60-82-2

Basic information

• Product Name: Phloretin
• Synonyms: Phloretin Synonyms 2',4',6'-Trihydroxy-3-(4-hydroxyphenyl)propiophenone;1-Propanone, 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-;Phloretin 2',4',6'-Trihydroxy-3-(4-hydroxyphenyl)propiophenone;METHYL-4-4-(4-HYDROXYDIPHENYL METHYL)-PIPERIDINE-1-OXOBUTYL-2,2-DIMETHYLPHENYL ACETIC ACID.FEXOFENADINE INTERMEDIATE;PHLORETIN;PHLORETIN (NATURAL);4,2',4',6'-TETRAHYDROXYDIHYDROCHALCONE;3-[4-HYDROXYPHENYL]-1-[2,4,6-TRIHYDROXYPHENYL]-1-PROPANONE
• CAS NO: 60-82-2
• Molecular Formula: C₁₅H₁₄O₅
• Molecular Weight: 274.27
• EINECS: 200-488-7
• Product Categories: standardized herbal extract;Chalcones;All Inhibitors;Inhibitors;Protein Kinase Inhibitors and Activators;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).
• Mol File: 60-82-2.mol

Chemical Properties

• Melting Point: ~260 °C
• Boiling Point: 337.26°C (rough estimate)
• Flash Point: 291.1 °C
• Appearance: White to beige/Powder
• Density: 1.1827 (rough estimate)
• Vapor Pressure: 1.4E-05mmHg at 25°C
• Refractive Index: 1.573-1.575
• Storage Temp.: 2-8°C
• Solubility: Acetonitrile (Slightly), Methanol (Slightly)
• PKA: 7.16±0.40(Predicted)
• Water Solubility: soluble
• Merck: 14,7326
• BRN: 1887240
• CAS DataBase Reference: Phloretin(CAS DataBase Reference)
• NIST Chemistry Reference: Phloretin(60-82-2)
• EPA Substance Registry System: Phloretin(60-82-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36
• WGK Germany: 3
• F: 3-10
• HazardClass: IRRITANT
• Hazardous Substances Data: 60-82-2(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 60-82-2 differently. You can refer to the following data:
1. Crystalline Solid
2. White to pale yellow solid.

Uses

Different sources of media describe the Uses of 60-82-2 differently. You can refer to the following data:
1. 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) uptaketo incubate microvesicles in order to inhibit GLUT1 (glucose transporter 1)-mediated transport in radioactive ligand up-take assayas a component of KRH buffer to stop glucose uptake by trophoblast cells in vitro
2. 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 signi?cant 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.

InChI:InChI=1/C9H10O4/c1-5(10)9-7(11)3-6(13-2)4-8(9)12/h3-4,11-12H,1-2H3

Upstream product

• 108-73-6 3,5-dihydroxyphenol 
• 17362-17-3 3-(p-hydroxyphenyl)propiononitrile 
• 950186-11-5 3-(4-acetoxyphenyl)propanenitrile 
• 4192-90-9 4'-(β-D-glucopyranosyloxy)-2',4”,6'-trihydroxydihydrochalcone 
• 18916-17-1 [4-[[2-O-(6-deoxy-L-mannopyranosyl)-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone 
• 25324-31-6 phloretin-2',4'-di-O-β-D-glucopyranoside 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 88607-79-8 (E)-1-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-3-(4-(benzyloxy)phenyl)prop-2-en-1-one 
• 25515-46-2 2',4',6',4-tetrahydroxydihydrochalcone 
• 501-97-3 4-hydroxyphenylpropionic acid 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 
• 22867-43-2 (2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}prop-2-enoic acid 
• 53563-09-0 3-(4-nitrophenyl)propanenitrile 

Downstream Products

• 3791-75-1 2'-hydroxy-4,4',6'-trimethoxydihydrochalcone 
• 108-73-6 3,5-dihydroxyphenol 
• 501-97-3 4-hydroxyphenylpropionic acid 
• 99-96-7 4-hydroxy-benzoic acid 
• 42385-89-7 acetic acid 4-[3-oxo-3-(2,4,6-triacetoxy-phenyl)propyl]phenyl ester 
• 10210-17-0 3-(4-hydroxyphenyl)propan-1-ol 
• 108-46-3 recorcinol 
• 101467-70-3 5,7-dihydroxy-3-[(4-hydroxyphenyl)methyl]-4H-chromen-4-one 
• 160255-00-5 3',5'-dibromophloretin 
• 1005139-34-3 1-(4-hydroxy-2,6-bis-nitrooxy-phenyl)-3-(4-nitrooxy-phenyl)-propan-1-one 
• 157405-84-0 3-bromo-phloretin 
• 107585-77-3 5,7-dihydroxy-3-(4′-hydroxybenzyl)chroman-4-one 
• 200878-68-8 C₁₅H₁₃ClO₅ 
• 1133352-99-4 C₂₉H₃₂O₁₄ 

Relevant articles and documents

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The invention discloses a class of quinoid dihydrochalcone C-glycoside compounds with glucose on a ring A, a preparation method and anti-cerebral ischemia injury activity thereof, wherein the compoundhas a structure represented by a general formula (I). The preparation method of the compound comprises the following steps: (1) synthesizing a 2,4,6-trihydroxy dihydrochalcone compound; (2) synthesizing a 2,4,6-trihydroxy-3,5-diglucosyl dihydrochalcone C-glycoside compound; and (6) synthesizing a class of quinoid dihydrochalcone C-glycoside compound with glucose in the A ring. The compound disclosed by the invention is simple in preparation method and has a remarkable effect of resisting cerebral ischemia injury.

Novel compound from plasma-treated phloridzin and anti-obesity composition comprising the same as effective component

The present invention relates to a novel compound derived from plasma-treated phloridzin and an anti-obesity composition comprising the same as an effective component and, more specifically, to a diameric compound derived from phloridzin, which is newly formed by plasma-treating phloridzin (methylene-bis-phloridzin, diglucosyl-methylene-bis-phloridzin, and methylene-bis-phloretin), and to an anti-obesity composition comprising the same as an effective component. In particular, the compound derived from phloridzin, comapred to phloridzin, inhibits the activity of pancreatic lipase and enhances the effect of suppressing fat accumulation during differentiation of fat cells. In particular, the methylene-bis-phloretin of the present invention, a diameric body formed by phloretin using a methyl group, a form of which sugars are removed from phloridzin, has excellent inhibitory effect on fat accumlation as compared to phloretin, and thus may be beneficially used as a material for anti-obesity therapeutic agents or anti-obesity functional health foods.COPYRIGHT KIPO 2019

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