- Urocanic acid
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- $0.00 / 25KG
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2025-08-08
- CAS:104-98-3
- Min. Order: 1KG
- Purity: 99%
- Supply Ability: 50000KG/month
- Urocanic acid
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- $0.00 / 1KG
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2025-06-27
- CAS:104-98-3
- Min. Order: 50KG
- Purity: 99%
- Supply Ability: 500000kg
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| | Urocanic acid Basic information |
| | Urocanic acid Chemical Properties |
| 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. | Keep in dark place,Sealed in dry,2-8°C | | solubility | 1.5g/l | | pka | 2.94±0.10(Predicted) | | form | Powder | | 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 | 2-Propenoic acid, 3-(1H-imidazol-4-yl)- (104-98-3) |
| Safety Statements | 22-24/25 | | WGK Germany | 3 | | RTECS | NI3425200 | | HazardClass | IRRITANT | | HS Code | 29332990 |
| | Urocanic acid Usage And Synthesis |
| Chemical Properties | White to beige fine powder. | | Uses | Urocanic Acid is a biomarker in the fecal metabolic profiling of breast cancer patients. | | Definition | ChEBI:
Urocanic acid is 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. It has a role as a chromophore and a human metabolite. It is an alpha,beta-unsaturated monocarboxylic acid and a member of imidazoles. It is a conjugate acid of a urocanate. | | 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.] |
| | Urocanic acid Preparation Products And Raw materials |
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