UROCANIC ACID supplier | CasNO.104-98-3

Name
Urocanic acid
EINECS 203-258-4
CAS No. 104-98-3
Article Data8
CAS DataBase
Density 1.43 g/cm³
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
Appearance white to beige fine powder
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
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);
PSA 65.98000
LogP 0.50750

Synthetic route

: 71-00-1
L-histidine

: 104-98-3
urocanic acid

Conditions

Conditions	Yield
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

Conditions	Yield
With lithium aluminium tetrahydride	100%

: 67-56-1
methanol

: 104-98-3
urocanic acid

: 160073-02-9, 52363-40-3
methyl 3-(imidazol-4(5)-yl)-2-propenoate

Conditions

Conditions	Yield
With thionyl chloride	98%
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

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%

: 104-98-3
urocanic acid

: 3718-04-5
4(5)-vinyl imidazole

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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%

: 67-56-1
methanol

: 104-98-3
urocanic acid

: 70346-51-9
(E)-methyl 3-(1H-imidazol-4-yl)acrylate

Conditions

Conditions	Yield
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

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

: 56-35-9
bis(tri-n-butyltin)oxide

: 104-98-3
urocanic acid

: C6H5N2O2(1-)*3C5H11(1-)*Sn(4+)

Conditions

Conditions	Yield
In ethanol; toluene for 24h; Reflux; Dean-Stark;	75%

: 75-89-8
2,2,2-trifluoroethanol

: 104-98-3
urocanic acid

: 2,2,2-trifluoroethyl (E)-3-(1H-imidazol-4-yl)acrylate

Conditions

Conditions	Yield
Stage #1: urocanic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 0.0833333h; Stage #2: 2,2,2-trifluoroethanol In dichloromethane at 20℃; for 18h;	64%

: 104-98-3
urocanic acid

: 71-43-2
benzene

: 3-(1H-imidazole-4-yl)-1-indanone

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid at 80℃; for 18h; Sealed tube; Inert atmosphere;	64%

: 76-87-9
triphenyltin(IV) hydroxide

: 104-98-3
urocanic acid

: C6H5N2O2(1-)*Sn(4+)*3C6H5(1-)

Conditions

Conditions	Yield
In ethanol; toluene for 24h; Reflux; Dean-Stark;	60%

: 7732-18-5
water

: 7646-85-7
zinc(II) chloride

: 104-98-3
urocanic acid

: zinc(II) urocanate hydrate

Conditions

Conditions	Yield
In ethanol; water High Pressure; equimol., heated at 433 K for 72 h; slowly cooled to room temp. (72 h), crysts. collected; elem. anal.;	48%

...Expand

: 174221-86-4
5'-O-dimethoxytrityl-2'-amino-2'-deoxyuridine

: 104-98-3
urocanic acid

: 2'-[3-(imidazol-4-yl)acryloyl]-amido-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyuridine

Conditions

Conditions	Yield
Stage #1: urocanic acid With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; Stage #2: 5'-O-dimethoxytrityl-2'-amino-2'-deoxyuridine In N,N-dimethyl-formamide at 20℃; Further stages.;	45%

: 91970-62-6
benzyl 4-hydroxybutanoate

: 104-98-3
urocanic acid

: C17H18N2O4

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In N,N-dimethyl-formamide at -5 - 20℃; for 12h;	45%

: 3019-04-3
iodoacetone

: 104-98-3
urocanic acid

: 5-[(E)-2-carboxyethenyl]-3-(2-oxopropyl)-1H-imidazol-3-ium triiodide

Conditions

Conditions	Yield
With iodine In neat (no solvent) at 20 - 23℃; for 8h;	25%

: copper(ll) sulfate pentahydrate

: 104-98-3
urocanic acid

: Cu4(5-imidazoleacrylate)6(SO4)*H2O

Conditions

Conditions	Yield
In methanol; water High Pressure; stoich., ligand in CH3OH mixed dropwise with soln. of Cu salt in h2O, heated in an autoclave at 90°C for 3 d; isolated, elem. anal.;	11%

: 947699-91-4
N1-(2-aminoethyl)-N2-(7-chloroquinolin-4-yl)-N1-methylethane-1,2-diamine

: 104-98-3
urocanic acid

: C20H23ClN6O

Conditions

Conditions	Yield
Stage #1: urocanic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide for 2h; Inert atmosphere; Stage #2: N1-(2-aminoethyl)-N2-(7-chloroquinolin-4-yl)-N1-methylethane-1,2-diamine In N,N-dimethyl-formamide for 21h; Inert atmosphere;	8%

: 64-17-5
ethanol

: 541-41-3
chloroformic acid ethyl ester

: 104-98-3
urocanic acid

: 4-(2-ethoxycarbonyl-vinyl)-imidazole-1-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With pyridine In water for 0.0833333h;

...Expand

: 24424-99-5
di-tert-butyl dicarbonate

: 104-98-3
urocanic acid

: 1006066-10-9
3-(1-tert-butoxycarbonyl-imidazol-4-yl)-acrylic acid

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃;

: 104-98-3
urocanic acid

: 112606-55-0
C26H22N2O2

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 98 percent / SOCl2 2: Et3N / dimethylformamide View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid; magnesium sulfate / Reflux 2: triethylamine / N,N-dimethyl-formamide View Scheme

: 104-98-3
urocanic acid

: 226930-86-5
4-chloroallyl-1-tritylimidazole

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 98 percent / SOCl2 2: Et3N / dimethylformamide 3: 75 percent / LiAlH4 / tetrahydrofuran 4: 75 percent / SOCl2 / tetrahydrofuran / 1 h View Scheme

: 104-98-3
urocanic acid

: 500782-79-6
C44H38N4O3

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 98 percent / SOCl2 2: Et3N / dimethylformamide 3: 75 percent / LiAlH4 / tetrahydrofuran 4: 75 percent / SOCl2 / tetrahydrofuran / 1 h 5: 21 percent / NaH / tetrahydrofuran / 2 h / 60 °C View Scheme

: 104-98-3
urocanic acid

: 500782-80-9
C36H36N4O

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 98 percent / SOCl2 2: Et3N / dimethylformamide 3: 75 percent / LiAlH4 / tetrahydrofuran 4: 75 percent / SOCl2 / tetrahydrofuran / 1 h 5: 21 percent / NaH / tetrahydrofuran / 2 h / 60 °C 6: 99 percent / H2 / Pd/C / methanol; ethyl acetate / atmospheric pressure View Scheme

: 104-98-3
urocanic acid

: 500782-81-0
C44H49N5O4

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 98 percent / SOCl2 2: Et3N / dimethylformamide 3: 75 percent / LiAlH4 / tetrahydrofuran 4: 75 percent / SOCl2 / tetrahydrofuran / 1 h 5: 21 percent / NaH / tetrahydrofuran / 2 h / 60 °C 6: 99 percent / H2 / Pd/C / methanol; ethyl acetate / atmospheric pressure 7: 85 percent / CH2Cl2 / 5 h / 0 - 20 °C View Scheme

: 104-98-3
urocanic acid

: 501010-03-3
C25H35N5O4

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 98 percent / SOCl2 2: Et3N / dimethylformamide 3: 75 percent / LiAlH4 / tetrahydrofuran 4: 75 percent / SOCl2 / tetrahydrofuran / 1 h 5: 21 percent / NaH / tetrahydrofuran / 2 h / 60 °C 6: 99 percent / H2 / Pd/C / methanol; ethyl acetate / atmospheric pressure 7: 85 percent / CH2Cl2 / 5 h / 0 - 20 °C 8: 90 percent / TFA; triethylsilane / CH2Cl2 / 1 h / 20 °C View Scheme

Yield

Multi-step reaction with 8 steps
1: 98 percent / SOCl2
2: Et3N / dimethylformamide
3: 75 percent / LiAlH4 / tetrahydrofuran
4: 75 percent / SOCl2 / tetrahydrofuran / 1 h
5: 21 percent / NaH / tetrahydrofuran / 2 h / 60 °C
6: 99 percent / H2 / Pd/C / methanol; ethyl acetate / atmospheric pressure
7: 85 percent / CH2Cl2 / 5 h / 0 - 20 °C
8: 90 percent / TFA; triethylsilane / CH2Cl2 / 1 h / 20 °C
View Scheme

: 104-98-3
urocanic acid

: C24H33N5O4

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 98 percent / SOCl2 2: Et3N / dimethylformamide 3: 75 percent / LiAlH4 / tetrahydrofuran 4: 75 percent / SOCl2 / tetrahydrofuran / 1 h 5: 21 percent / NaH / tetrahydrofuran / 2 h / 60 °C 6: 99 percent / H2 / Pd/C / methanol; ethyl acetate / atmospheric pressure 7: 85 percent / CH2Cl2 / 5 h / 0 - 20 °C 8: 90 percent / TFA; triethylsilane / CH2Cl2 / 1 h / 20 °C 9: 85 percent / aq. NaOH / methanol / 1 h / 20 °C View Scheme

Yield

Multi-step reaction with 9 steps
1: 98 percent / SOCl2
2: Et3N / dimethylformamide
3: 75 percent / LiAlH4 / tetrahydrofuran
4: 75 percent / SOCl2 / tetrahydrofuran / 1 h
5: 21 percent / NaH / tetrahydrofuran / 2 h / 60 °C
6: 99 percent / H2 / Pd/C / methanol; ethyl acetate / atmospheric pressure
7: 85 percent / CH2Cl2 / 5 h / 0 - 20 °C
8: 90 percent / TFA; triethylsilane / CH2Cl2 / 1 h / 20 °C
9: 85 percent / aq. NaOH / methanol / 1 h / 20 °C
View Scheme

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 NO_x.

Product Name

Urocanic acid

Synthetic route

UROCANIC ACID Chemical Properties

UROCANIC ACID History

UROCANIC ACID Toxicity Data With Reference

UROCANIC ACID Consensus Reports

UROCANIC ACID Safety Profile

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