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A0637

Sigma-Aldrich

DL-2-Aminoadipic acid

≥99% (TLC), powder, gliotoxic

Synonym(s):

DL-α-Aminoadipic acid

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About This Item

Linear Formula:
HO2C(CH2)3CH(NH2)CO2H
CAS Number:
542-32-5
Molecular Weight:
161.16
EC Number:
208-809-2
MDL number:
MFCD00063119
UNSPSC Code:
12352106
PubChem Substance ID:
24890441
NACRES:
NA.32

product name

DL-2-Aminoadipic acid, ≥99%

Assay

≥99%

form

powder

mp

196-198 °C (lit.)

storage temp.

2-8°C

SMILES string

NC(CCCC(O)=O)C(O)=O

InChI

1S/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11)

InChI key

OYIFNHCXNCRBQI-UHFFFAOYSA-N

Gene Information

rat ... Grin2b(24410)

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Application

DL-2-Aminoadipic acid (AAA) has been used as an astrotoxin to kill astrocytes that prevent efficient integration of transplanted cells into the retina. It has also been used as a gliotoxin to study the effect of astrocytic swelling on the tortuosity.

Biochem/physiol Actions

DL-2-Aminoadipic acid (AAA) is a six-carbon homolog of glutamate and a gliotoxic compound. It is generally used to considerably reduce the number of astroglia in cerebellar cultures that acts as a model to study the mechanisms of a-aminoadipic acid induced glial toxicity.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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H Bräuner-Osborne et al.
Journal of medicinal chemistry, 39(16), 3188-3194 (1996-08-02)
The homologous series of acidic amino acids, ranging from aspartic acid (1) to 2-aminosuberic acid (5), and the corresponding series of 3-isoxazolol bioisosteres of these amino acids, ranging from (RS)-2-amino-2-(3-hydroxy-5-methylisoxazol-4-yl)acetic acid (AMAA, 6) to (RS)-2-amino-6-(3-hydroxy-5-methylisoxazol-4-yl)hexanoic acid (10), were tested as
Bhagyalaxmi S Ganesh et al.
PloS one, 6(3), e18305-e18305 (2011-04-13)
Reactive gliosis is a hallmark of many retinal neurodegenerative conditions, including glaucoma. Although a majority of studies to date have concentrated on reactive gliosis in the optic nerve head, very few studies have been initiated to investigate the role of
Saadet Mercimek-Mahmutoglu et al.
Pediatrics, 129(5), e1368-e1372 (2012-04-25)
Pyridoxine-dependent epilepsy (PDE) was first described in 1954. The ALDH7A1 gene mutations resulting in α-aminoadipic semialdehyde dehydrogenase deficiency as a cause of PDE was identified only in 2005. Neonatal epileptic encephalopathy is the presenting feature in >50% of patients with
H Q Wu et al.
European journal of pharmacology, 281(1), 55-61 (1995-07-25)
L-alpha-Aminoadipic acid is a lysine metabolite with neuroexcitatory properties, and has previously been shown to inhibit the production of the broad spectrum excitatory amino acid receptor antagonist kynurenic acid in brain tissue slices. The effects of L-alpha-aminoadipic acid on the
Gliotoxin-induced swelling of astrocytes hinders diffusion in brain extracellular space via formation of dead-space microdomains
Sherpa AD, et al.
Glia, 62(7), 1053-1065 (2014)
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