ChemicalBook > CAS DataBase List > Urocanic acid
Urocanic acid
- Product Name
- Urocanic acid
- 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
- Formula Weight
- 138.12
- MOL File
- 104-98-3.mol
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Urocanic acid Property
- 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)
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Safety
- Safety Statements
- 22-24/25
- WGK Germany
- 3
- RTECS
- NI3425200
- HazardClass
- IRRITANT
- HS Code
- 29332990
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N-Bromosuccinimide Price
Sigma-Aldrich
- Product number
- 859796
- Product name
- 4-Imidazoleacrylic acid
- Purity
- 99%
- Packaging
- 5g
- Price
- $54.3
- Updated
- 2024/03/01
Sigma-Aldrich
- Product number
- 859796
- Product name
- 4-Imidazoleacrylic acid
- Purity
- 99%
- Packaging
- 25g
- Price
- $258
- Updated
- 2024/03/01
Sigma-Aldrich
- Product number
- 859796
- Product name
- 4-Imidazoleacrylic acid
- Purity
- 99%
- Packaging
- 100g
- Price
- $813
- Updated
- 2024/03/01
TRC
- Product number
- U847063
- Product name
- UrocanicAcid
- Packaging
- 250mg
- Price
- $50
- Updated
- 2021/12/16
Biosynth Carbosynth
- Product number
- FU29984
- Product name
- Urocanic acid
- Packaging
- 5G
- Price
- $50
- Updated
- 2021/12/16
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Urocanic acid Chemical Properties,Usage,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
Hydrogen Sulfide
PICRIC ACID
Ammonium hydroxide
Piperidine
Manganese dioxide
Formaldehyde
D(-)-Fructose
Benzene
Hydrochloric acid
Copper(II) sulfate
Pyridine
Isopropyl alcohol
Malonic acid
Sodium carbonate
Preparation Products
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View Lastest Price from Urocanic acid manufacturers
Hebei Weibang Biotechnology Co., Ltd
- Product
- Urocanic acid 104-98-3
- Price
- US $0.00-0.00/KG
- Min. Order
- 50KG
- Purity
- 99%
- Supply Ability
- 500000kg
- Release date
- 2022-09-29
Hebei Mojin Biotechnology Co., Ltd
- Product
- Urocanic acid 104-98-3
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 50000KG/month
- Release date
- 2023-11-13
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