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Supelco

L-2-Aminoadipic acid

analytical standard

Synonym(s):

(S)-2-Aminohexanedioic acid, L-Homoglutamic acid, Aad

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About This Item

Linear Formula:
HO2C(CH2)3CH(NH2)CO2H
CAS Number:
1118-90-7
Molecular Weight:
161.16
Beilstein/REAXYS Number:
1724348
MDL number:
MFCD00002636
UNSPSC Code:
41116107

grade

analytical standard

assay

≥98% (TLC)

optical activity

[α]25/D 24±1°, c = 2 in 5 M HCl

shelf life

limited shelf life, expiry date on the label

mp

203-205 °C (dec.) (lit.)

application(s)

clinical testing

format

neat

SMILES string

N[C@@H](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)/t4-/m0/s1

Inchi Key

OYIFNHCXNCRBQI-BYPYZUCNSA-N

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General description

L-2-Aminoadipic acid is the six-carbon homolog of glutamate and a metabolite of L-lysine.

Application

L-2-Aminoadipic acid may be used as an analytical standard in the following:
  • For the quantification of 2-aminoadipic acid in acid hydrolysates of processed skin samples using gas chromatography coupled to mass spectrometry (GC-MS).
  • To investigate its effect on proteolysis and protein synthesis in C2C12 myotubes.

It may be used as an internal standard for the determination of free amino acids and ammonium ion contents in Crocus sativus L. from different geographical origins using high-performance liquid chromatography with diode array detection (HPLC-DAD).

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Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH5626
BCCF1020
BCBZ5987

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Determination of free amino acids and ammonium ion in saffron (Crocus sativus L.) from different geographical origins
Campo dPC, et al.
Food Chemistry, 114(4), 1542-1548 (2009)
Maho Shibata et al.
Investigative ophthalmology & visual science, 53(7), 3726-3732 (2012-05-17)
To investigate the involvement of glial cells in the autoregulation of optic nerve head (ONH) blood flow in response to elevated intraocular pressure (IOP). Rabbit eyes were treated with an intravitreal injection of l-2-aminoadipic acid (LAA), a gliotoxic compound. Twenty-four
David R Sell et al.
The Biochemical journal, 404(2), 269-277 (2007-02-23)
We hypothesized that the epsilon-amino group of lysine residues in longlived proteins oxidatively deaminates with age forming the carbonyl compound, allysine (alpha-aminoadipic acid-delta-semialdehyde), which can further oxidize into 2-aminoadipic acid. In the present study, we measured both products in insoluble
Regulatory effects of the L-lysine metabolites, L-2-aminoadipic acid and L-pipecolic acid, on protein turnover in C2C12 myotubes
Sato T, et al.
Bioscience, Biotechnology, and Biochemistry, 80(11), 2168-2175 (2016)

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