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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
Assay:
≥99%
Form:
powder
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Product Name

Phloretin, ≥99%

Quality Segment

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

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

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.
Blocks L-type Ca2+ channels; activates Ca2+-activated K+ channels in amphibian myelinated nerve fibers. Monocarboxylate transporter inhibitor.
Reacts with vic-dicarbonyl compounds such as glyoxal and methylglyoxal, preventing cytotoxic conjugation with biological macromolecules.

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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Codes

H315,H319,H335

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 (personal protective equipment)

Eyeshields, Gloves, type N95 (US)

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