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P7912

Sigma-Aldrich

Phloretin

≥99% (HPLC), powder, GLUT inhibitor

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C15H14O5
Número de CAS:
60-82-2
Peso molecular:
274.27
Beilstein/REAXYS Number:
1887240
EC Number:
200-488-7
MDL number:
MFCD00002288
UNSPSC Code:
12352202
PubChem Substance ID:
24278652
NACRES:
NA.77

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

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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.

pictograms

Exclamation mark
GHS07

signalword

Warning

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)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Modulation of lipid bilayer interfacial dipole potential by phloretin, RH421, and 6-ketocholestanol as probed by gramicidin channel conductance
Duffin RL, et al.
Langmuir, 19(4), 1439-1442 (2003)
Samer Al-Samir et al.
Journal of enzyme inhibition and medicinal chemistry, 36(1), 1602-1606 (2021-07-16)
We have studied the CO2 permeability of the erythrocyte membrane of the rat using a mass spectrometric method that employs 18 O-labelled CO2. The method yields, in addition, the intraerythrocytic carbonic anhydrase activity and the membrane HCO3- permeability. For normal rat
Uptake of a fluorescent L-glucose derivative 2-NBDLG into three-dimensionally accumulating insulinoma cells in a phloretin-sensitive manner
Sasaki A, et al.
Human Cell : Official Journal of Human Cell Research Society, 29(1), 37-45 (2016)
Insulin-dependent, glucose transporter 1 mediated glucose uptake and tube formation in the human placental first trimester trophoblast cells
Basak S, et al.
Molecular and Cellular Biochemistry, 55(, pages=), 94-99 (2018)
Placental glucose transporter (GLUT)-1 is down-regulated in preeclampsia
Luscher BP, et al.
Placenta, 55(, pages=), 94-99 (2017)
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