SML1836

β-ODAP

≥98% (HPLC), HIF-prolyl hydroxylase-2 (PHD-2) inhibitor, powder

• 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
• Empirical Formula (Hill Notation): C₅H₈N₂O₅
• CAS Number: 5302-45-4
• Molecular Weight: 176.13
• NACRES: NA.77
• UNSPSC Code: 12352200
• MDL number: MFCD00055228
• Assay: ≥98% (HPLC)
• Form: powder

Properties

• Product Name: β-ODAP, ≥98% (HPLC)
• Quality Segment: 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

Description

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 a potent inhibitor of HIF-prolyl hydroxylase-2 (PHD-2).

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable