cis-Urocanic acid

Base Information

• Chemical Name: cis-Urocanic acid
• CAS No.: 7699-35-6
• Molecular Formula: C6H6N2O2
• Molecular Weight: 138.126
• Hs Code.: 2933290090
• UNII: 5LM7WD7VIC
• DSSTox Substance ID: DTXSID901316398
• Nikkaji Number: J168.823E
• Wikidata: Q27113993
• NCI Thesaurus Code: C99125
• Pharos Ligand ID: A4TDUTJCUKNN
• Metabolomics Workbench ID: 46400
• ChEMBL ID: CHEMBL1316726
• Mol file: 7699-35-6.mol

Synonyms:cis-Urocanic acid;7699-35-6;cis-UCA;Imidazole-4-acrylic acid, (Z)-;(Z)-Imidazole-4-acrylic acid;Urocanic acid, cis-;(Z)-3-(1H-imidazol-5-yl)prop-2-enoic acid;UNII-5LM7WD7VIC;(E)-Urocanic acid;5LM7WD7VIC;CHEBI:30818;NSC 407934;NSC-407934;(Z)-3-(1H-Imidazol-5-yl)acrylic acid;(Z)-3-(3H-imidazol-4-yl)prop-2-enoic Acid;(2Z)-3-(1H-imidazol-4-yl)prop-2-enoic acid;(Z)-Urocanic acid;MFCD11045310;Lopac-U-7500;cis-3-(1H-imidazol-4-yl)-2-propenoic acid;SCHEMBL1755678;CHEMBL1316726;SCHEMBL12963908;DTXSID901316398;HY-113008A;NCGC00016079-01;MS-22807;CS-0109435;(2Z)-3-(1H-imidazol-5-yl)prop-2-enoic acid;cis-Urocanic acid, >=98% (HPLC), solid (fluffy);(E)-3-(3H-IMIDAZOL-4-YL)PROP-2-ENOIC ACID;Q27113993;2-PROPENOIC ACID, 3-(1H-IMIDAZOL-5-YL)-, (2Z)-

Chemical Property of cis-Urocanic acid

Chemical Property:

• PSA: 65.98000
• LogP: 0.50750
• Storage Temp.: −20°C
• Sensitive.: Light Sensitive
• Solubility.: H2O: >10mg/mL
• Water Solubility.: Soluble in water
• 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

cis-Urocanic acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(NC=N1)C=CC(=O)O
• Isomeric SMILES: C1=C(NC=N1)/C=C\C(=O)O
• Recent ClinicalTrials: Cis-urocanic Acid (Cis-UCA) in Patients With Primary or Recurrent Non-muscle Invasive Bladder Cancer
• Recent EU Clinical Trials: Double-blind, placebo-controlled, multi-centre Phase II study to investigate dose response, safety, tolerability and efficacy of topical twice daily doses of 2.5% and 5% cis-urocanic acid in comparison to active comparator 0.1% Protopic? for up to 28 days in patients with moderate or severe atopic dermatitis
• Uses: cis-Urocanic acid is an agonist of the 5-HT2A receptor.

Technology Process of cis-Urocanic acid

There total 8 articles about cis-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: 94.0%

Methyl-cis-urocanate (88181-49-1) → (Z)-urocanic acid (7699-35-6)

Guidance literature:

With sodium hydroxide; for 3h;

DOI:10.1080/00304940009355956

Reference yield: 78.0%

methyl (E)-3-(1H-imidazol-5-yl)prop-2-enoate (70346-51-9) → [3H]-cis-Urocanic acid (7699-35-6)

Guidance literature:

methyl (E)-3-(1H-imidazol-5-yl)prop-2-enoate; at 850 ℃; for 0.333333h; under 0.01 - 0.06 Torr; Flash photolysis;

In tetrahydrofuran; water; for 0.75h; Further stages.; Heating;

DOI:10.1055/s-2008-1067044

Reference yield: 58.0%

urocanic Acid (3465-72-3) → (Z)-urocanic acid (7699-35-6)

Guidance literature:

With potassium hydroxide; In water; at 10 ℃; for 4h; pH=9.0; UV-irradiation;

upstream raw materials:

urocanic Acid

Methyl-cis-urocanate

(E)-3-(1H-imidazol-4-yl)propenoic acid

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

Downstream raw materials:

urocanic Acid

Refernces

• 1、 Mohammad, Taj. "Laser-induced in vitro isomerization of urocanic acid in UVA region and the origin of excited triplet state". . p. 8897 - 8900. Retrieved 2002.
• 2、 Ryan,Levy. "Electronic spectroscopy and photoisomerization of trans-Urocanic acid in a supersonic jet". . p. 961 - 966. Retrieved 2001.
• 3、 Wallis, Richard A.,Smith, Gerald J.,Dunford, Cara L.. "The effect of molecular environment on the photoisomerization of urocanic acid". . p. 257 - 261. Retrieved 2004.
• 4、 Menon, Elton L,Morrison, Harry. "Formation of singlet oxygen by urocanic acid by UVA irradiation and some consequences thereof.". . p. 565 - 569. Retrieved 2002.
• 5、 Despinoy, Xavier L. M.,McNab, Hamish,Tyas, Richard G.. "A stereospecific route to (Z)-Urocanic acids". . p. 1676 - 1678. Retrieved 2008/12/22.
• 6、 -. "PHARMACEUTICAL AND COSMETIC COMPOSITIONS COMPRISING UROCANIC ACID DERIVATIVES AS RADICAL SCAVENGERS OR ANTIOXIDANTS". Page/Page column 4; 5; 7; 8; 21; 22. . Retrieved 2008/06/13.