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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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25 ML
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Estimated to ship onMarch 21, 2025


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25 ML
$391.00

About This Item

Linear Formula:
HO2C(CH2)3CH(NH2)CO2H
CAS Number:
Molecular Weight:
161.16
EC Number:
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.32

$391.00


Estimated to ship onMarch 21, 2025


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Product Name

DL-2-Aminoadipic acid, ≥99%

Quality Level

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

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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.[1]

Biochem/physiol Actions

DL-2-Aminoadipic acid (AAA) is a six-carbon homolog of glutamate[2] and a gliotoxic compound.[3] 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.[2]

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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    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)
    Gliotoxic effects of $\alpha$-aminoadipic acid on monolayer cultures of dissociated postnatal mouse cerebellum
    Huck S, et al.
    Neuroscience, 12(3), 783-791 (1984)
    Huadong Ni et al.
    Journal of neuroinflammation, 16(1), 1-1 (2019-01-05)
    Despite accumulating evidence on the role of glial cells and their associated chemicals in mechanisms of pain, few studies have addressed the potential role of chemokines in the descending facilitation of chronic pain. We aimed to study the hypothesis that
    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

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