3D Mol Similar

Urocanic acid

: Iupac Name：(E)-3-(1H-imidazol-5-yl)prop-2-enoic acid; CAS No.: 104-98-3; Molecular Weight：138.12404; Modify Date.: 2023-02-17 04:06; Introduction:
Urocanic acid, produced in the upper layers of mammalian skin, is a major absorber of ultraviolet radiation (UVR).
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1. Names and Identifiers

: 1.1 Name; Urocanic acid; 1.2 Synonyms; (2E)-3-(1H-Imidazol-4-yl)acrylic acid (2E)-3-(1H-imidazol-4-yl)acrylic acid hydrate (2E)-3-(1H-Imidazol-4-yl)acrylic acid hydrate (1:1) (2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid (2E)-3-(1H-Imidazol-5-yl)acrylic acid (E)-3-(1H-imidazol-4-yl)-2-propenoic acid (E)-3-(1H-imidazol-4-yl)acrylic acid (E)-3-(1H-Imidazol-5-yl)-2-propenoic acid (E)-3-(3H-imidazol-4-yl)acrylic acid (Z/E)-3-(1H-imidazol-4-yl)-2-propenoic acid 1H-Imidazole-4-acrylic acid 1H-Imidazole-5-acrylic acid 2-Propenoic acid, 3-(1H-imidazol-4-yl)-, (2E)- 2-Propenoic acid, 3-(1H-imidazol-4-yl)-, (2E)-, hydrate (1:1) 2-propenoic acid, 3-(1H-imidazol-4-yl), (2E), monohydrate 2-propenoic acid, 3-(1H-imidazol-4-yl)-, (2E)-, monohydrate 2-propenoic acid, 3-(1H-imidazol-5-yl)-, (2E)- 3-(1H-Imidazol-4-yl)acrylic acid 3-(1H-imidazol-4-yl)prop-2-enoic acid 3-(3H-imidazol-4-yl)acrylic acid 3-imidazol-4-ylacrylic 3-imidazol-4-yl-acrylic acid 4-imidazoleacrylate 4-Imidazoleacrylic Acid 4-Imidazoleacrylic acid,3-(4-Imidazolyl)acrylic acid, Urocanic acid EINECS 203-258-4 imidazoleacrylicacid MFCD00005203 RARECHEM AL BK 0762 Trans-Urocanic acid Urocanate Urocanic caid UROCANINIC ACID urocanoic acid urosanic acid; View all

1.3 CAS No.: 104-98-3

1.4 CID: 736715

1.5 EINECS(EC#): 203-258-4

1.6 Molecular Formula: C6H6N2O2 (isomer)

1.7 Inchi: InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1+

1.8 InChIkey: LOIYMIARKYCTBW-OWOJBTEDSA-N

1.9 Canonical Smiles: C1=C(NC=N1)C=CC(=O)O

1.10 Isomers Smiles: C1=C(NC=N1)/C=C/C(=O)O

2. Properties

2.1 Density: 1.43

2.1 Melting point: 226-228 °C(lit.)

2.1 Boiling point: 456.9 °C at 760 mmHg

2.1 Refractive index: 1.5100 (estimate)

2.1 Flash Point: 230.1 °C

2.1 Precise Quality: 138.04300

2.1 PSA: 65.98000

2.1 logP: 0.50750

2.1 Solubility: 1.5g/l

2.2 Appearance: Solid

2.3 Storage: 2-8°C

2.4 Chemical Properties: white to beige fine powder

2.5 Color/Form: White to beige

2.6 pKa: 2.94±0.10(Predicted)

2.7 Water Solubility: 1500 mg/L (at 17 °C)

2.8 Stability: Stable under normal temperatures and pressures.

2.9 StorageTemp: Keep in dark place,Sealed in dry,2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: 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.

3.2 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

4. Safety and Handling

4.1 Risk Statements: S22-S24/25

4.1 Safety Statements: 22-24/25

4.1 Hazard Class: IRRITANT

4.1 RIDADR: NONH for all modes of transport

4.1 WGK Germany: 3

4.1 RTECS: NI3425200

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

4.2 Specification: white to beige fine powder
Safety Statements:22-24/25
22:Do not breathe dust
24/25:Avoid contact with skin and eyes

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s)	no data available
Signal word	no data available
Hazard statement(s)	no data available
Precautionary statement(s)
Prevention	no data available
Response	no data available
Storage	no data available
Disposal	no data available

2.3 Other hazards which do not result in classification

no data available

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6. Synthesis Route

104-98-3Total: 1 Synthesis Route

71-00-1 406 Suppliers

104-98-3 44 Suppliers

Literatures:
Analytical Chemistry, , vol. 77, # 4 p. 1013 - 1019
Yield: null

7. Precursor and Product

precursor:

71-00-1

product :

49549-75-9

56662-92-1

8. Other Information

8.0 Manufacturing Info: 2-Propenoic acid, 3-(1H-imidazol-5-yl)-: ACTIVE

8.1 BRN: 81405

8.2 体外研究: 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.

8.3 Chemical Properties: white to beige fine powder

8.4 Uses: Urocanic Acid is a biomarker in the fecal metabolic profiling of breast cancer patients.

8.5 Definition: ChEBI: 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.

8.6 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.

9. Computational chemical data

Molecular Weight: 138.12404g/mol
Molecular Formula: C₆H₆N₂O₂
Compound Is Canonicalized: True
XLogP3-AA: 0
Exact Mass: 138.042927438
Monoisotopic Mass: 138.042927438
Complexity: 156
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 66
Heavy Atom Count: 10
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcYBjMAAAAAAAAAAAAAAAAAAAAWAAAAAAAAAAAAAAAAABgAAAHgAQCAAACAjBlgQtmBbJkgCoATT3bACCgC2xEqAJ2YA4cFiITADACQAUEAAIEAJIkaYAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10. Recommended Suppliers

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4-Imidazoleacrylic acid

Purity:99%Packing: 200kg/bag FOB
Price: 3 USD/kilogram
Time: 2023/09/27

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Nanjing Chemlin Chemical Co., Ltd. Diamond member

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Urocanic acid