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Merck

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

Key Documents

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Product Name

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

InChI key

XQWBNXSENPTIDY-YXMARJSJSA-N

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

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

biological source

apple wood

assay

≥99% (HPLC)

form

powder

mp

113-114 °C (lit.)

Quality Level

200

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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

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
0000504166
0000504152
0000504170
0000504170
0000504152

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Existence of two parallel mechanisms for glucose uptake in heterotrophic plant cells
Etxeberria Ed, et al.
Journal of Experimental Botany, 56(417), 1905-1912 (2005)
Cardioprotective potential of an SGLT2 inhibitor against doxorubicin-induced heart failure
Oh CM, et al.
Korean circulation journal, 49 (2018)
Cells sorted off hiPSC-derived kidney organoids coupled with immortalized cells reliably model the proximal tubule.
Banan Sadeghian, et al.
Communications biology, 6, 483-483 (2023)
Fernando F Anhê et al.
Gut (2022-08-26)
Bariatric surgery is an effective treatment for type 2 diabetes (T2D) that changes gut microbial composition. We determined whether the gut microbiota in humans after restrictive or malabsorptive bariatric surgery was sufficient to lower blood glucose. Women with obesity and
Phlorizin prevents glomerular hyperfiltration but not hypertrophy in diabetic rats
Malatiali S, et al.
Experimental Diabetes Research, 2008 (2008)
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