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SML1836

Sigma-Aldrich

β-ODAP

≥98% (HPLC)

Synonym(s):

β-N-Oxalo-L-α,β-diaminopropionic acid, β-N-Oxalyl-L-α,β-diaminopropionate, 3-[(Carboxycarbonyl)amino]-L-alanine, BOAA, Dencichin, Dencichine, Nβ-Oxalylamino-L-alanine, ODAP

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About This Item

Empirical Formula (Hill Notation):
C5H8N2O5
CAS Number:
5302-45-4
Molecular Weight:
176.13
MDL number:
MFCD00055228
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -17 to -23°, c = 0.5 (Solvent: 4N HCl)

color

white to beige

solubility

0.1 M HCl: 2 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

OC([C@@H](N)CNC(C(O)=O)=O)=O

InChI

1S/C5H8N2O5/c6-2(4(9)10)1-7-3(8)5(11)12/h2H,1,6H2,(H,7,8)(H,9,10)(H,11,12)/t2-/m0/s1

InChI key

NEEQFPMRODQIKX-REOHCLBHSA-N

Biochem/physiol Actions

β-ODAP is a potent inhibitor of HIF-prolyl hydroxylase-2 (PHD-2) that induces HIF dependent HRE (hypoxia response element) in normoxic conditions. β-ODAP is an analog of glutamic acid present in Lathyrus sativus (grass pea) that activates AMPA receptors. β-ODAP causes neurolathyrism upon prolonged consumption of L. sativus seeds.
β-ODAP is considered more neurotoxic than α-ODAP, thus during food processing, its conversion to α isomer is essential. β-ODAP exhibits its neurotoxicity via the activation of metabotropic glutamatergic receptor.

Storage Class

11 - Combustible Solids

wgk_germany

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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Kuniko Kusama-Eguchi et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 67, 113-122 (2014-03-04)
Neurolathyrism is a motor neuron (MN) disease caused by β-N-oxalyl-L-α,β-diaminopropionic acid (L-β-ODAP), an AMPA receptor agonist. L-β-ODAP caused a prolonged rise of intracellular Ca(2+) ([Ca(2+)]i) in rat spinal cord MNs, and the [Ca(2+)]i accumulation was inversely proportional to the MN's
Ravi Kumar Eslavath et al.
European journal of pharmacology, 791, 405-411 (2016-10-30)
Hypoxia inducible factor (HIF)-1α, a subunit of HIF transcription factor, regulates cellular response to hypoxia. In normoxic conditions, it is hydroxylated by prolyl hydroxylase (PHD)-2 and targeted for proteosomal degradation. Drugs which inhibit PHD-2 have implications in conditions arising from
Medical Toxicology of Natural Substances: Foods, Fungi, Medicinal Herbs, Plants, and Venomous Animals (2012)
Nalini Jammulamadaka et al.
Journal of neurochemistry, 118(2), 176-186 (2011-05-11)
β-N-Oxalyl-L-α,β-diaminopropionic acid (l-ODAP) an α-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid (AMPA) receptor agonist activates protein kinase C in white leghorn chick brain. The current study focuses on the protein kinase C downstream signaling targets associated with L-ODAP excitotoxicity in SK-N-MC human neuroblastoma cells

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