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Merck
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Key Documents

P7912

Sigma-Aldrich

Phloretin

≥99% (HPLC), powder, GLUT inhibitor

Sinônimo(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

Fórmula empírica (Notação de Hill):
C15H14O5
Número CAS:
Peso molecular:
274.27
Beilstein:
1887240
Número CE:
Número MDL:
Código UNSPSC:
12352202
ID de substância PubChem:
NACRES:
NA.77

product name

Phloretin, ≥99%

Nível de qualidade

Ensaio

≥99%

forma

powder

pf

~260 °C

temperatura de armazenamento

2-8°C

cadeia de caracteres 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

chave InChI

VGEREEWJJVICBM-UHFFFAOYSA-N

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Descrição geral

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

Aplicação

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

Ações bioquímicas/fisiológicas

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.

Pictogramas

Exclamation mark

Palavra indicadora

Warning

Frases de perigo

Classificações de perigo

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

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 2

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)


Certificados de análise (COA)

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Os clientes também visualizaram

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)

Artigos

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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