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Merck
CN

00920

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:
997-55-7
Molecular Weight:
175.14
NACRES:
NA.22
PubChem Substance ID:
329747163
eCl@ss:
32160406
UNSPSC Code:
12352209
MDL number:
MFCD00020500
Beilstein/REAXYS Number:
1726198
Assay:
≥99.0% (T)
Form:
powder

Key Documents

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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

SMILES string

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

InChI key

OTCCIMWXFLJLIA-BYPYZUCNSA-N

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

Quality Level

100

Related Categories

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG9464
BCCB2022
BCBR3519V

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Synthesis and anticonvulsant activity of racemic 2-amino-N-substituted succinimide derivatives
Criderx AM, et al.
Journal of Pharmaceutical Sciences, 70(2), 192-195 (1981)
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)
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
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
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