P7912

Sigma-Aldrich

Phloretin

≥99%

Synonym(s):
2′,4′,6′-Trihydroxy-3-(4-hydroxyphenyl)propiophenone, β-(4-Hydroxyphenyl)-2,4,6-trihydroxypropiophenone, 3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanone
Empirical Formula (Hill Notation):
C15H14O5
CAS Number:
Molecular Weight:
274.27
Beilstein/REAXYS Number:
1887240
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥99%

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

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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

Packaging

25, 100, 250 mg in poly bottle

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

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

hazcat

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

Target Organs

Respiratory system

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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)
Dan Cui et al.
ASN neuro, 12, 1759091420960550-1759091420960550 (2020-09-29)
In ischemic stroke, vasopressin hypersecretion is a critical factor of cerebral swelling and brain injury. To clarify neural mechanisms underlying ischemic stroke-evoked vasopressin hypersecretion, we observed the effect of unilateral permanent middle cerebral artery occlusion (MCAO) in rats on astrocytic...
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)
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)
Articles
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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