Chorismic acid

Base Information

• Chemical Name: Chorismic acid
• CAS No.: 617-12-9
• Molecular Formula: C10H10 O6
• Molecular Weight: 226.186
• European Community (EC) Number: 636-403-9,637-247-4
• UNII: GI1BLY82Y1
• DSSTox Substance ID: DTXSID50210697
• Nikkaji Number: J7.035A
• Wikipedia: Chorismic_acid
• Wikidata: Q423531
• Metabolomics Workbench ID: 41906
• Mol file: 617-12-9.mol

Synonyms:Acid, Chorismic;Chorismic Acid

Chemical Property of Chorismic acid

Chemical Property:

• Vapor Pressure: 1.11E-14mmHg at 25°C
• Melting Point: 105-108° (dec)
• Boiling Point: 556.1°C at 760 mmHg
• PKA: 3.59±0.11(Predicted)
• Flash Point: 225.7°C
• PSA: 104.06000
• Density: 1.49g/cm³
• LogP: -0.08840
• Storage Temp.: −70°C
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 226.04773803
• Heavy Atom Count: 16
• Complexity: 392

Purity/Quality:

98%,99%, ^*data from raw suppliers

Chorismic acid from Enterobacter aerogenes ≥80% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 45-20/21/22-36/37/38-63
• Safety Statements: 53-23-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=C(C(=O)O)OC1C=C(C=CC1O)C(=O)O
• Isomeric SMILES: C=C(C(=O)O)O[C@@H]1C=C(C=C[C@H]1O)C(=O)O
• Uses: Chorismic acid is a metabolite generally used in the study of chorismate-prephenate rearrangement and to synthesize chorismate derivatives.

Technology Process of Chorismic acid

There total 13 articles about Chorismic acid 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: 40.0%

sodium shikimate (104975-34-0) + phospho(enol)pyruvic acid mono potassium salt (4265-07-0) → chorismic acid (617-12-9)

Guidance literature:

With pKAD₅₀; adenosine 5'-triphosphate sodium salt; Flavin mononucleotide; sodium dithionite; magnesium sulfate; In sodium hydroxide; at 23 ℃; for 1h; pH=8.1;

DOI:10.1021/ja052929v

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:

methyl shikimate (40983-58-2) → chorismic acid (617-12-9)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH / tetrahydrofuran / 8 h / 23 °C

2: 40 percent / ATP monosodium salt; KA₁₂/pKAD₅₀; FMN / sodium dithionite; MgSO₄ / aq. NaOH / 1 h / 23 °C / pH 8.1

With sodium hydroxide; pKAD₅₀; adenosine 5'-triphosphate sodium salt; Flavin mononucleotide; sodium dithionite; magnesium sulfate; In tetrahydrofuran; sodium hydroxide;

DOI:10.1021/ja052929v

upstream raw materials:

5-enol-pyruvoylshikimate 3-phosphate (EPSP)

sodium shikimate

phospho(enol)pyruvic acid mono potassium salt

shikimic acid

Downstream raw materials:

2,3-dihydro-2,3-dihydroxybenzoic acid

isochorismic acid

(4R:5R)-5-<1-Carboxy-vinyloxy>-4-hydroxy-cyclohex-1-en-1-carbonsaeure; 3,6-Dihydro-chorismic acid

dimethyl chorismate