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HomeProduct name listPhlorizin

Phlorizin

Synonym(s):Phlorizin;Phlorizin dihydrate;1-[2-(β-D-Glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone;Floridzin;Phloretin 2′-β-D-glucopyranoside

  • CAS NO.:60-81-1
  • Empirical Formula: C21H24O10
  • Molecular Weight: 436.41
  • MDL number: MFCD00006591
  • EINECS: 200-487-1
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 23:02:33
Phlorizin Structural

What is Phlorizin?

Chemical properties

Light Yellow Powder

The Uses of Phlorizin

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.

The Uses of Phlorizin

It is a dihydrochalcone occurring in all parts of the apple tree except the mature fruit. Once thought to occur in pear, plum, cherry trees and other Rosaceae

The Uses of Phlorizin

induces experimental glucosuria, antifeedant

What are the applications of Application

Phloridzin is an SGLT-1 and SGLT-2 inhibitor found in apple trees

Definition

ChEBI: An aryl beta-D-glucoside that is phloretin attached to a beta-D-glucopyranosyl residue at position 2' via a glycosidic linkage.

Purification Methods

-D-glucoside] [60-81-1] M 472.5, m 110o, [] 20 -62o (c 3.2, EtOH). Phlorizin crystallises as the dihydrate from water and causes glycosuria. [Brazy & Dennis Am J Physiol 234 1279 1978, Zemplen & Bognár Chem Ber 17B 1040 1943, Beilstein 17/7 V 177.]

Properties of Phlorizin

Melting point: 113-114 °C(lit.)
Boiling point: 468.89°C (rough estimate)
Density  1.3178 (rough estimate)
refractive index  -54 ° (C=3.2, 95% EtOH)
storage temp.  Keep in dark place,Sealed in dry,Room Temperature
solubility  DMSO (Slightly), Methanol (Slightly)
form  Solid
pka 7.15±0.40(Predicted)
color  Light Yellow to Tan
Merck  14,7327
CAS DataBase Reference 60-81-1(CAS DataBase Reference)
EPA Substance Registry System Phlorizin (60-81-1)

Safety information for Phlorizin

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Phlorizin

InChIKey IOUVKUPGCMBWBT-LKLLPNDVNA-N
SMILES C(C1C(=CC(O)=CC=1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O)(=O)CCC1C=CC(O)=CC=1 |&1:9,10,11,13,15,r|

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