Human Endogenous Metabolite

Toxicity Summary
Identification and Uses: 2(5H)-furanone is an endogenous satiety agent that suppresses appetite and/or food intake. Animal models suggest that 2-furanone may be a promising treatment for obesity and autoimmune diseases. Human Exposure and Toxicity: 2-furanone and 2-pyranone induce cellular DNA damage and form topoisomerase I-DNA and topoisomerase II-DNA complexes within cells. Both lactones are cytotoxic to human cell lines: their toxic concentrations are lower in A549 lung cancer cells than in MRC5 non-malignant lung fibroblasts. These results suggest that 2-furanone and 2-pyranone may possess anticancer and DNA-damaging activities. Animal Toxicity Studies: To investigate the effects of 2-furanone on food intake, Wistar rats underwent various administration treatments. Intraperitoneal injection of 2-furanone at doses ranging from 30 to 100 mg/kg doses dose-dependently reduced food intake but had no significant effect on drinking patterns or locomotor activity. Intragastric perfusion and intraventricular injection of 2-furanone also reduced food intake in a dose-dependent manner. In other studies, researchers tested the effects of 2-furanone on feeding behavior in rhesus monkeys. They implanted catheters into the third ventricle of three adult male rhesus monkeys. On different dates, different doses of 2-furanone were injected intraventricularly five minutes before food presentation. The effective dose inducing a significant satiety effect was 20.0 mg, while 10.6 mg induced a mild satiety effect, and 25.0 mg induced a severe satiety effect. This study suggests that 2-furanone may have a satiety mechanism in monkeys and rats. Intraperitoneal injection of 2-furanone (5 mg/kg) improved spatial cognitive ability in mice. In addition, 2-furanone also suppressed the clinical symptoms of experimental allergic encephalomyelitis in Lewis rats (a human multiple sclerosis model induced by myelin basic protein (MBP) immunity). Following MBP immunization, rats treated with 2-furanone showed a reduced delayed-type hypersensitivity to MBP. These results indicate that 2-furanone is not only a potent satiating agent but also effectively promotes memory and regulates immune function.

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Interactions
Intraperitoneal injection of 2-deoxy-D-glucose (2-DG) dose-dependently increased gastric acid secretion, and this change was consistent with changes in the activities of gastric choline acetyltransferase (CAT) and acetylcholinesterase (AChE). Double reciprocal plot analysis of the 2-DG-induced increases in CAT and AChE activity indicated that these changes were due to an increase in the maximum reaction rate (Vmax), while the substrate Michaelis constant (Km) remained unchanged. Uptake of [³H]choline and subsequent synthesis of [³H]acetylcholine (ACh) were observed in the foregut, gastric body, antrum, and duodenum. 2-Deoxy-D-glucose significantly increased the uptake of [³H]choline and the synthesis of [³H]ACh in all gastric regions and the duodenum in a dose-dependent manner. The 2-DG-induced increase in gastric acid secretion occurred synchronously with the early uptake of [(3)H]choline and the synthesis of [(3)H]acetylcholine. 2-DG had little effect on the conversion of taken-up [(3)H]choline to [(3)H]acetylcholine. The levels of acetylcholine and choline, as well as the turnover rate of acetylcholine, remained unchanged after 2-DG administration. 2-Buten-4-lactone (2-B4O) inhibited vagal nerve activity through the central nervous system, preventing 2-DG-induced [(3)H]choline uptake and subsequent [(3)H]acetylcholine synthesis, as well as increased gastric acid secretion. These results suggest that [(3)H]choline uptake and subsequent [(3)H]ACh synthesis are closely related to vagal neuronal activity, and that cholinergic neuronal activity depends on quantitative changes in ACh metabolism in the gastroduodenal region.

Buten-2-lactone is a butenolactone. It is a tautomer of buten-3-lactone. 2(5H)-furanone has been reported in tea (Camellia sinensis), Fusarium graminearum, and other organisms with relevant data. See also: Butenolactone (note moved to).

C4H4O2

84.07

84.021

497-23-4

10341

Colorless to light yellow liquid

1.2±0.1 g/cm3

203.7±0.0 °C at 760 mmHg

4-5 °C ; 4.5 °C

101.1±0.0 °C

0.3±0.4 mmHg at 25°C

1.481

-0.84

0

2

0

6

93.7

0

O1C(C([H])=C([H])C1([H])[H])=O

VIHAEDVKXSOUAT-UHFFFAOYSA-N

InChI=1S/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2

2H-furan-5-one

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO: 100 mg/mL (1189.48 mM)

Solubility in Formulation 1: ≥ 2.5 mg/mL (29.74 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 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.

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Solubility in Formulation 2: ≥ 2.5 mg/mL (29.74 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 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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (29.74 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
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 corn oil and mix evenly.

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 (Please use freshly prepared in vivo formulations for optimal results.)