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UROCANIC ACID

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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 Molecular Structure of 104-98-3 (Urocanic acid) 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

UROCANIC ACID Synthetic route

71-00-1

L-histidine

104-98-3

urocanic acid

Conditions
ConditionsYield
With histidase EC 4.3.1.3; Tris buffer In water at 37℃; for 24h; pH=9.0;
With histidase Enzymatic reaction;
104-98-3

urocanic acid

49549-75-9

4-(3-hydroxypropyl)-1H-imidazole

Conditions
ConditionsYield
With lithium aluminium tetrahydride100%
67-56-1

methanol

104-98-3

urocanic acid

160073-02-9, 52363-40-3

methyl 3-(imidazol-4(5)-yl)-2-propenoate

Conditions
ConditionsYield
With thionyl chloride98%
With hydrogenchloride Reflux;94%
With sulfuric acid; magnesium sulfate Fischer esterification; Reflux;93%
67-56-1

methanol

104-98-3

urocanic acid

53958-94-4

3-(1H-imidazol-4-yl)propionic acid methyl ester hydrochloride

Conditions
ConditionsYield
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%
104-98-3

urocanic acid

3718-04-5

4(5)-vinyl imidazole

Conditions
ConditionsYield
at 250℃;93%
at 110℃;71%
at 240℃; under 0.0165017 Torr; for 6h;66%
67-56-1

methanol

104-98-3

urocanic acid

52838-22-9

methyl 3-[1H-imidazol-4-yl]propenoate hydrochloride salt

Conditions
ConditionsYield
With hydrogenchloride at 0℃; for 2h;87%
57260-73-8

N-BOC-1,2-diaminoethane

104-98-3

urocanic acid

4-((N-(N-tert-butoxycarbonyl-2-aminoethyl)-3-amino-3-oxo)prop-1-enyl)-1H-imidazole

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃;86%
64-17-5

ethanol

104-98-3

urocanic acid

52237-38-4

ethyl 3-(imidazol-4'-yl)-propanoate

Conditions
ConditionsYield
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%
67-56-1

methanol

104-98-3

urocanic acid

70346-51-9

(E)-methyl 3-(1H-imidazol-4-yl)acrylate

Conditions
ConditionsYield
Stage #1: methanol; urocanic acid With thionyl chloride for 16h; Reflux;
Stage #2: With sodium carbonate In water; ethyl acetate
81%
70-34-8

2,4-Dinitrofluorobenzene

104-98-3

urocanic acid

507444-19-1

3-[1-(2,4-dinitrophenyl)-1H-imidazol-4-yl]propenoic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In methanol; water at 20℃; for 16h; Substitution;76%

UROCANIC ACID Chemical Properties

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).

 

UROCANIC ACID History

Urocanic acid was first isolated in 1874 by the chemist M. Jaffé from the urine of a dog.

UROCANIC ACID Toxicity Data With Reference

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.

UROCANIC ACID Consensus Reports

Reported in EPA TSCA Inventory.

UROCANIC ACID Safety Profile

Poison by intravenous route. Mutation data reported. When heated to decomposition it emits toxic vapors of NOx.
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