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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

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About This Item

Empirical Formula (Hill Notation):
C21H24O10 · 2H2O
CAS Number:
7061-54-3
Molecular Weight:
472.44
Beilstein:
66621
EC Number:
200-487-1
MDL number:
MFCD00149438
UNSPSC Code:
12352200
PubChem Substance ID:
24898413
NACRES:
NA.77

biological source

apple wood

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

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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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Phlorizin prevents glomerular hyperfiltration but not hypertrophy in diabetic rats
Malatiali S, et al.
Experimental Diabetes Research, 2008 (2008)
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)
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)
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