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P3449

Phloridzin dihydrate

From apple wood, ≥99% (HPLC), Na+-glucose cotransport inhibitor, powder

Synonym(s):

1-[2-(β-D-Glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone, Phloretin 2′-β-D-glucopyranoside, Phloretin 2′-β-D-glucoside, Phlorizin dihydrate

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About This Item

Empirical Formula (Hill Notation):
C21H24O10 · 2H2O
CAS Number:
7061-54-3
Molecular Weight:
472.44
NACRES:
NA.77
PubChem Substance ID:
24898413
UNSPSC Code:
12352200
EC Number:
200-487-1
MDL number:
MFCD00149438
Beilstein/REAXYS Number:
66621
Assay:
≥99% (HPLC)
Form:
powder
Quality level:
200
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Product Name

Phloridzin dihydrate, from apple wood, ≥99% (HPLC)

biological source

apple wood

Quality Level

200

assay

≥99% (HPLC)

form

powder

mp

113-114 °C (lit.)

SMILES string

O.O.OC[C@H]1O[C@@H](Oc2cc(O)cc(O)c2C(=O)CCc3ccc(O)cc3)[C@H](O)[C@@H](O)[C@@H]1O

InChI

1S/C21H24O10.2H2O/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;2*1H2/t16-,18-,19+,20-,21-;;/m1../s1

InChI key

XQWBNXSENPTIDY-YXMARJSJSA-N

Application

Phloridzin dihydrate has been used as:
  • a Na+-glucose cotransport inhibitor to test its effect in lowering blood glucose
  • a hexose carrier inhibitor to prevent glucose derivative 2-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-2-deoxyglucose (2-NBDG) uptake in sycamore cells
  • a non-specific sodium-glucose co-transporter 2 (SGLT2) inhibitor in embryonic cardiomyocyte cell line H9C2 to investigate its protective effect on Dox-induced cytotoxicity

Biochem/physiol Actions

Phloridzin is a glycoside present in the leaves and bark of apple. It is also present in peel and pulp of the apple fruit. Phloridzin belongs to the dihydrochalcones class of compounds. Lactase catabolizes phloridzin to phloretin and glucose in small intestine epithelial cells. Phloridzin is an antidiabetic agent and is equally bioavailable as phloretin.

Features and Benefits

Used to induce experimental glycosuria.

Other Notes

Dihydrochalcone glycoside found in apple tree

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pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SLCH3725
SLCF9285
SLBZ1564
SLBP3626V
SLBF2194V

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Articles

需氧糖酵解和瓦博格效应

本页面介绍了一篇有关瓦博格效应的文章，以及其如何能够在正常氧气水平下，增强肿瘤细胞中葡萄糖向乳酸的转化。Otto Heinrich Warburg在1924年证明，癌细胞显示出对糖酵解的依赖性增加，以满足他们的能量需求，无论是否有充足的氧气存在。

Aerobic Glycolysis and the Warburg Effect

Warburg effect enhances glucose to lactate conversion in tumor cells, regardless of oxygen levels; impacting cancer metabolism since 1924.

Phloridzin, an Apple Polyphenol, Exerted Unfavorable Effects on Bone and Muscle in an Experimental Model of Type 2 Diabetes in Rats
Londzin P, et al.
Nutrients, 10(11), 1701-1701 (2018)
Cardioprotective potential of an SGLT2 inhibitor against doxorubicin-induced heart failure
Oh CM, et al.
Korean circulation journal, 49 (2018)
Phlorizin prevents glomerular hyperfiltration but not hypertrophy in diabetic rats
Malatiali S, et al.
Experimental Diabetes Research, 2008 (2008)
View All Related Papers

Global Trade Item Number

SKUGTIN
P3449-100MG04061834367949
P3449-10G04061832575261
P3449-500MG04061834367956
P3449-5G04061834367963
P3449-1G04061826226308