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Phloretin

CAS No.60-82-2
Chemical Name:Phloretin
CBNumber:CB4161608
Molecular Formula:C15H14O5
Formula Weight:274.27
MOL File:60-82-2.mol

Phloretin Property

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)
pka 7.16±0.40(Predicted)
form Powder
color White to beige
Odor odorless
Water Solubility soluble
Merck 14,7326
JECFA Number 2022
BRN 1887240
InChIKey VGEREEWJJVICBM-UHFFFAOYSA-N
LogP 3.50
CAS DataBase Reference 60-82-2(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS) (TRIHYDROXY-PHENYL)-PROPAN-1-ONE
FDA UNII S5J5OE47MK
UNSPSC Code 85151701
NACRES NA.77

Safety

Hazard Codes :Xi
Risk Statements :36/37/38
Safety Statements :37/39-26-36
WGK Germany :3
F :3-10
HazardClass :IRRITANT
HS Code :29145090

NFPA 704:

	1
0		1

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H315-H319-H335
Precautionary statements P261-P264-P271-P280-P302+P352-P305+P351+P338

Phloretin Price More Price(16)

Brand: Sigma-Aldrich(India)
Product number: P7912
Product name : Phloretin
Purity: ≥99%
Packaging: 25MG
Price: ₹7772.35
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: P7912
Product name : Phloretin
Purity: ≥99%
Packaging: 100MG
Price: ₹12253.9
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: P7912
Product name : Phloretin
Purity: ≥99%
Packaging: 250MG
Price: ₹24670.18
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 91897
Product name : Phloretin
Purity: analytical standard
Packaging: 10MG
Price: ₹7750.7
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 524488
Product name : Phloretin - CAS 60-82-2 - Calbiochem
Purity: A cell-permeable inhibtor of protein kinase C (IC?? = 20-50 μM).
Packaging: 200MG
Price: ₹15469.99
Updated: 2022/06/14
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Phloretin Chemical Properties,Usage,Production

Chemical Properties Crystalline Solid
Chemical Properties White to pale yellow solid.
Uses 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
Uses As glucose transport inhibitor, Phloretin can inhibits protein kinase C and has been shown to inhibit the entry of five enveloped viruses into human fibroblasts.
Definition ChEBI: 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 Description Phloretin 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 Activity phloretin 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 Actions Reacts with vic-dicarbonyl compounds such as glyoxal and methylglyoxal, preventing cytotoxic conjugation with biological macromolecules.
Purification Methods Crystallise 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.