Urocanic acid
![Urocanic acid Structure](CAS/GIF/104-98-3.gif)
- CAS No.
- 104-98-3
- Chemical Name:
- Urocanic acid
- Synonyms
- 4-IMIDAZOLEACRYLIC ACID;(E)-3-(1H-imidazol-5-yl)acrylic acid;3-(1H-IMIDAZOL-4-YL)ACRYLIC ACID;SKL080;UROCANIC ACID;Urocanic caid;Urocalic acid;urocanoic acid;UROCANINIC ACID;Urocanic acid,99%
- CBNumber:
- CB8750635
- Molecular Formula:
- C6H6N2O2
- Molecular Weight:
- 138.12
- MOL File:
- 104-98-3.mol
- MSDS File:
- SDS
- Modify Date:
- 2023/11/13 19:05:53
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 |
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
Risk and Safety Statements
Safety Statements | 22-24/25 |
---|---|
WGK Germany | 3 |
RTECS | NI3425200 |
HazardClass | IRRITANT |
HS Code | 29332990 |
Urocanic acid price More Price(3)
Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
---|---|---|---|---|---|---|---|
Sigma-Aldrich(India) | 859796 | 4-Imidazoleacrylic acid 99% | 104-98-3 | 5G | ₹4719.7 | 2022-06-14 | Buy |
Sigma-Aldrich(India) | 859796 | 4-Imidazoleacrylic acid 99% | 104-98-3 | 25G | ₹14646.23 | 2022-06-14 | Buy |
Sigma-Aldrich(India) | 859796 | 4-Imidazoleacrylic acid 99% | 104-98-3 | 100G | ₹46298.53 | 2022-06-14 | Buy |
Urocanic acid Chemical Properties,Uses,Production
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
Raw materials
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Supplier | Tel | Country | ProdList | Advantage | Inquiry |
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A.J Chemicals | 91-9810153283 | New Delhi, India | 6124 | 58 | Inquiry |
Alfa Aesar | 1 800 209 7001 | Maharashtra, India | 6913 | 58 | Inquiry |
Unipharm pharmaceutical industry Co., Ltd | 536-8266195 +8613953676784 | China | 1206 | 58 | Inquiry |
Hebei Mojin Biotechnology Co., Ltd | +8613288715578 | China | 12458 | 58 | Inquiry |
Capot Chemical Co.,Ltd. | 571-85586718 +8613336195806 | China | 29798 | 60 | Inquiry |
Shanghai Time Chemicals CO., Ltd. | +86-021-57951555 +8617317452075 | China | 1807 | 55 | Inquiry |
SHANDONG ZHI SHANG CHEMICAL CO.LTD | +86 18953170293 | China | 2931 | 58 | Inquiry |
Chongqing Chemdad Co., Ltd | +86-023-6139-8061 +86-86-13650506873 | China | 39916 | 58 | Inquiry |
CONIER CHEM AND PHARMA LIMITED | +8618523575427 | China | 49391 | 58 | Inquiry |
Career Henan Chemica Co | +86-0371-86658258 +8613203830695 | China | 30253 | 58 | Inquiry |
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