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
• NACRES: NA.77
• PubChem Substance ID: 24278652
• UNSPSC Code: 12352202
• EC Number: 200-488-7
• MDL number: MFCD00002288
• Beilstein/REAXYS Number: 1887240
• Assay: ≥99%
• Form: powder

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

Major polyphenol found in apple; aglycone of phloridzin.

Phloretin a polar dye belongs to the class of dihydrochalcones.

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.

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

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.

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: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)