Ibotenic acid, (S)-

Base Information

• Chemical Name: Ibotenic acid, (S)-
• CAS No.: 2552-55-8
• Molecular Formula: C5H6N2O4
• Molecular Weight: 158.114
• European Community (EC) Number: 622-405-7
• UNII: L61L2F576C
• Nikkaji Number: J386.590H
• Wikidata: Q27282755
• ChEMBL ID: CHEMBL30285
• Mol file: 2552-55-8.mol

Synonyms:L-Ibotenic acid;25690-45-3;Ibotenic acid, L-;Ibotenic acid, (S)-;CHEMBL30285;UNII-L61L2F576C;L61L2F576C;(2S)-2-amino-2-(3-oxo-1,2-oxazol-5-yl)acetic acid;(S)-2-amino-2-(3-oxo-2,3-dihydroisoxazol-5-yl)acetic acid;5-Isoxazoleacetic acid, alpha-amino-2,3-dihydro-3-oxo-, (alphaS)-;4-Isoxazoline-5-acetic acid, alpha-amino-3-oxo-, L-;(2S)-2-azaniumyl-2-(3-oxo-1,2-oxazol-5-yl)acetate;Ibotensaure;(RS)-Ibotenic acid;DL-Ibotenic acid;(S)-ibotenic acid;Tocris-0285;starbld0027536;Lopac-I-2765;SCHEMBL153360;SCHEMBL15732748;BDBM50034501;AKOS006311112;NCGC00015555-01;NCGC00015555-02;NCGC00024524-01;(S)-Amino-(3-hydroxy-isoxazol-5-yl)-acetic acid;Q27282755;(S)-Amino-(3-oxo-2,3-dihydro-isoxazol-5-yl)-acetic acid;4-ISOXAZOLINE-5-ACETIC ACID, .ALPHA.-AMINO-3-OXO-, L-;5-ISOXAZOLEACETIC ACID, .ALPHA.-AMINO-2,3-DIHYDRO-3-OXO-, (.ALPHA.S)-

Chemical Property of Ibotenic acid, (S)-

Chemical Property:

• Appearance/Colour: White powder
• Melting Point: 141-147 °C
• Refractive Index: 1.588
• PKA: 2.16±0.10(Predicted)
• PSA: 109.58000
• Density: 1.622 g/cm³
• LogP: 0.16490
• Storage Temp.: -20°C
• Solubility.: H2O: soluble1mg/mL, clear, colorless (with sonication)
• XLogP3: -3.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 158.03275668
• Heavy Atom Count: 11
• Complexity: 235

Purity/Quality:

99.9% ^*data from raw suppliers

Ibotenic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xn
• Hazard Codes: T,Xn
• Statements: 23/24/25-25-40
• Safety Statements: 45-38-36/37/39-28A-22-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(ONC1=O)C(C(=O)O)N
• Isomeric SMILES: C1=C(ONC1=O)[C@@H](C(=O)O)N
• Description: Ibotenic acid (60573-88-8) is a conformationally restricted analog of glutamate which occurs naturally in Amanita mascaria and related mushrooms.? It is a non-specific glutamate receptor (both NMDA and mGluR) agonist.1 May be used to induce hippocampal lesioning in rat neurodegeneration models.2,3 Induces lesions in the subiculum in a mouse model of Alzheimer’s disease.4
• Uses: Ibotenic acid has been used to perform surgery in adult male zebra finches (Taeniopygia guttata) to study reversing reinforcement-induced vocal changes. Ibotenic acid is a neuroexcitatory amino acid originally isolated from Amanita species that functions as a NMDA and metabotropic glutamate receptor agonist. As a neurotoxin, ibotenic acid is often used to induce brain lesions in animals that model cognitive dysfunctions resulting from neurodegenerative diseases, traumatic brain injury, and stroke. Neurobiological tool.

Technology Process of Ibotenic acid, (S)-

There total 4 articles about Ibotenic acid, (S)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ ibotenic acid (2552-55-8,25690-46-4)

Guidance literature:

α-Bromverb.,NH4OH;

Reference yield:

(3-benzyloxy-isoxazol-5-yl)-(toluene-4-sulfonyloxy)-acetic acid ethyl ester (2552-50-3) → ibotenic acid (2552-55-8)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBr / dimethylsulfoxide

2: (i) aq. HBr, AcOH, (ii) aq. NH₃

With sodium bromide; In dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)90158-8

Reference yield:

(3-benzyloxy-isoxazol-5-yl)-bromo-acetic acid ethyl ester (2552-49-0) → ibotenic acid (2552-55-8)

Guidance literature:

Multistep reaction; (i) aq. HBr, AcOH, (ii) aq. NH₃;

DOI:10.1016/S0040-4039(00)90158-8

upstream raw materials:

(3-benzyloxy-isoxazol-5-yl)-bromo-acetic acid ethyl ester

(3-benzyloxy-isoxazol-5-yl)-(toluene-4-sulfonyloxy)-acetic acid ethyl ester

Downstream raw materials:

amino-(2-oxo-2,3-dihydro-oxazol-5-yl)-acetic acid

Refernces

• 1、 Sirakawa,Aki,Tsushima,Konishi. "Synthesis of ibotenic acid and 3-deoxyibotenic acid.". . p. 89 - 91. Retrieved 1966.