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P7912

Sigma-Aldrich

Phloretin

≥99% (HPLC), powder, GLUT inhibitor

Synonyme(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

Formule empirique (notation de Hill):
C15H14O5
Numéro CAS:
60-82-2
Poids moléculaire :
274.27
Numéro Beilstein :
1887240
Numéro CE :
200-488-7
Numéro MDL:
MFCD00002288
Code UNSPSC :
12352202
ID de substance PubChem :
24278652
Nomenclature NACRES :
NA.77

product name

Phloretin, ≥99%

Niveau de qualité

200

Pureté

≥99%

Forme

powder

Pf

~260 °C

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

VGEREEWJJVICBM-UHFFFAOYSA-N

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Description générale

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

Actions biochimiques/physiologiques

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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)
Anti-apoptotic effect of phloretin on cisplatin-induced apoptosis in HEI-OC1 auditory cells
Choi BM, et al.
Pharmacological Reports, 63(3), 708-716 (2011)
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)
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)
Afficher tous les articles scientifiques apparentés

Articles

Aerobic Glycolysis and the Warburg Effect

We presents an article about the Warburg effect, and how it is the enhanced conversion of glucose to lactate observed in tumor cells, even in the presence of normal levels of oxygen. Otto Heinrich Warburg demonstrated in 1924 that cancer cells show an increased dependence on glycolysis to meet their energy needs, regardless of whether they were well-oxygenated or not.

Aerobic Glycolysis and the Warburg Effect

We presents an article about the Warburg effect, and how it is the enhanced conversion of glucose to lactate observed in tumor cells, even in the presence of normal levels of oxygen. Otto Heinrich Warburg demonstrated in 1924 that cancer cells show an increased dependence on glycolysis to meet their energy needs, regardless of whether they were well-oxygenated or not.

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