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About This Item
Empirical Formula (Hill Notation):
C21H24O10 · 2H2O
CAS Number:
Molecular Weight:
472.44
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
200-487-1
MDL number:
Beilstein/REAXYS Number:
66621
Product Name
Phloridzin dihydrate, from apple wood, ≥99% (HPLC)
biological source
apple wood
Quality Level
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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signalword
Warning
hcodes
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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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)
