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Merck
CN

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

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About This Item

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

Key Documents

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Product Name

Phloretin, ≥99%

InChI key

VGEREEWJJVICBM-UHFFFAOYSA-N

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

SMILES string

Oc1ccc(CCC(=O)c2c(O)cc(O)cc2O)cc1

assay

≥99%

form

powder

mp

~260 °C

storage temp.

2-8°C

Quality Level

200

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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.

General description

Major polyphenol found in apple; aglycone of phloridzin.
Phloretin a polar dye belongs to the class of dihydrochalcones.

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

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000523112
0000523115
0000523115
0000523112
0000456407

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Placental glucose transporter (GLUT)-1 is down-regulated in preeclampsia
Luscher BP, et al.
Placenta, 55(, pages=), 94-99 (2017)
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)
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)
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Articles

Aerobic Glycolysis and the Warburg Effect

Warburg effect enhances glucose to lactate conversion in tumor cells, regardless of oxygen levels; impacting cancer metabolism since 1924.

需氧糖酵解和瓦博格效应

本页面介绍了一篇有关瓦博格效应的文章，以及其如何能够在正常氧气水平下，增强肿瘤细胞中葡萄糖向乳酸的转化。Otto Heinrich Warburg在1924年证明，癌细胞显示出对糖酵解的依赖性增加，以满足他们的能量需求，无论是否有充足的氧气存在。

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