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Urocanic acid

CAS No.104-98-3
Chemical Name:Urocanic acid
CBNumber:CB8750635
Molecular Formula:C6H6N2O2
Formula Weight:138.12
MOL File:104-98-3.mol

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
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)
EWG's Food Scores 1-3
FDA UNII G8D26XJJ3B
EPA Substance Registry System 2-Propenoic acid, 3-(1H-imidazol-4-yl)- (104-98-3)
UNSPSC Code 12352005
NACRES NA.22

Safety

Safety Statements :22-24/25
WGK Germany :3
RTECS :NI3425200
HazardClass :IRRITANT
HS Code :29332990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Hazard statements
Precautionary statements

Urocanic acid Price More Price(3)

Brand: Sigma-Aldrich(India)
Product number: 859796
Product name : 4-Imidazoleacrylic acid
Purity: 99%
Packaging: 5G
Price: ₹4719.7
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 859796
Product name : 4-Imidazoleacrylic acid
Purity: 99%
Packaging: 25G
Price: ₹14646.23
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 859796
Product name : 4-Imidazoleacrylic acid
Purity: 99%
Packaging: 100G
Price: ₹46298.53
Updated: 2022/06/14
Buy: Buy

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.]