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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:
Poids moléculaire :
274.27
Beilstein:
1887240
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352202
ID de substance PubChem :
Nomenclature NACRES :
NA.77
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Nom du produit

Phloretin, ≥99%

Niveau de qualité

Essai

≥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

Major polyphenol found in apple; aglycone of phloridzin.
Phloretin a polar dye belongs to the class of dihydrochalcones.[1]

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[2]
  • to incubate microvesicles in order to inhibit GLUT1 (glucose transporter 1)-mediated transport in radioactive ligand up-take assay[3]
  • as a component of KRH buffer to stop glucose uptake by trophoblast cells in vitro[4]

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.[5] Phloretin possess antitumor action by preventing protein kinase C (PKC) activity and stimulating programmed cell death.[6] It is found to inhibit the transport functions of GLUTs (glucose transporter) and aquaporins.[2]
Reacts with vic-dicarbonyl compounds such as glyoxal and methylglyoxal, preventing cytotoxic conjugation with biological macromolecules.

Pictogrammes

Exclamation mark

Mention d'avertissement

Warning

Mentions de danger

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)


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Consulter la Bibliothèque de documents

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

Articles

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

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

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

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

Questions

1–2 of 2 Questions  
  1. この製品の溶解方法と溶解した後の保存方法と、保存可能期間をどうか教えてください。 Please let me know how to dissolve this product, how to store it, and how long it can be stored after dissolving.

    1 answer
    1. This product is tested for solubility in methanol at 50 mg/mL and is also soluble in ethanol and DMSO. The stability in solution has not been determined. However, an identical product, 524488, notes that solutions are stable when stored in aliquots at -20°C for up to 1 month.

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  2. What is the solubility of Phloretin in DMSO?

    1 answer
    1. Stock solutions of phloretin can be prepared in DMSO at 100 mM

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