| Size | Price | Stock | Qty |
|---|---|---|---|
| 1g |
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| Other Sizes |
| Targets |
Human Endogenous Metabolite
trans-Urocanic acid targets the skin's immune system and acts as a photoreceptor. Upon exposure to UV radiation, trans-UCA isomerizes to cis-urocanic acid, which has immunosuppressive properties. The compound is involved in the regulation of cutaneous immune responses and may interact with various immune cells including Langerhans cells and T cells. Its "target" is the immune system and photobiological pathways. |
|---|---|
| ln Vitro |
Trans-urocanic acid (trans-UCA) diminishes NK cell activation mediated by IL-2 and partially inhibits the cytotoxic action of NK cells that have been activated by IL-2[1]. Trans-urocanic acid (trans-UCA; 100 μg/mL) marginally reduces primary human keratinocyte viability and cell proliferation[2].
In vitro, trans-Urocanic acid is used to study its photoisomerization to cis-urocanic acid and its effects on immune cell function. It has been shown to modulate cytokine production, inhibit T cell proliferation, and affect antigen presentation. Its activity is primarily related to its role as a UV-absorbing chromophore and its immunomodulatory effects following photoisomerization. |
| ln Vivo |
In vivo, trans-Urocanic acid is a major UV-absorbing compound in the stratum corneum and plays a role in photoprotection of the skin. Upon UV exposure, it isomerizes to cis-urocanic acid, which has immunosuppressive properties. This photoisomerization is involved in the regulation of cutaneous immune responses and may contribute to UV-induced immunosuppression and skin cancer development.
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| Enzyme Assay |
In vitro enzyme assays with trans-Urocanic acid typically involve studying the enzyme histidase, which catalyzes the formation of urocanic acid from histidine. The compound can also be used in assays to study its photoisomerization upon UV irradiation. Standard assays involve incubating the compound with enzyme preparations or UV light and analyzing the products by HPLC or spectrophotometry.
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| Cell Assay |
Cell Proliferation Assay[2]
Cell Types: Primary human keratinocytes Tested Concentrations: 100 μg/mL Incubation Duration: 24 hrs (hours) Experimental Results: diminished cell proliferation and viability. In vitro cell culture experiments with trans-Urocanic acid involve treating immune cells such as Langerhans cells, dendritic cells, or T cells with the compound or its cis-isomer. Cells are treated with various concentrations, and endpoints include assessment of cytokine production, cell proliferation, and activation markers. These experiments characterize the immunomodulatory effects of urocanic acid isomers. |
| Animal Protocol |
In vivo animal experiments with trans-Urocanic acid typically involve exposing animals to UV radiation and measuring the levels of trans- and cis-urocanic acid in the skin. Alternatively, the compound or its isomers are administered topically or systemically to study their effects on immune responses. These studies are used to understand the role of urocanic acid in photoprotection and UV-induced immunosuppression.
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| ADME/Pharmacokinetics |
The pharmacokinetic (PK) properties of trans-Urocanic acid reflect its role as a skin metabolite. It is synthesized in the epidermis from histidine and accumulates in the stratum corneum. Upon UV exposure, it undergoes photoisomerization to cis-urocanic acid. It is not systemically absorbed to a significant extent and is primarily localized in the skin. Its levels in the skin reflect histidine metabolism and UV exposure.
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| Toxicity/Toxicokinetics |
trans-Urocanic acid has a low toxicity profile as it is a naturally occurring skin metabolite. It is not considered a hazardous substance. For research use, standard laboratory safety practices are sufficient. It is a major UV-absorbing compound in the skin and plays a role in photoprotection. Comprehensive toxicology studies have not been published for this compound.
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| References |
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| Additional Infomation |
Urocanic acid is an α,β-unsaturated monocarboxylic acid formed by the substitution of a 2-enoic acid at the 3-position with a 1H-imidazol-4-yl group. It is a metabolite of uridine. It is both a chromophore and a human metabolite. It is an α,β-unsaturated monocarboxylic acid belonging to the imidazole class of compounds. It is the conjugate acid of Urocanic acid. Urocanic acid is a metabolite found or produced in Escherichia coli (K12 strain, MG1655 strain). It has been reported to exist in Homo sapiens, common sponges, and other organisms with relevant data. 4-Imidazole acrylic acid.
trans-Urocanic acid (trans-UCA) is a naturally occurring metabolite formed by the deamination of histidine in the skin. It is a major UV-absorbing compound in the stratum corneum and plays a role in photoprotection. Upon UV exposure, it isomerizes to cis-urocanic acid, which has immunosuppressive properties. The compound is not a drug and has no therapeutic indications. It is available for laboratory research use only. |
| Molecular Formula |
C6H6N2O2
|
|---|---|
| Molecular Weight |
138.12
|
| Exact Mass |
138.042
|
| CAS # |
3465-72-3
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| Related CAS # |
Urocanic acid;104-98-3;cis-Urocanic acid;7699-35-6
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| PubChem CID |
736715
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| Appearance |
Off-white to light yellow solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
456.9±20.0 °C at 760 mmHg
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| Flash Point |
230.1±21.8 °C
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| Vapour Pressure |
0.0±1.2 mmHg at 25°C
|
| Index of Refraction |
1.674
|
| LogP |
0.01
|
| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
2
|
| Heavy Atom Count |
10
|
| Complexity |
156
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| Defined Atom Stereocenter Count |
0
|
| SMILES |
C1=C(NC=N1)/C=C/C(=O)O
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| InChi Key |
LOIYMIARKYCTBW-OWOJBTEDSA-N
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| InChi Code |
InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1+
|
| Chemical Name |
(E)-3-(1H-imidazol-5-yl)prop-2-enoic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: 100 mg/mL (724.01 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (18.10 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (18.10 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (18.10 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 7.2401 mL | 36.2004 mL | 72.4008 mL | |
| 5 mM | 1.4480 mL | 7.2401 mL | 14.4802 mL | |
| 10 mM | 0.7240 mL | 3.6200 mL | 7.2401 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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