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Tiglic acid is an agonist of the free fatty acid receptor 2 (FFA2), also known as GPR43. FFA2 is a G protein-coupled receptor that is activated by short-chain fatty acids and plays a role in metabolic and inflammatory processes. By agonizing FFA2, Tiglic acid can modulate these pathways. It also upregulates the expression of PYY, a peptide hormone that reduces appetite. This suggests a potential role in metabolic disorders such as obesity and diabetes. Its derivatives also exhibit anti-inflammatory activity.
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| ln Vitro |
In vitro, Tiglic acid acts as an agonist of FFA2 and upregulates PYY expression. This activity can be studied in cells expressing FFA2, where the activation of the receptor leads to downstream signaling events. Its derivatives have anti-inflammatory activity, which can be assessed by measuring the production of inflammatory cytokines in stimulated immune cells. It also shows antiviral activity toward herpes simplex virus type 1 in vitro. Quantitative activity data, such as EC50 values for FFA2 activation, is not detailed in the publicly available sources.
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| ln Vivo |
In vivo, Tiglic acid has been studied for its potential in treating obesity, diabetes, and inflammatory diseases. Its ability to upregulate PYY expression suggests it could reduce appetite and food intake. Its anti-inflammatory and antiviral activities also suggest potential therapeutic applications. However, detailed in vivo efficacy studies, including pharmacokinetic and pharmacodynamic parameters, are limited in the available sources. Further research is needed to fully characterize its in vivo activity.
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| Enzyme Assay |
For cell-free enzyme assays, the activity of Tiglic acid at the FFA2 receptor can be studied using GTPγS binding assays. In these assays, membrane preparations from cells expressing FFA2 are incubated with varying concentrations of Tiglic acid and [35S]GTPγS. The amount of bound [35S]GTPγS, which is proportional to receptor activation, is measured. The EC50 value for receptor activation can be calculated. Its anti-inflammatory activity can be assessed using enzyme inhibition assays.
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| Cell Assay |
For in vitro cellular assays, the effect of Tiglic acid on FFA2 activation can be studied in cells expressing the receptor. Cells are treated with varying concentrations of Tiglic acid, and downstream signaling, such as intracellular calcium mobilization or cAMP accumulation, is measured. Its effect on PYY expression can be assessed by treating enteroendocrine cells with the compound and measuring PYY mRNA and protein levels by qPCR and ELISA.
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| Animal Protocol |
For in vivo studies, Tiglic acid could be administered orally or intraperitoneally in rodent models of obesity or diabetes. Its effect on food intake and body weight would be assessed over a period of treatment. Its effect on PYY levels in the blood would be measured by ELISA. In models of inflammation, its anti-inflammatory effect could be assessed by measuring the levels of inflammatory cytokines.
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| ADME/Pharmacokinetics |
Tiglic acid has a molecular formula of C5H8O2 and a molecular weight of 100.12 g/mol. Its CAS number is 80-59-1. It is a colorless to pale yellow liquid. It has a pungent odor and is soluble in organic solvents. For in vitro studies, it is dissolved in DMSO or ethanol. For in vivo administration, it can be formulated in suitable vehicles. Storage is recommended at room temperature, protected from light. Its purity is typically >98% for research use.
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| Toxicity/Toxicokinetics |
No detailed toxicity data is publicly available. Tiglic acid is described as a poisonous liquid, indicating that it requires careful handling. Its safety profile would need to be established through standard toxicological studies. Its use in perfumes and flavoring agents suggests it is used at low concentrations.
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| References | |
| Additional Infomation |
Tiglic acid (corrosive solid) is a white, shiny, flaky solid with a fruity or spicy odor. Its density is similar to water, and it is slightly soluble in water. It may burn when heated to high temperatures. It can severely irritate the skin, eyes, lungs, or mucous membranes. Tiglic acid is a 2-methylbut-2-enoic acid with a trans configuration of its double bonds. It is a plant metabolite functionally related to crotonic acid. Tiglic acid has been reported in Ligularia pleurocaulis, Eryngium foetidum, and other organisms with relevant data. See also: burdock root (partial); coltsfoot root (partial).
Tiglic acid is a research-grade compound and is not approved for any therapeutic use. It serves primarily as a valuable pharmacological tool for studying FFA2 receptor function and metabolic pathways. Its mechanism of action involves the agonism of FFA2 and the upregulation of PYY expression. Its anti-inflammatory and antiviral activities make it a compound of interest for drug discovery. No clinical trials have been reported. |
| Molecular Formula |
C5H8O2
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| Molecular Weight |
100.1158
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| Exact Mass |
100.052
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| CAS # |
80-59-1
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| PubChem CID |
125468
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| Appearance |
White to off-white solid powder
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
198.5±0.0 °C at 760 mmHg
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| Melting Point |
61-64 °C(lit.)
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| Flash Point |
95.9±9.6 °C
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| Vapour Pressure |
0.2±0.7 mmHg at 25°C
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| Index of Refraction |
1.451
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| LogP |
1.35
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
7
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| Complexity |
103
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C/C=C(\C)/C(=O)O
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| InChi Key |
UIERETOOQGIECD-ONEGZZNKSA-N
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| InChi Code |
InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/b4-3+
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| Chemical Name |
(E)-2-methylbut-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 (~998.80 mM)
H2O : ~7.69 mg/mL (~76.81 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (24.97 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 (24.97 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 (24.97 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 15 mg/mL (149.82 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; Need ultrasonic and warming and heat to 54°C. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 9.9880 mL | 49.9401 mL | 99.8801 mL | |
| 5 mM | 1.9976 mL | 9.9880 mL | 19.9760 mL | |
| 10 mM | 0.9988 mL | 4.9940 mL | 9.9880 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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