P3449

Sigma-Aldrich

Phloridzin dihydrate

from apple wood, ≥99% (HPLC)

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
Empirical Formula (Hill Notation):
C21H24O10 · 2H2O
CAS Number:
Molecular Weight:
472.44
Beilstein/REAXYS Number:
66621
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

biological source

apple wood

assay

≥99% (HPLC)

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

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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

Packaging

100, 500 mg in poly bottle
1, 5, 10 g in poly bottle

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

hazcat

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

Target Organs

Respiratory system

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Phlorizin prevents glomerular hyperfiltration but not hypertrophy in diabetic rats
Malatiali S, et al.
Experimental Diabetes Research, 2008 (2008)
Cardioprotective potential of an SGLT2 inhibitor against doxorubicin-induced heart failure
Oh CM, et al.
Korean circulation journal, 49 (2018)
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)
Bioavailability of phloretin and phloridzin in rats.
Crespy V, et al.
The Journal of Nutrition, 131(12), 3227-3230 (2001)
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)
Articles
We presents an article about the Warburg effect, and how it is the enhanced conversion of glucose to lactate observed in tumor cells, even in the presence of normal levels of oxygen. Otto Heinrich Warburg demonstrated in 1924 that cancer cells show an increased dependence on glycolysis to meet their energy needs, regardless of whether they were well-oxygenated or not.
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