Phloretin

Modify Date: 2024-01-02 21:00:36

Phloretin Structure
Phloretin structure
 Common Name Phloretin
CAS Number 60-82-2 Molecular Weight 274.269
Density 1.4±0.1 g/cm3 Boiling Point 534.4±29.0 °C at 760 mmHg
Molecular Formula C15H14O5 Melting Point ~260 °C
MSDS Chinese USA Flash Point 291.1±20.8 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Phloretin


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].

 Names

Name phloretin
Synonym More Synonyms

 Phloretin 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
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.

 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

 Safety Information

Symbol GHS07
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

 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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 Synonyms

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
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Related Compounds: More...
phloretin triacetate
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phloretin-4-D-glucoside
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phloretin 2'-O-glucoside
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PHLORETIN-4-METHYL ETHER
76172-68-4
PHLORETIN-4-METHYL ETHER
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Phloretin 4'-methyl ether
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Phloretin 2'-O-rhamnoside
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PHLORETIN-4,4'-DIMETHYL ETHER
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Phloretin 3',5'-Di-C-glucoside
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1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
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2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
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1226442-78-9
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(4-Methyl-tetrahydro-furan-2-yl)-methanol
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N-(1-cyanocyclopentyl)-2-[4-(4-fluorobenzenesulfonyl)-1,4-diazepan-1-yl]acetamide
930439-75-1
N-(2-(4-(dimethylamino)phenyl)-2-morpholinoethyl)-5,6,7,8-tetrahydronaphthalene-2-sulfonamide
946316-75-2
4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carbaldehyde
1018584-77-4
tert-Butyl-DL-alanine
1375289-11-4
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