Phlorizin

Modify Date: 2024-01-01 21:10:36

Phlorizin Structure
Phlorizin structure
 Common Name Phlorizin
CAS Number 60-81-1 Molecular Weight 436.409
Density 1.6±0.1 g/cm3 Boiling Point 770.0±60.0 °C at 760 mmHg
Molecular Formula C21H24O10 Melting Point 113-114 °C(lit.)
MSDS N/A Flash Point 270.7±26.4 °C

 Use of Phlorizin


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.

 Names

Name phlorizin
Synonym More Synonyms

 Phlorizin Biological Activity

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.
Related Catalog
Target

Ki: 300 nM (hSGLT1), 39 nM (hSGLT2)[1] Na+/K+-ATPase[2]

In Vitro Phlorizin is a non-selective SGLT inhibitor with Kis of 300 and 39 nM for hSGLT1 and hSGLT2, respectively[1]. Phlorizin is also a Na+/K+-ATPase inhibitor[2]. Phlorizin at 2×10-4 M inhibits Na+ and Rb+-activated ATPase activities in human red cell membranes by 43 %. At 1 mM and 7 mM RbCl, rubidium uptake is not changed or is slightly inhibited (less than 15 %) by 2×10-4 M Phlorizin[2]. Cell viability is not significantly altered by doses of Phlorizin <100 μM. Pretreating cells with Phlorizin does not significantly reduce nitrite or PGE2 levels. Phlorizin does not suppress IL-6 or TNF-α production, although 100 μM Phlorizin can significantly inhibit TNF-α expression[3].
In Vivo Prior to Phlorizin treatment, the blood glucose level in SDT fatty rats is 370±49 mg/dL. Six hours after dosing, the blood glucose level in the Phlorizin treated group decreases to an almost normal level (139±32 mg/dL). Phlorizin-treated SDT fatty rats are heavier than vehicle-treated SDT fatty rats after 12 weeks. Phlorizin treatment significantly decreases glucose excretion and delays insulin decreases. Creatinine clearance decreases significantly with Phlorizin treatment. 23 weeks of Phlorizin treatment prevents the decrease of nerve fibers (23.6±3.2 fibers/mm). Retinal abnormalities are completely prevented with Phlorizin[4].
Kinase Assay Resealed ghosts are obtained with the addition of 4×10-3 M ATP and 5×10-3 M MgCl2 with or without 5×10-4 M Phlorizin (final concentration) when red cells are hemolyzed. Ghosts corresponding to 0.4-0.45 mL of the original blood cells are incubated with 0.9 mL of Medium A and 86RbCl for 45 or 90 min and the radioactivity in 200 μL of the supernatant is determined. The ATPase activity in the resealed ghosts is determined from the increase in inorganic phosphate after incubation[1].
Cell Assay The RAW264.7 murine macrophage-derived cell line is used. Cell viability is measured using the 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Cells (105 cells/well) are cultured in 96-well plates and treated with varying concentrations of Phlorizin for 24 h. Next, the supernatant is removed and the cells are incubated with MTT (50 mg/mL) for 4 h at 37°C. The plates are washed and isopropanol is added to dissolve formazone crystals, then the absorbance values are measured at 570 nm using a microplate reader[3].
Animal Admin Female SDT fatty rats are used in this study. At six weeks of age, SDT fatty rats are divided into two groups (n=8); a Phlorizin treated group and a vehicle treated group. Age-matched female Sprague-Dawley (SD) rats are used as control animals (n=8). Animals are housed in a climate-controlled room (temperature 23±3°C, humidity 55±15%, 12 h lighting cycle) and allowed free access to basal diet and water. Phlorizin is injected subcutaneously once daily (100 mg/kg/day) to animals in the Phlorizin treated group for 23 weeks. Twenty % propylene glycol is administered to animals in the vehicle treated group and control SD rats[4].
References

[1]. Pajor AM, et al. Inhibitor binding in the human renal low- and high-affinity Na+/glucose cotransporters. J Pharmacol Exp Ther. 2008 Mar;324(3):985-91.

[2]. Nakagawa A, et al. Localization of the phlorizin site on Na, K-ATPase in red cell membranes. J Biochem. 1977 May;81(5):1511-5.

[3]. Chang WT, et al. Evaluation of the anti-inflammatory effects of phloretin and phlorizin in lipopolysaccharide-stimulated mouse macrophages. Food Chem. 2012 Sep 15;134(2):972-9.

[4]. Katsuda Y, et al. Contribution of hyperglycemia on diabetic complications in obese type 2 diabetic SDT fatty rats: effects of SGLT inhibitor phlorizin. Exp Anim. 2015;64(2):161-9.

 Chemical & Physical Properties

Density 1.6±0.1 g/cm3
Boiling Point 770.0±60.0 °C at 760 mmHg
Melting Point 113-114 °C(lit.)
Molecular Formula C21H24O10
Molecular Weight 436.409
Flash Point 270.7±26.4 °C
Exact Mass 436.136932
PSA 177.14000
LogP 0.45
Vapour Pressure 0.0±2.8 mmHg at 25°C
Index of Refraction 1.686
Storage condition 2-8°C

 MSDS

Section I.Chemical Product and Company Identification
Chemical Name Phlorizin
Portland OR
SynonymPhloridzin
Chemical FormulaC21H24O10•2H2O
CAS Number60-81-1
Section II.Composition and Information on Ingredients
Chemical NameCAS Number Percent (%)TLV/PELToxicology Data
Phlorizin60-81-1Min. 97.0 (T) Not available.Mouse LD (intraperitoneal)
>500mg/kg
Section III. Hazards Identification
Acute Health EffectsIrritating to eyes and skin on contact. Inhalation causes irritation of the lungs and respiratory system. Inflammation of the
eye is characterized by redness, watering, and itching. Skin inflammation is characterized by itching, scaling, reddening,
or, occasionally, blistering. Follow safe industrial hygiene practices and always wear proper protective equipment when
handling this compound.
Chronic Health EffectsCARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Reproductive: rat (intraperitoneal) 600mg/kg. Duration: female 8 days of pregnancy.
Effects on fertility- Post-implantation mortality.
There is no known effect from chronic exposure to this product. Repeated or prolonged exposure to this compound is
not known to aggravate existing medical conditions.
Section IV.First Aid Measures
Eye ContactCheck for and remove any contact lenses. IMMEDIATELY flush eyes with runing water for at least 15 minutes. keeping
eyelids open. COLD water may be used. DO NOT use an eye oitment. Flush eyes with running water for a minimum of
15 minutes, occasionally lifting the upper eyelids. Seek medical attention. Treat symptomatically and supportively.
Skin ContactAfter contact with skin, wash immediately with plenty of water. Gently and thorough wash the contaminated skin with
running water and non-abrasive soap. Be particularly careful to clean folds, crevices, creases and groin. COLD water
may be used. Cover the irritated skin with an emollient. Seek medical attention. Treat symptomatically and supportively.
Wash any contaminated clothing before reusing.
InhalationIf the victim is not breathing, perform artificial respiration. Loosen tight clothing such as a collar, tie, belt or waistband. If
breathing is difficult, oxygen can be administered. Seek medical attention. Treat symptomatically and supportively.
IngestionINDUCE VOMITING by sticking finger in throat. Lower the head so that the vomit will not reenter the mouth and throat.
Loosen tight clothing such as a collar, tie, belt, or waistband. If the victim is not breathing, administer artificial respiration.
Examine the lips and mouth to ascertain whether the tissues are damaged, a possible indication that the toxic material
was ingested; the absence of such signs, however, is not conclusive. Seek immediate medical attention and, if possible,
show the chemical label. Treat symptomatically and supportively.
Section V.Fire and Explosion Data
Auto-IgnitionNot available.
FlammabilityMay be combustible at high temperature.
Flash PointsFlammable LimitsNot available.
Not available.
Combustion Products
These products are toxic carbon oxides (CO, CO 2).
Fire Hazards
No specific information is available regarding the flammability of this compound in the presence of various materials.
Risks of explosion of the product in presence of mechanical impact: Not available.
Explosion Hazards
Risks of explosion of the product in presence of static discharge: Not available.
No additional information is available regarding the risks of explosion.
Fire Fighting Media
SMALL FIRE: Use DRY chemicals, CO 2, water spray or foam.
LARGE FIRE: Use water spray, fog or foam. DO NOT use water jet.
and Instructions
Continued on Next Page
Phlorizin
Section VI.Accidental Release Measures
Spill CleanupIrritating material.
InstructionsIn case of a spill and/or a leak, always shut off any sources of ignition, ventilate the area, and exercise caution. Use a
shovel to put the material into a convenient waste disposal container. Finish cleaning the spill by rinsing any
contaminated surfaces with copious amounts of water. Consult federal, state, and/or local authorities for assistance on
disposal.
Section VII. Handling and Storage
IRRITANT. Keep away from heat and sources of ignition. Mechanical exhaust required. When not in use, tightly seal the
Handling and Storage
container and store in a dry, cool place. Avoid excessive heat and light. DO NOT breathe dust.
Information
Always store away from incompatible compounds such as oxidizing agents.
Section VIII. Exposure Controls/Personal Protection
Engineering ControlsUse process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below
recommended exposure limits. If user operations generate dust, fume or mist, use ventilation to keep exposure to
airborne contaminants below the exposure limit.
Personal ProtectionSplash goggles. Lab coat. Dust respirator. Boots. Gloves. Be sure to use a MSHA/NIOSH approved respirator or
equivalent. Suggested protective clothing might not be sufficient; consult a specialist BEFORE handling this product.
Exposure LimitsNot available.
Section IX. Physical and Chemical Properties
Solubility
Physical state @ 20°CYellow powder.1g dissolves in water @ 22°C, 64mL water
@ 60°C, 22mL water @ 70°C.
Not available.Freely soluble in boiling water, in about 4
Specific Gravity
parts alcohol, methanol, amyl alcohol,
acetone, ethyl acetate, pyridine, aniline.
Practically insoluble in ether, chloroform
and benzene.
Molecular WeightPartition Coefficient
436.41 (Anh)Not available.
Boiling PointVapor Pressure
Not available.Not available.
Melting Point110°C (230°F)Vapor DensityNot available.
Refractive IndexNot available.VolatilityNot available.
Critical TemperatureNot available.OdorNot available.
ViscosityNot available.TasteSweet with biter aftertaste.
Section X.Stability and Reactivity Data
Stability
This material is stable if stored under proper conditions. (See Section VII for instructions)
Conditions of InstabilityAvoid excessive heat and light.
Incompatibilities
Reactive with strong oxidizing agents.
Section XI. Toxicological Information
RTECS NumberUC2080000
Eye contact. Ingestion. Inhalation. Skin contact.
Routes of Exposure
Toxicity DataMouse LD (intraperitoneal) >500mg/kg
Chronic Toxic EffectsCARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Reproductive: rat (intraperitoneal) 600mg/kg. Duration: female 8 days of pregnancy.
Effects on fertility- Post-implantation mortality.
There is no known effect from chronic exposure to this product. Repeated or prolonged exposure to this compound is not
known to aggravate existing medical conditions.
Acute Toxic EffectsIrritating to eyes and skin on contact. Inhalation causes irritation of the lungs and respiratory system. Inflammation of the
eye is characterized by redness, watering, and itching. Skin inflammation is characterized by itching, scaling, reddening,
or, occasionally, blistering. Follow safe industrial hygiene practices and always wear proper protective equipment when
handling this compound.
Continued on Next Page
Phlorizin
Section XII.Ecological Information
EcotoxicityNot available.
Not available.
Environmental Fate
Section XIII. Disposal Considerations
Recycle to process, if possible. Consult your local or regional authorities. You may be able to dissolve or mix material with
Waste Disposal
a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system. Observe all
federal, state, and local regulations when disposing of the substance.
Section XIV. Transport Information
DOT ClassificationNot a DOT controlled material (United States).
Not applicable.
PIN Number
Proper Shipping Name
Not applicable.
Packing Group (PG)Not applicable.
DOT Pictograms
Section XV. Other Regulatory Information and Pictograms
TSCA Chemical InventoryThis product is NOT on the EPA Toxic Substances Control Act (TSCA) inventory. The following notices are required by 40
CFR 720.36 (C) for those products not on the inventory list:
(EPA)
(i) These products are supplied solely for use in research and development by or under the supervision of a technically
qualified individual as defined in 40 CFR 720.0 et sec.
(ii) The health risks of these products have not been fully determined. Any information that is or becomes available will be
supplied on an MSDS sheet.
WHMIS ClassificationNot available.
(Canada)
EINECS Number (EEC) 200-487-1
EEC Risk StatementsR36/37/38- Irritating to eyes, respiratory system and skin.

SECTION 16 - ADDITIONAL INFORMATION
N/A

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UC2080000
CHEMICAL NAME :
1-Propanone, 1-(2-(beta-D-glucopyranosyloxy)-4,6-dihydroxyphenyl)- 3-(4-hydroxyphenyl)-
CAS REGISTRY NUMBER :
60-81-1
LAST UPDATED :
199512
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C21-H24-O10
MOLECULAR WEIGHT :
436.45
WISWESSER LINE NOTATION :
T6OTJ B1Q CQ DQ EQ FOR CQ EQ BV2R DQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CBCCT* "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. (National Academy of Science Library, 2101 Constitution Ave., NW, Washington, DC 20418) Volume(issue)/page/year: 6,226,1954 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
600 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
REFERENCE :
85DJA5 "Malformations Congenitales des Mammiferes," Tuchmann-Duplessis, H., Paris, Masson et Cie, 1971 Volume(issue)/page/year: -,95,1971

 Safety Information

Hazard Codes Xi: Irritant;
Risk Phrases R36/37/38
Safety Phrases S26-S36
WGK Germany 3
RTECS UC2080000

 Synthetic Route

Isosalipurposide structure

Isosalipurposide

CAS#:4547-85-7

~%

Phlorizin Structure

Phlorizin

CAS#:60-81-1

Literature: Chemische Berichte, , vol. 75, p. 1040,1041
(Ξ)-5-β-D-glucopyranosyloxy-7-hydroxy-2-(4-hydroxy-phenyl)-chroman-4-one structure

(Ξ)-5-β-D-gluco...

CAS#:23711-00-4

~%

Phlorizin Structure

Phlorizin

CAS#:60-81-1

Literature: Chemische Berichte, , vol. 76, p. 386,388,
4-hydroxybenzaldehyde structure

4-hydroxybenzal...

CAS#:123-08-0

~%

Phlorizin Structure

Phlorizin

CAS#:60-81-1

Literature: Chemische Berichte, , vol. 75, p. 1040,1041

 Synonyms

phlorizoside
4,6-dihydroxy-2-(β-D-glucosido)-β-(p-hydroxyphenyl)propiophenone
3,5-Dihydroxy-2-[3-(4-hydroxyphenyl)propanoyl]phenyl-β-D-glucopyranoside
1-(2,4-Dihydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}phenyl)-3-(4-hydroxyphenyl)-1-propanone
phloridzosid
phloridzine
Phlorrhizen
phloretin 2'-O-glucoside
1-Propanone, 1-[2-(β-D-glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-
Phlorizin
Isosalipurposide
Phloretin-2'-b-glucoside
Phloridzin
Phlorhizin
3,5-Dihydroxy-2-[3-(4-hydroxyphenyl)propanoyl]phenyl β-D-glucopyranoside
1-(2,4-Dihydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxyméthyl)tétrahydro-2H-pyran-2-yl]oxy}phényl)-3-(4-hydroxyphényl)-1-propanone
1-[2-(β-D-Glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone
1-(2,4-Dihydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}phenyl)-3-(4-hydroxyphenyl)-1-propanon
2'-(β-D-glucopyranosyloxy)-4',6'-dihydroxy-3-(4-hydroxyphenyl)propiophenone
4,6-Dihydroxy-2-(b-D-glucosido)-b-(p-hydroxyphenyl)propiophenone
Phloretin-2'-O-glucoside
Floridzin
MFCD00006591
1-[2-(b-D-Glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone
1-Propanone, 1-(2-(β-D-glucopyranosyloxy)-4,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)-
Phloretin-2'-β-glucoside
phlorrhizin
EINECS 200-487-1
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