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60-81-1 (Phlorizin)

1

Identification

Phlorizin Phlorizin
Name Phlorizin
Formula C21H24O10
MW 436.41
CAS No. 60-81-1
EINECS 200-487-1
Smiles O=C(CCC1=CC=C(O)C=C1)C(C(O)=CC(O)=C2)=C2O[[email protected]@H]3O[[email protected]](CO)[[email protected]@H](O)[[email protected]](O)[[email protected]]3O
Synonyms 1-(2-(beta-D-Glucopyranosyloxy)-4,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)-propan-1-on; 1-(2,4-dihydroxy-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-3-(4-hydroxyphenyl)propan-1-one
InChI InChI=1S/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-15-8-12(24)7-14(26)17(15)13(25)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-24,26-29H,3,6,9H2/t16-,18-,19+,20-,21-/m1/s1
2

Introduction

Phlorizin, a natural product and dietary constituent found in a number of fruit trees, is a 2'-glucoside of phloretin, Phlorizin is a competitive and classic inhibitor of hSGLT1(Ki=300 nM) and hSGLT2(Ki= 39 uM).

Background Information

Phlorizin is a dihydrochalcone found in all parts of the apple tree except the mature fruit. Once thought to occur in other Rosaceae such as pear, plum and cherry trees. Inhibitor of Na+-glucose cotransporters (SGLT). Produces renal glycosuria and blocks intestinal glucose absorption. Normalizes insulin sensitivity in diabetic rats. ......by Affix Scientific
Phlorizin, a natural product and dietary constituent found in a number of fruit trees, is a 2'-glucoside of phloretin, Phlorizin is a competitive and classic inhibitor of hSGLT1(Ki=300 nM) and hSGLT2(Ki= 39 uM). IC50 value: 300 nM (Ki, SGLT1); 39 nM (Ki, SGLT2) [1] Target: SGLT1; SGLT2 in vitro: Inhibition by phlorizin was competitive, with K(i) values of 0.3 muM in hSGLT1 and 39 nM in hSGLT2 [1]. Phlorizin was unable to exchange with dapagliflozin bound to hSGLT2. In contrast, dapagliflozin, fluoro-dapagliflozin, and galacto-dapagliflozin dissociated quickly from hSGLT1 (t(1/2,Off) = 1-2 s), and phlorizin readily exchanged with dapagliflozin bound to hSGLT1 [2]. in vivo: A PK-PD model was developed next to analyze the inhibitory effect of phlorizin on renal glucose reabsorption. The model suitably expressed the concentration-dependent inhibitory effect of phlorizin on renal glucose reabsorption. The in vivo inhibition constants of phlorizin for SGLT in rats were estimated to be 67 nM for SGLT1 and 252 nM for SGLT2, which are similar to the in vitro data reported previously [3]. Phlorizin significantly decreased body weight gain and the levels of serum fasting blood glucose (FBG), triglycerides (TG), total cholesterol (TC), and advanced glycation end products (AGEs). Morphologic observations showed that normal myocardial structure was better preserved after phlorizin treatment [4]. ......by MedChemexpress Co., Ltd.
Phlorizin is a dihydrochalcone found in the bark of pear (Pyrus communis), apple, cherry and other fruit trees. ......by Selleck Chemicals LLC
Features and Benefits Used to induce experimental glycosuria. Other Notes Dihydrochalcone glycoside found in apple tree ......by Target Molecule Corp.
Inhibitor of Na<sup>+</sup>-glucose cotransporters (SGLT). Produces renal glycosuria and blocks intestinal glucose absorption. Normalizes insulin sensitivity in diabetic rats. ......by Tocris Bioscience Inc.
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Protocol(Only for Reference)

Cell Experiment

Animal Experiment

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Physical and Chemical Properties

Appearance:White to off-white Solid EBNumber:EB000015342

Storage condition

Up to one week at 4°C or six months at -20°C. by Affix Scientific
Store at -20&deg;C by Tocris Bioscience Inc.

Solubility

DMSO 87 mg/ml; Water <1 mg/ml by MedChemexpress Co., Ltd.
(25°C) * In vitro DMSO 87 mg/mL warming (199.35 mM); Ethanol9 mg/mL warming (20.62 mM); Water<1 mg/mL (<1 mM) by Selleck Chemicals LLC
Soluble to 100 mM in DMSO and to 100 mM in ethanol by Tocris Bioscience Inc.
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Mechanism and Indication

Signaling Pathways Membrane Transporter/Ion Channel
Target SGLT
Research Area Metabolic Disease
Indications
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Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
Phlorizin - Not Found
Phlorizin - No Development Reported
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Safety Data of Phlorizin

Hazard Symbols : Xi
Risk Statements : 36/37/38
Safety Statements : 26-36
RTECS : UC2080000
WGKGermany : 3
8

Spectral Information

9

Suppliers List

Company Price and Availability Country/Region
Affix Scientific 5g/USD400(In stock);10g/USD550(In stock) USA
Aktin Chemicals Inc China
Ankang Zhongke Maidisen Natural Pharmaceutical Co., Ltd. China
BioBioPha Co., Ltd. China
CHEMSCENE, LLC USA
Chengdu Biopurify Phytochemicals Ltd. China
Fraken Biochem Co., Ltd. China
Hangzhou Skyherb Technologies Co., Ltd. China
Indofine Chemical Company, Inc. USA
Ivy Fine Chemicals USA
MedChemexpress Co., Ltd. 1g/USD50(In stock);5g/USD190(In stock) USA
Nanning Weikang Pharmaceutical Technology Co., Ltd. China
Selleck Chemicals LLC 500mg/USD40(In stock);10mM/1mLIn DMSO/USD50(In stock) USA
Shaanxi Green Bio-Engineering Co., Ltd. China
Shanghai Haoyuan Chemexpress Co., Ltd. 1g/USD40(Get quote);5g/USD120(Get quote) China
Sino-Future Bio-Tech Co., Ltd. China
Target Molecule Corp. 20mg/USD23();50mg/USD45();250mg/USD110();500mg/USD168() USA
Tocris Bioscience Inc. USA
Wilshire Technologies USA
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Related Products

Other Forms of 60-81-1

Name CAS No Formula MW
Phlorizin dihydrate 7061-54-3 C21H28O12 472.44

Recommended Compounds in SGLT

Name CAS No Formula MW
Dapagliflozin ((2S)-1,2-propanediol, hydrate) 960404-48-2 C24H35ClO9 502.98
Canagliflozin (hemihydrate) 928672-86-0 C24H25FO5S 444.52
Phloretin 60-82-2 C15H14O5 274.27
LX-4211 1018899-04-1 C21H25ClO5S 424.94
TOFOGLIFLOZIN 1201913-82-7 C22H28O7 404.45
PF-04971729 1210344-57-2 C22H25ClO7 436.88
Empagliflozin 864070-44-0 C23H27ClO7 450.91
CSG 452 903565-83-3 C22H26O6 386.44
Ipragliflozin 761423-87-4 C21H21FO5S 404.45
Dapagliflozin 461432-26-8 C21H25ClO6 408.87
Canagliflozin 842133-18-0 C24H25FO5S 444.52
Bexagliflozin 1118567-05-7 C24H29ClO7 464.94

Recommended Compounds in Same Indication

Name CAS No Formula MW
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Route of Synthesis

12

References

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More Information

Phlorizin

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