Phloridzin
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Phloridzin
structure -
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CAS No:
60-81-1
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Formula:
C21H24O10
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Chemical Name:
Phloridzin
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Synonyms:
1-Propanone,1-[2-(β-D-glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-;Phlorizin;1-[2-(β-D-Glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone;Phlorhizin;Phloridzin;Phlorizoside;Phlorrhizin;Phlorizine;Floridzin;Phloretin 2′-glucoside;Phloridzosid;NSC 2833;Phloretin 2′-O-glucoside;Phloretin 2′-O-β-D-glucopyranoside;Phloretin 2′-β-D-Glucoside;Dihydrochalcone 2′-β-D-glucopyranoside;Phloretin glucoside;112318-65-7;16055-86-0;52276-56-9
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CAS No:
Description
Phlorizin is a non-selective SGLT inhibitor with Kis of 300 and 39 nM for hSGLT1 and hSGLT2, respectively. Phlorizin is also a Na+/K+-ATPase inhibitor.
Solid
Phlorizin is an aryl beta-D-glucoside that is phloretin attached to a beta-D-glucopyranosyl residue at position 2' via a glycosidic linkage. It has a role as a plant metabolite and an antioxidant. It is an aryl beta-D-glucoside, a member of dihydrochalcones and a monosaccharide derivative. It derives from a phloretin.
Characteristics
177
1.2
Solid
1.452 g/cm3
110 °C
770°C at 760 mmHg
270.7±26.4 °C
1.686
1 mg/mL at 22 °C
2-8°C
194.4 Ų [M+Na]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
Safety Information
3
36/37/38
26-36
UC2080000
Xi
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 69 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Phloridzin Use and Manufacturing
Sodium-glucose cotransporter 1 (SGLT1) is a high affinity, low capacity transporter abundant in the small intestine, with some expression in the kidney as well. SGLT2 is a low affinity, high capacity transporter in the kidney that accounts for approximately 90% of glucose reabsorption into the blood stream. Selective inhibition of SGLT2 is a potential strategy for reducing plasma glucose levels as a treatment for diabetes. Phlorizin is a natural product, first isolated from the bark of apple trees, that reduces plasma glucose levels by blocking renal and intestinal glucose absorption through inhibition of SGLT1 and SGLT2. It competitively inhibits the initial rate of a-methyl-D-glucopyranoside (a-MDG) uptake in human COS-1 cells expressing hSGLT1 and hSGLT2 with IC50 values of 400 and 65 nM, respectively. In HEK293T cells expressing human SGLT1 and SGLT2, phlorizin exhibits Ki values of 140 and 11 nM, respectively, at 37°C.
Computed Properties
Molecular Weight:436.4
XLogP3:1.2
Hydrogen Bond Donor Count:7
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:7
Exact Mass:436.13694696
Monoisotopic Mass:436.13694696
Topological Polar Surface Area:177
Heavy Atom Count:31
Complexity:581
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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