Urocanic acid

Product Name: Urocanic acid
CAS No.: 104-98-3
Chemical Name: Urocanic acid
Synonyms: 4-IMIDAZOLEACRYLIC ACID;(E)-3-(1H-imidazol-5-yl)acrylic acid;3-(1H-IMIDAZOL-4-YL)ACRYLIC ACID;SKL080;UROCANIC ACID;Urocanic caid;Urocalic acid;urocanoic acid;UROCANINIC ACID;Urocanic acid,99%
CBNumber: CB8750635
Molecular Formula: C6H6N2O2
Formula Weight: 138.12
MOL File: 104-98-3.mol

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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
pka: 2.94±0.10(Predicted)
form: Powder
color: White to beige
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)
EPA Substance Registry System: 2-Propenoic acid, 3-(1H-imidazol-4-yl)- (104-98-3)

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Safety

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

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 859796
Product name: 4-Imidazoleacrylic acid
Purity: 99%
Packaging: 5g
Price: $54.3
Updated: 2024/03/01

Sigma-Aldrich

Product number: 859796
Product name: 4-Imidazoleacrylic acid
Purity: 99%
Packaging: 25g
Price: $258
Updated: 2024/03/01

Sigma-Aldrich

Product number: 859796
Product name: 4-Imidazoleacrylic acid
Purity: 99%
Packaging: 100g
Price: $813
Updated: 2024/03/01

TRC

Product number: U847063
Product name: UrocanicAcid
Packaging: 250mg
Price: $50
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FU29984
Product name: Urocanic acid
Packaging: 5G
Price: $50
Updated: 2021/12/16

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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.]

Urocanic acid Preparation Products And Raw materials

Raw materials

Hydrogen Sulfide PICRIC ACID Ammonium hydroxide Piperidine Manganese dioxide Formaldehyde D(-)-Fructose Benzene Hydrochloric acid Copper(II) sulfate Pyridine Isopropyl alcohol Malonic acid Sodium carbonate

Preparation Products

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View Lastest Price from Urocanic acid manufacturers

Hebei Weibang Biotechnology Co., Ltd

Product: Urocanic acid 104-98-3
Price: US $0.00-0.00/KG
Min. Order: 50KG
Purity: 99%
Supply Ability: 500000kg
Release date: 2022-09-29

Hebei Mojin Biotechnology Co., Ltd

Product: Urocanic acid 104-98-3
Price: US $0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 50000KG/month
Release date: 2023-11-13

104-98-3, Urocanic acidRelated Search:

Citric acid Ethyl acrylate Folic acid Acrylic acid Stearic acid Methyl methacrylate Methyl acrylate Methacrylic acid Poly(acrylic acid) Butyl acrylate 6-Benzylaminopurine Ethyl 2-(Chlorosulfonyl)acetate Hyaluronic acid Ursolic acid Ascoric Acid ETHOXYLATED BISPHENOL A DIACRYLATE SODIUM UROCANATE Urocanic acid ethyl

(E)-3-(3H-imidazol-4-yl)acrylic acid

3-(1H-imidazol-4-yl)prop-2-enoic acid

3-(3H-imidazol-4-yl)acrylic acid

1H-Imidazole-4-acrylic acid

1H-Imidazole-5-acrylic acid

Urocanic acid,99%

4-Imidazoleacrylic acid,3-(4-Imidazolyl)acrylic acid, Urocanic acid

(E)-3-(1H-Imidazol-5-yl)-2-propenoic acid

Urocanic acid, 99% 25GR

2-Propenoic acid,3-(1H-iMidazol-5-yl)-

4-IMidazoleacrylic acid 99%

trans-Urocanic Acid , 98.0%(LC&T

3-(1H-IMIDAZOL-4-YL)ACRYLIC ACID

3-(4-IMIDAZOLY)ACRYLIC ACID

3,4-IMIDAZOLYLACRYLIC ACID

4-IMIDAZOLEACRYLIC ACID

(E)-3-(1H-IMIDAZOL-4-YL)-ACRYLIC ACID

IMIDAZOLE-4-ACRYLIC ACID

B 4(5)-GLYOXALINYLACRYLIC ACID

RARECHEM AL BK 0762

TIMTEC-BB SBB006702

UROCANIC ACID

UROCANINIC ACID

2-Propenoic acid, 3-(1H-imidazol-4-yl)-

3-(3H-imidazol-4-yl)prop-2-enoic acid

UROCANIC ACID 99%

Urocanic caid

1H-Imidazole-4-acrylic acid (Urocanic acid)

urocanoic acid

3-(4-Imidazolyl)acrylic acid, Urocanic acid

Urocalic acid

4-IMIDAZOLEacrylic acid: 3-(4-imidazolyl)acrylic acid

(E)-3-(1H-imidazol-5-yl)acrylic acid

3-(1H-Imidazol-4-yl)

Imidazole-4-acrylic acid for synthesis

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

Histidine metabolism

3-imi dazo1-4-ylaery1i c acid

4-Imidazolylacrylic acid

4-lmidazdeacrylic acid

SKL080

(Z)-3-(1H-imidazol-5-yl)prop-2-enoic acid

3-(1H-imidazol-5-yl)acrylic acid

Urinary acid Reference Standards

104-98-3

104-93-3

104-98-03

C6H6N2O22H2O

CARBOXYLIC ACID

Heterocyclic Building Blocks

Imidazoles

Building Blocks

Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines