| Identification | More | [Name]
Urocanic acid | [CAS]
104-98-3 | [Synonyms]
3-(1H-IMIDAZOL-4-YL)ACRYLIC ACID
3-(4-IMIDAZOLY)ACRYLIC ACID
3,4-IMIDAZOLYLACRYLIC ACID
4-IMIDAZOLEACRYLIC ACID
B 4(5)-GLYOXALINYLACRYLIC ACID
(E)-3-(1H-IMIDAZOL-4-YL)-ACRYLIC ACID
IMIDAZOLE-4-ACRYLIC ACID
RARECHEM AL BK 0762
TIMTEC-BB SBB006702
UROCANIC ACID
UROCANINIC ACID
3-(1h-imidazol-4-yl)-2-propenoicaci
3-(1h-imidazol-4-yl)-2-propenoicacid
3-imidazol-4-ylacrylic
3-imidazol-4-ylacrylicacid
5-imidazoleacrylicacid
imidazoleacrylicacid
UROCANIC ACID 99%
Urocanic caid
2-Propenoic acid, 3-(1H-imidazol-4-yl)- | [EINECS(EC#)]
203-258-4 | [Molecular Formula]
C6H6N2O2 | [MDL Number]
MFCD00005203 | [Molecular Weight]
138.12 | [MOL File]
104-98-3.mol |
| Chemical Properties | Back Directory | [Appearance]
white to beige fine powder | [Melting point ]
226-228 °C(lit.)
| [Boiling point ]
253.51°C (rough estimate) | [density ]
1.3471 (rough estimate) | [refractive index ]
1.5100 (estimate) | [storage temp. ]
2-8°C
| [solubility ]
1.5g/l | [form ]
Powder | [pka]
2.94±0.10(Predicted) | [color ]
White to beige | [biological source]
synthetic | [Water Solubility ]
SLIGHTLY SOLUBLE | [BRN ]
81405 | [InChI]
InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10) | [InChIKey]
LOIYMIARKYCTBW-UHFFFAOYSA-N | [SMILES]
C(O)(=O)C=CC1NC=NC=1 | [CAS DataBase Reference]
104-98-3(CAS DataBase Reference) | [EPA Substance Registry System]
104-98-3(EPA Substance) |
| Safety Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [RTECS ]
NI3425200
| [HazardClass ]
IRRITANT | [HS Code ]
29332990 |
| Hazard Information | Back Directory | [Chemical Properties]
white to beige fine powder | [Uses]
Urocanic Acid is a biomarker in the fecal metabolic profiling of breast cancer patients. | [Definition]
ChEBI: An alpha,beta-unsaturated monocarboxylic acid that is prop-2-enoic acid substituted by a 1H-imidazol-4-yl group at position 3. It is a metabolite of hidtidine. | [Biological Functions]
Urocanic acid, produced in the upper layers of mammalian skin, is a major absorber of ultraviolet radiation (UVR). Urocanic acid (UCA) is formed in the upper layers of the epidermis where filaggrin, a histidine-rich filamentous protein produced after caspase-14 cleavage of profilaggrin, is broken down by proteinases into component amino acids. | [General Description]
4-Imidazoleacrylic acid also known as urocanic acid is a natural metabolite derived from histidine. It is majorly used as a UV chromophore with a strong absorption spectrum in the UV-B region in the range of 300-280 nm. | [Synthesis]
A method of producing trans-urocanic acid, which involves treating D-glucose with aqueous ammonia and formalin in molar ratio D-glucose: aqueous ammonia: formalin equal to 1:24:2.7, in water in the presence of basic copper carbonate at temperature 85-90°C for 3 hours to form (1S,2S,3S)-1-(1H-imidazol-4-yl)-butane-1,2,3,4-tetrazole, which is extracted in form of a hydrochloride. Through periodate splitting in water, the obtained (1S,2S,3S)-1-(1H-imidazol-4-yl)-butane-1,2,3,4-tetrazole is converted at room temperature to 1H-imidazole-4-carbaldehyde, condensation of which, in acetic anhydride in the presence of anhydrous potassium acetate at temperature 120°C for 2 hours, leads to formation of trans-urocanic acid with subsequent extraction thereof from the reaction mass. | [Purification Methods]
Crystallise the acid from water and dry it at 100o. The trans-isomer [3465-72-3] has m 225o (229-230o, 230-231o or 231o(dec, from H2O) and pK1 3.5 and pK2 5.6, and the picrate has m 225o(dec, from H2O). The cis-isomer [7699-35-6] has m 175-176o (178-179o or 180-184o dec, from H2O) and pK1 3.0 and pK2 6.7, and the picrate has m 204o (from H2O). [Beilstein 25 H 124, 25 I 536, 25 II 121, 25 III/IV 786.] |
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