Phloretin

Phloretin Basic information
Product Name:Phloretin
Synonyms:2,4,6-Trihydroxy-B-(4-Hydroxyphenyl)Propiophenone;Phloretin,98%;β-(4-hydroxyphenyl)-2,4,6-trihydroxypropiophenone;PHLORETIN(RG);1-Propanone, 3-(4-hydroxyphenyl)-1-(2,4,6-;trihydroxyphenyl)-;β-(4-Hydroxyphenyl)-2,4,6-trihydroxypropiophenone, 3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanone, 2μ,4μ,6μ-Trihydroxy-3-(4-hydroxyphenyl)propiophenone;2',4,4',6'-Tetrahydroxy-α,β-dihydro-trans-chalcone
CAS:60-82-2
MF:C15H14O5
MW:274.27
EINECS:200-488-7
Product Categories:chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;Chalcones;All Inhibitors;Inhibitors;Protein Kinase Inhibitors and Activators;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;standardized herbal extract;60-82-2
Mol File:60-82-2.mol
Phloretin Structure
Phloretin Chemical Properties
Melting point ~260 °C
Boiling point 337.26°C (rough estimate)
density 1.1827 (rough estimate)
FEMA 4390 | 3-(4-HYDROXYPHENYL)-1-(2,4,6-TRIHYDROXYPHENYL)PROPAN-1-ONE
refractive index 1.573-1.575
storage temp. 2-8°C
solubility Acetonitrile (Slightly), Methanol (Slightly)
pka7.16±0.40(Predicted)
form Powder
color White to beige
Odorodorless
Water Solubility soluble
Merck 14,7326
JECFA Number2022
BRN 1887240
InChIKeyVGEREEWJJVICBM-UHFFFAOYSA-N
LogP3.50
CAS DataBase Reference60-82-2(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 37/39-26-36
WGK Germany 3
3-10
HazardClass IRRITANT
HS Code 29145090
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
Phloretin Usage And Synthesis
Chemical PropertiesCrystalline Solid
Chemical PropertiesWhite to pale yellow solid.
UsesPhloretin 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

UsesAs glucose transport inhibitor, Phloretin can inhibits protein kinase C and has been shown to inhibit the entry of five enveloped viruses into human fibroblasts.
DefinitionChEBI: Phloretin is a member of the class of dihydrochalcones that is dihydrochalcone substituted by hydroxy groups at positions 4, 2', 4' and 6'. It has a role as a plant metabolite and an antineoplastic agent. It is functionally related to a dihydrochalcone.
General DescriptionPhloretin is a dihydrochalcone flavonoid with antioxidant activity usually found in apples and apple-derived products. It is extensively used for peroxynitrite scavenging and the inhibition of lipid peroxidation. It has been found to inhibit the growth of several cancer cells and induce apoptosis of B16 melanoma and HL60 human leukemia cells.
Biological Activityphloretin is a dihydrochalcone, a type of natural phenols which can be found in apple tree leaves and manchurian apricot. phloretin inhibits the active transport of glucose into cells via sodium-glucose linked transporter (sglt) 1 and 2 with ic50 value of 49±12 μm [2].sglts are a family of glucose transporter which is found in the small intestine mucosa (sglt 1) and nephron proximal tubule (sglt 2). they contribute to the renal glucose reabsorption.after treatment of phloretin, differentiated 3t3-l1 cells exhibited significantly enhanced glycerol and the inhibition of adipogenesis-related transcription factor that were regulated by sglts. additionally, phloretin promoted phosphorylation of amp-activated protein kinase and increased activity of adipose triglyceride lipase and hormone-sensitive lipase [1]. when raw 263.7 cells were cultured from differentiated 3t3-l1 cell media, pt suppressed the sglt-associated nuclear transcription factor kappab and mitogen-activated protein kinase pathways [1].in streptozotocin-induced rat model of diabetes type i, oral administration of phloridzin (5/10/20/40 mg/kg/day) resulted in significant reduction of blood glucose levels and improved dyslipidemia. additionally, administration of phloridzin reduced urine volume and water intake in a dose-dependent manner [3].
Biochem/physiol ActionsReacts with vic-dicarbonyl compounds such as glyoxal and methylglyoxal, preventing cytotoxic conjugation with biological macromolecules.
Purification MethodsCrystallise phloretin from aqueous EtOH. [Zemplen & Bognár Chem Ber 75 1040 1942, Zemplén Chem Ber 76 386 1943, Beilstein 8 IV 3518.]
references[1] huang w c et al. , phloretin and phlorizin promote lipolysis and inhibit inflammation in mouse 3t3-l1 cells and in macrophage-adipocyte co-cultures. mol nutr food res. 2013, 57: 1807-1817.
[2] kasahara t, kasahara m. expression of the rat glut1 glucose transporter in the yeast saccharomyces cerevisiae. biochem j. 1996, 315 ( pt 1):177-182.
[3] najafian m, jahromi m z, nowroznejhad m j, phloridzin reduces blood glucose levels and improves lipids metabolism in streptozotocin-induced diabetic rats. mol biol rep. 2012, 39(5): 5299-306.
Phloretin Preparation Products And Raw materials
Preparation ProductsUDP
TAXIFOLIN PHLORETIN-4,4'-DIMETHYLETHER(RG) Puerarin HOMOERIODICTYOL PHLORETIN-4-METHYL ETHER Di(trimethylol propane) PHLORETIN-4,4'-DIMETHYL ETHER PHLORETIN44DIETHYLETHER 5,7-DIHYDROXY-3',4',5'-TRIMETHOXYFLAVANONE Triacetonamine 6,8-DIMETHYL-4',5,7-TRIHYDROXYFLAVANONE HESPERETIN DIHYDROCHALCONE PHLORETIN2'GLUCOSIDE PHLORETIN-4,4'-DIMETHYLETHER(P) Phloretin 4'-glucoside 3'-Hydroxypropiophenone (+)-TAXIFOLIN ERIODICTYOL DIHYDROCHALCONE

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