P7912

Phloretin

≥99% (HPLC), powder, GLUT inhibitor

• Synonym(s): β-(4-Hydroxyphenyl)-2,4,6-trihydroxypropiophenone, 2′,4′,6′-Trihydroxy-3-(4-hydroxyphenyl)propiophenone, 3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanone
• Empirical Formula (Hill Notation): C₁₅H₁₄O₅
• CAS Number: 60-82-2
• Molecular Weight: 274.27
• Beilstein/REAXYS Number: 1887240
• EC Number: 200-488-7
• MDL number: MFCD00002288
• UNSPSC Code: 12352202
• PubChem Substance ID: 24278652
• NACRES: NA.77

Properties

• product name: Phloretin, ≥99%
• assay: ≥99%
• form: powder
• mp: ~260 °C
• storage temp.: 2-8°C
• SMILES string: Oc1ccc(CCC(=O)c2c(O)cc(O)cc2O)cc1
• 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
• InChI key: VGEREEWJJVICBM-UHFFFAOYSA-N

Description

General description

Phloretin a polar dye belongs to the class of dihydrochalcones.

Major polyphenol found in apple; aglycone of phloridzin.

Application

Phloretin has been used:

• to study its effect on the 2-[N-(7-Nitrobenz-2-oxa-1,3-diazol-4-yl)amino]-2-deoxy-d-glucose (2-NBDG) and 2-[N-(7-Nitrobenz-2-oxa-1,3-diazol-4-yl)amino]-2-deoxy-l-glucose (2-NBDLG) uptake
• to incubate microvesicles in order to inhibit GLUT1 (glucose transporter 1)-mediated transport in radioactive ligand up-take assay
• as a component of KRH buffer to stop glucose uptake by trophoblast cells in vitro

Biochem/physiol Actions

Blocks L-type Ca²⁺ channels; activates Ca²⁺-activated K⁺ channels in amphibian myelinated nerve fibers. Monocarboxylate transporter inhibitor.

Phloretin is known to decrease interfacial dipole potential of lipid bilayer. Phloretin possess antitumor action by preventing protein kinase C (PKC) activity and stimulating programmed cell death. It is found to inhibit the transport functions of GLUTs (glucose transporter) and aquaporins.

Reacts with vic-dicarbonyl compounds such as glyoxal and methylglyoxal, preventing cytotoxic conjugation with biological macromolecules.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)