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Purity: ≥98%
Phloretin (also known as NSC 407292 and RJC 02792), a naturally occuring dihydrochalcone flavonoid mainly found in fruit, leaves, and roots of apple tree, inhibits a variety of transporters such as the monocarboxylate transporters MCT1 and MCT2 (IC50 = 28 and 14 µM, respectively). Phloretin has anti-inflammatory, anti-tumor, and antioxidant properties in mammalian cells. Phloretin(NSC 407292; RJC 02792) is a dihydrochalcone, a type of natural phenols. Phloretin blocks SGLT1 and SGLT2's ability to actively transport glucose into cells.
| Targets |
SGLT1; SGLT2; Microbial Metabolite; GLUT1; GLUT2
Phloretin-sensitive urea transporters (specifically, UT-A1 and UT-A3 isoforms expressed in the inner medullary collecting duct, IMCD). The literature uses Phloretin as an inhibitor to demonstrate the presence and function of these facilitated urea transporters. [4] |
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| ln Vitro |
Phloretin is a dihydrochalcone that can be found in the bark of fruit trees such as cherries, apples, and pears (Pyrus communis). Phloretin, like its glycoside phlorizin, inhibits the active transport of glucose into cells by SGLT1 and SGLT2, albeit to a lesser extent. [1] In the small intestine, hydrolytic enzymes convert nearly all of the phlorizin taken orally into phloretin. An important effect of this is the inhibition of glucose absorption by the small intestine and the inhibition of renal glucose reabsorption. [2] [3] Additionally, a number of urea transporters are inhibited by phenyletin. When used in conjunction with diets high in protein, it causes diuresis and urea loss. [4]
In isolated perfused inner medullary collecting ducts (IMCDs) from wild-type mice, the addition of 0.25 mM Phloretin (in the presence of 0.1 nM arginine vasopressin, AVP) to both the apical and basolateral sides of the tubules resulted in a significant decrease in urea permeability (Purea). This inhibition confirmed that the AVP-stimulated increase in Purea was mediated by phloretin-sensitive urea transporters. In contrast, in IMCDs from UT-A1/3-/- mice (lacking UT-A1 and UT-A3), the low basal Purea was not inhibited by Phloretin, indicating the absence of these specific transporters. [4] The study establishes that Phloretin is an effective inhibitor of facilitated, vasopressin-regulated urea transport mediated by UT-A1 and UT-A3 in the IMCD. [4] |
| ln Vivo |
Phloretin (methanol; 50 or 100 mg/kg; once daily) reduces hydrogen peroxide and malondialdehyde (MDA) and hydrogen peroxide (H2O2) levels in paw tissue and reduces anticollagen efficacy in serum [animal model : Collagen-induced arthritis (CIA) mice [3] Dosage: 50 or 100 mg/kg Administration method: Oral Results: Compared with traditional drugs, in addition to reducing inflammation in the hind limbs, it also showed relief from clinical symptoms of RA. 3]. control group.
When male Wistar rats were fed a single meal containing Phloretin (0.157% in diet, providing 22 mg phloretin equivalents), the unconjugated (aglycone) form of Phloretin was detected in plasma at 4, 10, and 24 hours post-feeding, alongside its conjugated (glucuronidated and/or sulfated) metabolites. The absorption kinetics differed when comparing aglycone vs. glucoside (phloridzin) administration; Phloretin appeared more rapidly in plasma when administered as the aglycone than as phloridzin. However, total plasma concentrations of phloretin (sum of conjugated and unconjugated) at 10 hours post-feeding were not significantly different between the two forms. By 24 hours, plasma concentrations returned to near baseline levels. [3] Ingestion of Phloretin (22 mg) in a meal did not significantly increase glucosuria in non-diabetic rats compared to controls when measured 10 hours post-feeding. [3] |
| Cell Assay |
Cell Line: BEL-7402 cell
Concentration: 40-160 μM Incubation Time: 24 hours Result: Induced cell apoptosis and activated caspase 3, 6 and 9. |
| Animal Protocol |
Collagen-Induced Arthritis (CIA) Mice
50 or 100 mg/kg Oral adminstration Bioavailability Study in Rats: Male Wistar rats (~160 g) were housed individually in metabolic cages. After 14 days on a control diet, they were divided into groups and fed a single 20 g experimental meal. One group received the control diet supplemented with 0.157% Phloretin (providing 22 mg phloretin equivalents). Food intake was monitored. At 4, 10, and 24 hours after the start of the meal, groups of rats (n=6 per time point) were anesthetized with sodium pentobarbital (40 mg/kg body weight). Blood was collected from the abdominal aorta into heparinized tubes, and plasma was separated. Urine was collected over a 24-hour period. Plasma samples were acidified and stored at -20°C until analysis. [3] |
| ADME/Pharmacokinetics |
Metabolites/Metabolic Substances Known metabolites of phlorizin include phlorizin-4-hydroxy-glucuronide and phlorizin-2-hydroxy-glucuronide. Absorption: Phlorizin is absorbed from the diet. When administered in aglycone form, it appears in plasma more rapidly than when administered in glucosinolate (phlorizin) form. No intact phlorizin was detected in plasma, indicating that it was hydrolyzed prior to absorption (likely by lactase-phlorizin hydrolase, LPH). [3] Plasma Metabolites: In rats fed phlorizin, the compound was present primarily in bound form (glucuronide and/or sulfate), accounting for 85-95% of total circulating phlorizin after 4 hours. The remaining 5-15% was present in unbound phlorizin form. Methoxylated form was not detected. [3]
Plasma Concentration: After ingestion of food containing phlorizin (0.157%), the total plasma phlorizin concentration peaked at 4 hours (22.8 ± 2.8 µmol/L), decreased after 10 hours, and returned to near baseline levels (4.8 ± 2.1 µmol/L) after 24 hours. [3] Excretion: After ingestion of food containing phlorizin, the cumulative excretion of phlorizin (bound and unbound) in urine over 24 hours was 8.5 ± 0.9 µmol. This is equivalent to approximately 10.4% of the ingested dose. [3] Elimination: Within 24 hours of ingestion, the plasma concentration of phlorizin metabolites decreased rapidly, indicating that it is mainly eliminated through urine, with limited enterohepatic circulation compared to some other flavonoids. [3] |
| References | |
| Additional Infomation |
Phlorizin is a dihydrochalcone compound with a structure of dihydrochalcone substituted with hydroxyl groups at the 4, 2', 4' and 6' positions. It is a plant metabolite and antitumor drug that is functionally related to dihydrochalcone. Phlorizin is a natural dihydrochalcone found in apples and many other fruits. Phlorizin has been reported in apples, turmerics and other organisms with relevant data. Phlorizin is a natural dihydrochalcone found in apples and many other fruits. Phlorizin has been shown in the literature to be an inhibitor of urea facilitated transport. [4] In in vitro perfusion tubule experiments, the use of 0.25 mM phlorizin was crucial for distinguishing urea transport mediated by a specific UT-A transporter from simple lipid diffusion. [4] This study utilized the known pharmacological properties of phlorizin in inhibiting urea transporters as a tool to validate the UT-A1/3 knockout mouse phenotype and understand the physiology of renal concentration mechanisms. [4]
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| Molecular Formula |
C15H14O5
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|---|---|
| Molecular Weight |
274.2687
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| Exact Mass |
274.084
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| Elemental Analysis |
C, 65.69; H, 5.15; O, 29.17
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| CAS # |
60-82-2
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| PubChem CID |
4788
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| Appearance |
Off-white to pink solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
534.4±29.0 °C at 760 mmHg
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| Melting Point |
~260 °C
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| Flash Point |
291.1±20.8 °C
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| Vapour Pressure |
0.0±1.5 mmHg at 25°C
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| Index of Refraction |
1.685
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| LogP |
3.5
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
20
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| Complexity |
312
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C(C1C(=C([H])C(=C([H])C=1O[H])O[H])O[H])C([H])([H])C([H])([H])C1C([H])=C([H])C(=C([H])C=1[H])O[H]
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| InChi Key |
VGEREEWJJVICBM-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C15H14O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-2,4-5,7-8,16-17,19-20H,3,6H2
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| Chemical Name |
3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
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| Synonyms |
RJC 02792; NSC 407292; NSC-407292; NSC407292; RJC02792; RJC-02792; Phloretin
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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: 50~55 mg/mL (182.3~200.5 mM)
Ethanol: ~55 mg/mL |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.12 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 (9.12 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 (9.12 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: 5%DMSO + Corn oil: 0.45mg/ml (1.64mM) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.6460 mL | 18.2302 mL | 36.4604 mL | |
| 5 mM | 0.7292 mL | 3.6460 mL | 7.2921 mL | |
| 10 mM | 0.3646 mL | 1.8230 mL | 3.6460 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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