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| Other Sizes |
| Targets |
4-Pentynoic acid does not have a defined pharmacological receptor target in the classical sense. Its primary reported biological activity is as a hypoglycemic agent, which is associated with its ability to elevate hepatic tyrosine aminotransferase and plasma corticosterone levels in rats. It has also been shown to inhibit the growth of prostate cancer cells and to inhibit the production of brain natriuretic peptide (BNP), a predictor of cardiovascular disease. Furthermore, it has regulatory effects on the cellular uptake of calcium carbonate.
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| ln Vitro |
In vitro, 4-Pentynoic acid serves as a key intermediate for producing biologically active compounds. It is used to synthesize ynenol lactones via reactions with 1-bromo-1-alkynes in the presence of a palladium catalyst. It is also employed in the synthesis of cytotoxic macrolides through ring-closing metathesis of bis acetylenes. Its structural similarity to 2,5-dihydroxybenzoic acid allows it to form covalent linkages with iron oxides, leading to particle formation. However, specific IC₅₀ values for its direct activity are not well-characterized in the literature.
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| ln Vivo |
In vivo, 4-Pentynoic acid acts as a hypoglycemic agent, decreasing blood sugar levels in rats. This effect is accompanied by an increase in liver tyrosine aminotransferase activity and plasma corticosterone concentrations. The increase in tyrosine aminotransferase is dependent on the presence of the adrenal glands, as the effect is not observed in adrenalectomized rats. Additionally, it has been reported to inhibit the growth of prostate cancer cells in preclinical models.
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| Enzyme Assay |
The primary non-cellular assay for 4-Pentynoic acid involves measuring its effect on hepatic tyrosine 2-oxoglutarate aminotransferase activity in rat liver homogenates. This assay typically involves administering the compound to rats, sacrificing the animals, and measuring the enzyme activity in liver samples. Other biochemical characterizations include assessing its reactivity in click chemistry applications, such as the CuAAc reaction with azide-bearing compounds. Its ability to form ynenol lactones in palladium-catalyzed reactions can also be used to study its chemical properties.
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| Cell Assay |
No specific cell-based pharmacological assays are routinely performed with 4-Pentynoic acid as a primary test article. However, it may be used as a chemical tool in cell culture to study the effects of its derivatives or as a precursor for synthesizing compounds that are subsequently evaluated for biological activity. Its primary role in a research setting is as a synthetic building block rather than a directly testable pharmacological agent in cell-based assays.
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| Animal Protocol |
In vivo animal studies with 4-Pentynoic acid primarily involve its administration to rats to evaluate its hypoglycemic effects. In these studies, the compound is typically administered, and subsequent measurements are taken for blood glucose levels, liver tyrosine aminotransferase activity, and plasma corticosterone concentrations. Such experiments have demonstrated that 4-Pentynoic acid decreases blood sugar while increasing liver enzyme activity and plasma corticosterone. The effect on tyrosine aminotransferase is dependent on the presence of the adrenal glands.
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| ADME/Pharmacokinetics |
Specific pharmacokinetic (PK) data for 4-Pentynoic acid are not well-documented in the available literature. As a small, polar, water-soluble carboxylic acid (LogP ~0.43), it is expected to be readily absorbed and distributed. It is soluble in water and low-polarity organic solvents. For in vivo formulation, it can be dissolved in a mixture of 10% DMSO, 40% PEG300, 5% Tween 80, and 45% saline. However, comprehensive PK parameters such as half-life, volume of distribution, and clearance have not been reported.
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| Toxicity/Toxicokinetics |
4-Pentynoic acid is classified as a corrosive material and poses significant health hazards. It causes severe skin burns and eye damage (H314). It is harmful if swallowed, in contact with skin, or if inhaled (H302, H312, H332). It may also cause respiratory irritation. Symptoms of overexposure may include headache, dizziness, tiredness, nausea, and vomiting. Appropriate personal protective equipment, including gloves and eye/face protection, should be worn when handling this compound.
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| References |
[1]. Elgafi, et al. Cyclization of acetylenic carboxylic acids and acetylenic alcohols to oxygen-containing heterocycles using cationic rhodium(I) complexes. Journal of Organometallic Chemistry.Volume: 607.Issue: 1-2.Pages: 97-104.Journal 2000.
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| Additional Infomation |
structure
4-Pentynoic acid is a research chemical and is not an approved pharmaceutical drug. Its primary value lies in its role as a versatile intermediate for synthesizing biologically active compounds, including ynenol lactones and cytotoxic macrolides. Its hypoglycemic activity has been demonstrated in animal models, but it has not been developed as a therapeutic agent. It is also used as a building block for sequence-defined oligomers and as a click chemistry reagent. The compound is for research use only and is not intended for human therapeutic or diagnostic use. |
| Molecular Formula |
C5H6O2
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|---|---|
| Molecular Weight |
98.10
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| Exact Mass |
98.036
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| CAS # |
6089-09-4
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| PubChem CID |
22464
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| Appearance |
White to light yellow <54°C solid powder,>57°C liquid
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
199.2±0.0 °C at 760 mmHg
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| Melting Point |
54-57 °C(lit.)
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| Flash Point |
90.8±17.3 °C
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| Vapour Pressure |
0.1±0.8 mmHg at 25°C
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| Index of Refraction |
1.462
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| LogP |
0.43
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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 |
2
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| Heavy Atom Count |
7
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| Complexity |
107
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O([H])C(C([H])([H])C([H])([H])C#C[H])=O
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| InChi Key |
MLBYLEUJXUBIJJ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C5H6O2/c1-2-3-4-5(6)7/h1H,3-4H2,(H,6,7)
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| Chemical Name |
pent-4-ynoic 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 (1019.37 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.25 mg/mL (12.74 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 12.5 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: ≥ 1.25 mg/mL (12.74 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 12.5 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: ≥ 1.25 mg/mL (12.74 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 | 10.1937 mL | 50.9684 mL | 101.9368 mL | |
| 5 mM | 2.0387 mL | 10.1937 mL | 20.3874 mL | |
| 10 mM | 1.0194 mL | 5.0968 mL | 10.1937 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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