Phloretin

Names

[ CAS No. ]:
60-82-2

[ Name ]:
Phloretin

[Synonym ]:
QR CQ EQ BV2R DQ
1-Propanone, 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-
Dihydronaringenin
2',4',6',4-tetrahydroxydihydrochalcone
3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanone
β-(p-Hydroxyphenyl)phloropropiophenone
phloretol
4,2',4',6'-tetrahydroxydihydrochalcone
b-(p-Hydroxyphenyl)phloropropiophenone
UNII-S5J5OE47MK
3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
EINECS 200-488-7
Phloretin
MFCD00002288

Biological Activity

[Description]:

Phloretin(NSC 407292; RJC 02792) is a dihydrochalcone, a type of natural phenols. Phloretin inhibits the active transport of glucose into cells by SGLT1 and SGLT2.IC50 Value: 49 +/- 12 microM [4]Target: SGLT1/2in vitro: Phlorizin blocks glucose transport across the renal tubule at concentrations in renal blood and tissue in the range of 10-5 to 10-7 M [1]. PT significantly enhanced glycerol release and inhibited the adipogenesis-related transcription factors. PT also promoted phosphorylation of AMP-activated protein kinase and increased activity of adipose triglyceride lipase and hormone-sensitive lipase in 3T3-L1 cells [2]. Phloretin induced obvious cytotoxicity against BEL-7402 cells with IC50 of 89.23 microg/mL. The growth curve demonstrated decreased growth of the cells as phloretin concentration increased [3]. D-glucose-transport activity was observed with a Km for D-glucose of 3.4 +/- 0.2 mM (mean +/- S.E.M.) and was inhibited by cytochalasin B (IC50= 0.44 +/- 0.03 microM), HgCl2 (IC50)= 3.5 +/- 0.5 microM), phloretin (IC50= 49 +/- 12 microM) and phloridzin (IC50= 355 +/- 67 microM) [4].in vivo: The effect of phloridzin orally doses 5, 10, 20 and 40 mg/kg body weight on diabetes was tested in a streptozotocin-induced rat model of diabetes type 1. From beneficial effect of this compound is significant reduction of blood glucose levels and improve dyslipidemia in diabetic rats [5].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> SGLT

Research Areas >> Metabolic Disease

Natural Products >> Quinones

[References]

[1]. CHAN SS, LOTSPEICH WD. Comparative effects of phlorizin and phloretin on glucose transport in the cat kidney. Am J Physiol. 1962 Dec;203:975-9.

[2]. Huang WC, Chang WT, Wu SJ, Phloretin and phlorizin promote lipolysis and inhibit inflammation in mouse 3T3-L1 cells and in macrophage-adipocyte co-cultures. Mol Nutr Food Res. 2013 Jun 17.

[3]. Luo H, Wang YJ, Chen J, Phloretin induces apoptosis of BEL-7402 cells in vitro. Nan Fang Yi Ke Da Xue Xue Bao. 2008 Jul;28(7):1249-51.

[4]. Kasahara T, Kasahara M. Expression of the rat GLUT1 glucose transporter in the yeast Saccharomyces cerevisiae. Biochem J. 1996 Apr 1;315 ( Pt 1):177-82.

[5]. Najafian M, Jahromi MZ, Nowroznejhad MJ, Phloridzin reduces blood glucose levels and improves lipids metabolism in streptozotocin-induced diabetic rats. Mol Biol Rep. 2012 May;39(5):5299-306.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
534.4±29.0 °C at 760 mmHg

[ Melting Point ]:
~260 °C

[ Molecular Formula ]:
C₁₅H₁₄O₅

[ Molecular Weight ]:
274.269

[ Flash Point ]:
291.1±20.8 °C

[ Exact Mass ]:
274.084137

[ PSA ]:
97.99000

[ LogP ]:
3.50

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.685

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
soluble

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S37/39-S26

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2942000000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914501900

[ Summary ]:
2914501900 other ketone-phenols。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

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