Skip to Content
Merck
All Photos(1)

Documents

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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 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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service