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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:
997-55-7
Molecular Weight:
175.14
Beilstein/REAXYS Number:
1726198
MDL number:
MFCD00020500
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
329747163
NACRES:
NA.22

Quality Level

100

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

11 - Combustible Solids

wgk_germany

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
BCBL3992V
BCBG2051V

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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
A Microwave-Assisted Synthesis of (S)-N-Protected Homoserine γ-Lactones from l-Aspartic Acid
Singh SP, et al.
The Journal of Organic Chemistry, 76(16), 6825-6831 (2011)
R. Bakhash et al.
Bios (Madison, N.J.), 49, 13-13 (1978)
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
Paola Leone et al.
Science translational medicine, 4(165), 165ra163-165ra163 (2012-12-21)
Canavan disease is a hereditary leukodystrophy caused by mutations in the aspartoacylase gene (ASPA), leading to loss of enzyme activity and increased concentrations of the substrate N-acetyl-aspartate (NAA) in the brain. Accumulation of NAA results in spongiform degeneration of white
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