3-(1H-imidazol-4-yl)prop-2-enoic acid

• ChemBase ID: 1738
• Molecular Formular: C6H6N2O2
• Molecular Mass: 138.12404
• Monoisotopic Mass: 138.04292744
• SMILES: OC(=O)/C=C/c1c[nH]cn1
• Canonical SMILES: OC(=O)/C=C/c1c[nH]cn1
• InChI: InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1+
• InChIKey: LOIYMIARKYCTBW-OWOJBTEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(1H-imidazol-4-yl)prop-2-enoic acid; (2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid; (2E)-3-(1H-imidazol-5-yl)prop-2-enoic acid; 3-(1H-imidazol-5-yl)prop-2-enoic acid
• IUPAC Traditional name: urocanic acid; (2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid; trans-urocanic acid; (2E)-3-(3H-imidazol-4-yl)prop-2-enoic acid
• Synonyms: 4-Imidazoleacrylic acid; 4-Imidazoleacrylic acid; 3-(4-Imidazolyl)acrylic acid; UROCANIC ACID; (E)-3-(1H-imidazol-4-yl)acrylic acid; cis-3-(1H-imidazol-4-yl)-2-propenoic acid; cis-UCA; cis-Urocanic acid; 3-(1H-imidazol-4-yl)acrylic acid; 3-(1 H -Imidazol-4-yl)-2-propenoic acid; 4-Imidazoleacrylic acid; Urocaninic acid; Urocanic acid; (2e)-3-(1h-Imidazol-4-Yl)Acrylic Acid; (E)-3-(1H-Imidazol-5-yl)-2-propenoic acid; Urocanic acid; 3-(4-咪唑基)丙烯酸; 尿刊酸; 4-咪唑丙烯酸

Database IDs

• CAS Number: 104-98-3; 7699-35-6
• EC Number: 203-258-4
• MDL Number: MFCD01593677; MFCD00005203; MFCD11045310
• Beilstein Number: 81405
• PubChem SID: 160965194; 24888491
• PubChem CID: 1178; 736715
• MeSH Name: Urocanic+acid
• Wikipedia Title: Urocanic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.8470757
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.0751153
• LogD (pH = 7.4): -2.2414906
• Log P: -1.0052562
• Molar Refractivity: 35.5676 cm^3
• Polarizability: 13.067313 Å^3
• Polar Surface Area: 65.98 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.0
• LOG S: -0.82
• Solubility (Water): 2.10e+01 g/l

PROPERTIES

Physical Property

• Solubility: 1.5 mg/mL at 17 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; H2O: >10 mg/mL
• Apperance: white solid (fluffy)
• Melting Point: >215°C(dec); 225°C; 226-228 °C(lit.); dec > 215 °C

Safety Information

• Storage Condition: 2-8°C; Light sensitive; protect from light
• Storage Warning: IRRITANT
• RTECS: NI3425200
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: R:36/37/38
• Safety Statements: S:20-25-26-37/39
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Mechanism of Action: Gabaminergic

Product Information

• Purity: >95%; ≥98% (HPLC); ≥99.0% (T); 99%
• Grade: purum
• Application(s): Shows antineoplastic activity; Sunscreen
• Empirical Formula (Hill Notation): C6H6N2O2

DETAILS

MP Biomedicals - 02103221

Crystalline

MP Biomedicals - 05206291

MP Biomedicals Rare Chemical collection

DrugBank - DB01971

Drug information: experimental

Sigma Aldrich - U6883

Biochem/physiol Actions
cis-Urocanic acid, a 5-HT agonist, is a product of uv isomerization of trans-urocanic acid in skin, which leads to immunosuppression via activation of 5-HT2A receptor.

Sigma Aldrich - 859796

Packaging
25, 100 g in poly bottle
5 g in glass bottle

REFERENCES

• Aldrich Library of NMR Spectra, 2nd edn., 1983, 2, 492A, (nmr)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 621A, (ir)
• Edlbacher, S. et al., Hoppe Seyler's Z. Physiol. Chem., 1942, 276, 126; 1943, 279, 63, (isol, biosynth)
• Biochem. Prep., 1955, 4, 50, (synth)
• Gregoire, J. et al., Bull. Soc. Chim. Belg., 1958, 40, 767, (isol)
• List, F.H. et al., Hoppe Seyler's Z. Physiol. Chem., 1960, 319, 17, (isol)
• Japan. Pat., 1961, 61 23 094; CA, 60, 2302, (isol)
• Baden, H. et al., Nature (London), 1966, 210, 732, (pmr)
• Shibatari, T. et al., Appl. Microbiol., 1974, 27, 688, (biosynth)
• Svinning, T., Acta Cryst. B, 1979, 35, 2813, (cryst struct)
• Ienaga, K. et al., J. Het. Chem., 1988, 25, 1037, (deriv)
• Hanson, K.M. et al., J.A.C.S., 1997, 119, 2715, (spectra)