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00920

Sigma-Aldrich

N-Acetyl-L-aspartic acid

≥99.0% (T)

Synonym(s):

(2S)-2-Acetamidobutanedioic acid, N-Acetyl-S-aspartic acid

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About This Item

Linear Formula:
HO2CCH2CH(NHCOCH3)CO2H
CAS Number:
Molecular Weight:
175.14
Beilstein:
1726198
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥99.0% (T)

form

powder

optical activity

[α]20/D +12±1°, c = 2% in 6 M HCl

reaction suitability

reaction type: solution phase peptide synthesis

color

colorless to white

mp

137-140 °C (lit.)
141-146 °C

application(s)

peptide synthesis

SMILES string

CC(=O)N[C@@H](CC(O)=O)C(O)=O

InChI

1S/C6H9NO5/c1-3(8)7-4(6(11)12)2-5(9)10/h4H,2H2,1H3,(H,7,8)(H,9,10)(H,11,12)/t4-/m0/s1

InChI key

OTCCIMWXFLJLIA-BYPYZUCNSA-N

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Application

N-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.

Other Notes

Review; acetyl donor in acetylcholine formation in brain.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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P Gideon et al.
Stroke, 23(11), 1566-1572 (1992-11-01)
The early time course after acute stroke of cerebral N-acetylaspartate, creatine and phosphocreatine, and compounds containing choline was studied in vivo by means of localized water-suppressed proton magnetic resonance spectroscopy. Eight patients with acute stroke were studied serially in the
Maria A Rocca et al.
NeuroImage, 18(4), 847-855 (2003-05-03)
Previous work has suggested that functional reorganization of cortical areas might have a role in limiting the clinical impact of axonal pathology in patients with established multiple sclerosis (MS). Since there is evidence for irreversible tissue damage even in patients
Emilie Chamard et al.
Neurosurgical focus, 33(6), E4: 1-E4: 7 (2012-12-04)
Despite negative neuroimaging findings using traditional neuroimaging methods such as MRI and CT, sports-related concussions have been shown to cause neurometabolic changes in both the acute and subacute phases of head injury. However, no prospective clinical study has used an
E A Kvittingen et al.
Clinica chimica acta; international journal of clinical chemistry, 158(3), 217-227 (1986-08-15)
Excessive excretion of N-acetylaspartic acid in urine is reported in a 6-yr-old child with extensive and progressive cerebral atrophy. The concentration in urine was 947-1,433 mumol/mmol creatinine (controls, n = 10, 5-21 mumol/mmol creatinine) and the daily excretion approximately 3-4
Studies on the metabolic pathway of the acetyl group for acetylcholine synthesis.
G E Gibson et al.
Biochemical pharmacology, 29(2), 167-174 (1980-02-01)

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