| Identification | More | [Name]
Phloretin | [CAS]
60-82-2 | [Synonyms]
2',4',6',4-TETRAHYDROXYDIHYDROCHALCONE
2',4',6'-TRIHYDROXY-3-(4-HYDROXYPHENYL)-1-PROPIOPHENONE
2',4',6'-TRIHYDROXY-3-(4-HYDROXYPHENYL)-PROPIOPHENONE
2',4',6'-TRIHYDROXY-3-P-HYDROXYPHENYLPROPIOPHENONE
2,4,6-TRIHYDROXY-BETA-(4-HYDROXYPHENYL)PROPIOPHENONE
3-[4-HYDROXYPHENYL]-1-[2,4,6-TRIHYDROXYPHENYL]-1-PROPANONE
4,2',4',6'-TETRAHYDROXYDIHYDROCHALCONE
BETA-(4-HYDROXYPHENYL)-2,4,6-TRIHYDROXY-PROPIOPHENONE
PHLORETIN
PHLORETIN (NATURAL)
3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
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-
Dihydronaringenin
Floretin
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 | [EINECS(EC#)]
200-488-7 | [Molecular Formula]
C15H14O5 | [MDL Number]
MFCD00002288 | [Molecular Weight]
274.27 | [MOL File]
60-82-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystalline Solid | [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) | [form ]
Powder | [pka]
7.16±0.40(Predicted) | [color ]
White to beige | [Odor]
odorless | [Water Solubility ]
soluble | [Usage]
A glucose transport inhibitor. Also inhibits protein kinase C and has been shown to inhibit the entry of five enveloped viruses into human fibroblasts | [Detection Methods]
HPLC | [JECFA Number]
2022 | [Merck ]
14,7326 | [BRN ]
1887240 | [InChIKey]
VGEREEWJJVICBM-UHFFFAOYSA-N | [LogP]
3.50 | [CAS DataBase Reference]
60-82-2(CAS DataBase Reference) | [Storage Precautions]
Light sensitive;Store under nitrogen |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [F ]
3-10 | [HazardClass ]
IRRITANT | [HS Code ]
29145090 |
| Hazard Information | Back Directory | [Chemical Properties]
Crystalline Solid | [Chemical Properties]
White to pale yellow solid.
| [Uses]
A calcium channel protein inhibitor. | [Uses]
antidiabetic, inhibits glucose transport | [Uses]
antioxidant cosmetic use | [Uses]
The aglucon of Phlorizin. A glucose transport inhibitor. Also inhibits protein kinase C and has been shown to inhibit the entry of five enveloped viruses into human fibroblasts. | [Definition]
ChEBI: A member of the class of dihydrochalcones that is dihydrochalcone substituted by hydroxy groups at positions 4, 2', 4' and 6'. | [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. | [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. |
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