Isochorismate(2-)

Base Information

• Chemical Name: Isochorismate(2-)
• CAS No.: 22642-82-6
• Molecular Formula: C₁₀H₁₀O₆
• Molecular Weight: 226.186
• DSSTox Substance ID: DTXSID20945303
• Wikidata: Q27110272
• Mol file: 22642-82-6.mol

Synonyms:isochorismate(2-);CHEBI:29780;DTXSID20945303;DB02793;Q27110272;5-[(1-Carboxylatoethenyl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylate;(5S,6S)-5-[(1-carboxylatoethenyl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylate

Chemical Property of Isochorismate(2-)

Chemical Property:

• Vapor Pressure: 8.17E-15mmHg at 25°C
• Boiling Point: 558.8°Cat760mmHg
• Flash Point: 226.8°C
• PSA: 109.72000
• Density: 1.49g/cm³
• LogP: -2.75780
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 224.03208797
• Heavy Atom Count: 16
• Complexity: 381

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C(C(=O)[O-])OC1C=CC=C(C1O)C(=O)[O-]
• Isomeric SMILES: C=C(C(=O)[O-])O[C@H]1C=CC=C([C@@H]1O)C(=O)[O-]

Technology Process of Isochorismate(2-)

There total 10 articles about Isochorismate(2-) 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: 23.0%

dimethyl isochrismate (85442-95-1) → (5S,6S)-5-(1-Carboxy-vinyloxy)-6-hydroxy-cyclohexa-1,3-dienecarboxylic acid (22642-82-6,85506-20-3)

Guidance literature:

With sodium hydroxide; In methanol; at 0 ℃;

DOI:10.1021/ja00348a070

Reference yield: 9.0%

shikimic acid (138-59-0) + phospho(enol)pyruvic acid mono potassium salt (4265-07-0) → chorismic acid (617-12-9) + (+)-isochorismic acid (85506-20-3,22642-82-6)

Guidance literature:

With crude cell extract from E_.coli strain KA₁₂; pKAD₅₀; pKS₃-02; Flavin mononucleotide; ATP; sodium dithionite; In various solvent(s); at 23 ℃; for 1h;

DOI:10.1021/ja056714x

Reference yield:

chorismic acid (617-12-9) → (+)-isochorismic acid (85506-20-3,22642-82-6)

Guidance literature:

With Tris-Mg₂+; water; at 37 ℃; for 2h; Mechanism; isochorismate synthase; also with H₂¹⁸O;

DOI:10.1016/S0040-4020(01)86490-5

upstream raw materials:

chorismic acid

shikimic acid

phospho(enol)pyruvic acid mono potassium salt

chorismic acid

Downstream raw materials:

2-oxo-propionic acid

3-¹⁸O-3-hydroxybenzoic acid