Urocanic acid

Base Information

• Chemical Name: Urocanic acid
• CAS No.: 3465-72-3
• Deprecated CAS: 7699-36-7
• Molecular Formula: C6H6N2O2
• Molecular Weight: 138.126
• Hs Code.: 2933290090
• European Community (EC) Number: 203-258-4
• NSC Number: 407934,66357
• UNII: G8D26XJJ3B
• DSSTox Substance ID: DTXSID5041148
• Nikkaji Number: J168.822G,J5.039C,J2.069.797K
• Wikipedia: Urocanic_acid
• Wikidata: Q30536,Q60998685
• Metabolomics Workbench ID: 37193
• ChEMBL ID: CHEMBL1236602
• Mol file: 3465-72-3.mol

Synonyms:Acid, Glyoxalinylacrylic;Acid, Urocanic;Glyoxalinylacrylic Acid;Urocanic Acid

Chemical Property of Urocanic acid

Chemical Property:

• Melting Point: 225 °C
• Boiling Point: 456.9 °C at 760 mmHg
• Flash Point: 230.1 °C
• PSA: 65.98000
• Density: 1.43 g/cm³
• LogP: 0.50750
• Storage Temp.: 2-8°C
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 138.042927438
• Heavy Atom Count: 10
• Complexity: 156

Purity/Quality:

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

(E)-3-(1H-Imidazol-5-yl)acrylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(NC=N1)C=CC(=O)O
• Isomeric SMILES: C1=C(NC=N1)/C=C/C(=O)O

Technology Process of Urocanic acid

There total 17 articles about Urocanic 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:

2-(1H-imidazol-4-yl)acetic acid (645-65-8) + sodium thiosulfate + Chloroacetic anhydride (541-88-8) → urocanic Acid (3465-72-3)

Guidance literature:

With sodium iodide; sodium hydrogencarbonate; triethylamine; In N-methyl-acetamide; water; N,N-dimethyl-formamide;

Reference yield:

(1(3)H-imidazol-4-ylmethylene)-malonic acid (178764-94-8) → urocanic Acid (3465-72-3)

Guidance literature:

With acetic anhydride;

Reference yield:

L-histidine (71-00-1) → urocanic Acid (3465-72-3)

Guidance literature:

With Tris buffer; ammonium acetate; In water; at 25 ℃; for 144h; Equilibrium constant; Thermodynamic data; histidine ammonia-lyase, pH 8.70; var. temp.; Δ_rH'_m;

DOI:10.1006/jcht.1993.1009

upstream raw materials:

(1⁽³⁾H-imidazol-4-ylmethylene)-malonic acid

5-imidazolecarboxaldehyde

malonic acid

D,L-histidine

Downstream raw materials:

4⁽⁵⁾-vinyl imidazole

L-histidine

trans-4-imidazoleacrylic acid methyl ester hydrochloride

methyl (E)-3-(1H-imidazol-5-yl)prop-2-enoate

Refernces

• 1、 Reilly, John T.,Troester, Kyle A.,Tyner, Trista T.,Vitale, Dominick A.,Risher, Tiffiany R.. "Inhibition of histidine ammonia lyase by 8-methoxypsoralen and psoralen-oxidized photoproducts". . p. 1272 - 1277. Retrieved 2010.
• 2、 Gong, Pei-Xue,Xu, Fangning,Cheng, Lu,Gong, Xu,Zhang, Jie,Gu, Wei-Jin,Han, Wei. "Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation". supporting information. p. 5905 - 5908. Retrieved 2021/06/18.
• 3、 Valeev,Salikhov,Krasnoslobodtseva,Sharipov,Spirikhin,Tolstikov. "Synthesis of N-methyl urocanates of hydroxyderivatives of isocembrol". . p. 143 - 148. Retrieved 2008/03/11.