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Name |
UROCANIC ACID |
EINECS | 203-258-4 |
CAS No. | 104-98-3 | Density | 1.43 g/cm3 |
PSA | 65.98000 | LogP | 0.50750 |
Solubility | SLIGHTLY SOLUBLE | Melting Point |
226-228 °C(lit.) |
Formula | C6H6N2O2 | Boiling Point | 456.9 °C at 760 mmHg |
Molecular Weight | 138.126 | Flash Point | 230.1 °C |
Transport Information | N/A | Appearance | white to beige fine powder |
Safety | 22-24/25 | Risk Codes | N/A |
Molecular Structure | Hazard Symbols | N/A | |
Synonyms |
4-Imidazolylacrylic acid;5-Imidazoleacrylicacid;NSC 66357;Urocaninic acid;3-(1H-Imidazol-4-yl)acrylic acid;3-(4-Imidazolyl)acrylic acid;3-(1H-Imidazol-4-yl)-2-propenoic acid;Imidazole-4-acrylic acid (8CI);2-Propenoicacid, 3-(1H-imidazol-4-yl)- (9CI); |
Article Data | 8 |
Conditions | Yield |
---|---|
With histidase EC 4.3.1.3; Tris buffer In water at 37℃; for 24h; pH=9.0; | |
With histidase Enzymatic reaction; |
urocanic acid
4-(3-hydroxypropyl)-1H-imidazole
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride | 100% |
Conditions | Yield |
---|---|
With thionyl chloride | 98% |
With hydrogenchloride Reflux; | 94% |
With sulfuric acid; magnesium sulfate Fischer esterification; Reflux; | 93% |
methanol
urocanic acid
3-(1H-imidazol-4-yl)propionic acid methyl ester hydrochloride
Conditions | Yield |
---|---|
Stage #1: urocanic acid With hydrogenchloride; palladium 10% on activated carbon; hydrogen In methanol; water at 45℃; under 760.051 Torr; for 96h; Large scale; Stage #2: methanol With hydrogenchloride at 45℃; Large scale; | 98% |
Conditions | Yield |
---|---|
at 250℃; | 93% |
at 110℃; | 71% |
at 240℃; under 0.0165017 Torr; for 6h; | 66% |
methanol
urocanic acid
methyl 3-[1H-imidazol-4-yl]propenoate hydrochloride salt
Conditions | Yield |
---|---|
With hydrogenchloride at 0℃; for 2h; | 87% |
N-BOC-1,2-diaminoethane
urocanic acid
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; | 86% |
Conditions | Yield |
---|---|
Stage #1: urocanic acid With palladium on activated charcoal; hydrogen In methanol at 25℃; Stage #2: ethanol With sulfuric acid In methanol Reflux; Inert atmosphere; | 82% |
Stage #1: urocanic acid With palladium on activated charcoal; hydrogen In methanol at 25℃; Stage #2: ethanol With sulfuric acid Reflux; Inert atmosphere; | 82% |
Conditions | Yield |
---|---|
Stage #1: methanol; urocanic acid With thionyl chloride for 16h; Reflux; Stage #2: With sodium carbonate In water; ethyl acetate | 81% |
2,4-Dinitrofluorobenzene
urocanic acid
3-[1-(2,4-dinitrophenyl)-1H-imidazol-4-yl]propenoic acid
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In methanol; water at 20℃; for 16h; Substitution; | 76% |
Chemical Name: Urocanic acid
Molecular Formula: C6H6N2O2
molecular structure:
Formula Weight: 138.12
CAS No.: 104-98-3
CBNumber: CB8750635
Synonyms: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;3-(1H-IMIDAZOL-4-YL)ACRYLIC ACID;3-(4-IMIDAZOLY)ACRYLIC ACID
storage temp:2-8°C
mp :226-228 °C
slightly soluble in water
Urocanic acid is an intermediate in the catabolism of L-histidine.
Urocanic acid was detected in animal sweat and skin where, among other possible functions, it acts as an endogenous sunscreen or photoprotectant against UVB-induced DNA damage. When exposed to UVB irradiation, trans-urocanic acid is converted in vitro and in vivo to the cis isomer. The cis form is known to activate suppressor T cellsUrocanic acid is found predominantly in the stratum corneum of the skin and it is likely that most of it is derived from filaggrin catabolism (a histidine-rich protein).
1. | dni-hmn:oth 1 mmol/L | JIDEAE Journal of Investigative Dermatology. 65 (1975),400. | ||
2. | ivn-mus LD50:100 mg/kg | 85GDA2 CRC Handbook of Antibiotic Compounds. 5 (1981),81. |