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7699-35-6 molecular structure
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3-(1H-imidazol-4-yl)prop-2-enoic acid

ChemBase ID: 1738
Molecular Formular: C6H6N2O2
Molecular Mass: 138.12404
Monoisotopic Mass: 138.04292744
SMILES and InChIs

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

Cite this record

CBID:1738 http://www.chembase.cn/molecule-1738.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

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

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.8470757  H Acceptors
H Donor LogD (pH = 5.5) -1.0751153 
LogD (pH = 7.4) -2.2414906  Log P -1.0052562 
Molar Refractivity 35.5676 cm3 Polarizability 13.067313 Å3
Polar Surface Area 65.98 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.0  LOG S -0.82 
Solubility (Water) 2.10e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
1.5 mg/mL at 17 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] expand Show data source
H2O: >10 mg/mL expand Show data source
Apperance
white solid (fluffy) expand Show data source
Melting Point
>215°C(dec) expand Show data source
225°C expand Show data source
226-228 °C(lit.) expand Show data source
dec > 215 °C expand Show data source
Storage Condition
2-8°C expand Show data source
Light sensitive expand Show data source
protect from light expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
NI3425200 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
R:36/37/38 expand Show data source
Safety Statements
S:20-25-26-37/39 expand Show data source
TSCA Listed
false expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
2-8°C expand Show data source
Mechanism of Action
Gabaminergic expand Show data source
Purity
>95% expand Show data source
≥98% (HPLC) expand Show data source
≥99.0% (T) expand Show data source
99% expand Show data source
Grade
purum expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Application(s)
Shows antineoplastic activity expand Show data source
Sunscreen expand Show data source
Empirical Formula (Hill Notation)
C6H6N2O2 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
MP Biomedicals - 02103221 external link
Crystalline
MP Biomedicals - 05206291 external link
MP Biomedicals Rare Chemical collection
DrugBank - DB01971 external link
Drug information: experimental
Sigma Aldrich - U6883 external link
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 external link
Packaging
25, 100 g in poly bottle
5 g in glass bottle

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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