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: 2024-12-18 13:37:16
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) |
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| |
New Products
(S)-3-Aminobutanenitrile hydrochloride 4-Methylphenylacetic acid N-Boc-D-alaninol N-BOC-D/L-ALANINOL Tert-butyl bis(2-chloroethyl)carbamate 3-Morpholino-1-(4-nitrophenyl)-5,6-dihydropyridin- 2(1H)-one Furan-2,5-Dicarboxylic Acid Tropic acid 1-Bromo-3,5-Di-Tert-Butylbenzene S-2-CHLORO PROPIONIC ACID ETHYL ISOCYANOACETATE 2-Bromo-1,3-Bis(Dimethylamino)Trimethinium Hexafluorophosphate 4-IODO BENZOIC ACID 3-NITRO-2-METHYL ANILINE 1-(2,4-DICHLOROPHENYL) ETHANAMINE (2-Hydroxyphenyl)acetonitrile 4-Bromopyrazole 2-(Cyanocyclohexyl)acetic acid 4-methoxy-3,5-dinitropyridine 1-(4-(aminomethyl)benzyl)urea hydrochloride 2-aminopropyl benzoate hydrochloride diethyl 2-(2-((tertbutoxycarbonyl)amino) ethyl)malonate tert-butyl 4- (ureidomethyl)benzylcarbamate Ethyl-2-chloro((4-methoxyphenyl)hydrazono)acetateRelated products of tetrahydrofuran
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