylaspartic acidL-Aspartic acid, N-acetyl-L-N-Acetylaspartic acidAcetyl aspartic acidN-acetyl-s-aspartic acid(S)-2-(acetylamino)butanedioic acidAspartic acid, N-acetyl-, L-
Show more names
AC-ASP-OHAc-L-Asp-OHn-acetylasparticacidn-acetyl-l-asparticaciN-AC-L-ASPD4001Ac-Asp-OhacetylasparticacidN-Acetyl-L-aspartic
DTXSID40897219(S)-2-(acetylamino)succinic acid445Y04YIWRCHEBI:21547NSC-128610n-acetyl aspartateAcetylaspartatic AcidN-Acetylaspartatic Acid
Database identifiers
- CAS
997-55-7- PubChem CID
- 65065
- DTXSID
DTXSID40897219
Properties
Computed structural properties
- XLogP
- -1.1
- Topological polar surface area
- 104 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 212
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Amino Acids and Derivatives
Solubility
675 mg/mL
>26.3 [ug/mL] (The mean of the results at pH 7.4)
Melting Point137 - 140 °C
Physical Description
White odorless powder; [Acros Organics MSDS]
Solid
Collision Cross Section
131 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
143.7 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]
129.21 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
139.3 Ų [M+Na]+
Physicochemical properties
- Melting point
- 137 · 137-140 °C(lit.)
- alpha
- 52 · 52 º (c=1, HAc)
- Boiling point
- 425.3 · 425.3±35.0 °C(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 5 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazards SummaryCauses excitement and alteration of classical conditioning in acute intraperitoneal studies of rats; [RTECS] May cause irritation; [Acros Organics MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Toxicology
Health EffectsChronically high levels of N-acetyl-aspartate are associated with Canavan Disease.
Toxicity Summary
The primary proposed functions of N-acetylaspartic acid include: 1) A neuronal osmolyte that is involved in fluid balance in the brain; 2) a source of acetate for lipid and myelin synthesis in oligodendrocytes, the glial cells that myelinate neuronal axons; 3) a precursor for the synthesis of the important neuronal dipeptide N-acetylaspartylglutamate; 4) N-acetylaspartic acid may also be involved in energy production from the amino acid glutamate in neuronal mitochondria. Excess amounts of N-acetyl-L-aspartic acid accumulated in plasma, spinal fluid, and urine have been found to be toxic. On the other hand, decreased concentration of N-acetyl-L-aspartic acid according to the in vivo spectrum of the brain has been related to disorders such as hypoacetylaspartia.
Chemistry & industry
Pharmacology
Tissue LocationsBasal Ganglia
Cellular LocationsCytoplasm
Metabolite PathwaysAspartate Metabolism
Uses & manufacturing
Uses
Amino acid found in the nervous system; [Merck Index]
This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Applications
UsesN-Acetyl-L-aspartic acid can be used as a reactant to synthesize: Protected homoserine γ-lactones by selective reduction and acid-catalyzed cyclization reaction.Racemic amino substituted succinimide derivatives via cyclocondensation reaction.
UsesN-Acetyl-L-aspartic acid is used in biological studies for metabolic alterations associated with schizophrenia.
UsesNutritional supplement; in forensic determination of age.
Upstream & downstream products
Upstream raw materials
Related reactions
2 records
Compound notes
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