Phlorizin

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Structural formula
Structure of the phlorizin
General
Surname Phlorizin
other names
  • Phloridzin
  • Phlorrhizine
  • 2 ′ - (β- D- glucopyranosyloxy) -4 ′, 6′-dihydroxy-3- (4-hydroxyphenyl) -propiophenone
  • PHLORIDZIN ( INCI )
Molecular formula C 21 H 24 O 10
Brief description

white, odorless solid

External identifiers / databases
CAS number
  • 60-81-1
  • 7061-54-3 (dihydrate)
EC number 200-487-1
ECHA InfoCard 100,000,443
PubChem 6072
ChemSpider 16498836
Wikidata Q413105
properties
Molar mass 436.4 g mol −1
Physical state

firmly

Melting point

106-109 ° C

boiling point

decomposition

solubility

poor in water (1 g l −1 at 22 ° C)

safety instructions
GHS labeling of hazardous substances

Dihydrate

07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
Toxicological data

> 500 mg kg −1 ( LD 50 ,  mouse ,  ip )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Phlorizin (also phloridzin , phlorrhizin ) is a vegetable glycoside from the group of flavonoids ( chalcones ), which is formally derived from phloroglucin .

Phloretin, the aglycon of phlorizin.
Bark of a cherry tree

Phlorizin is found in the bark of pears ( Pyrus communis ), apples , cherries and other fruit trees ( Rosaceae ). The aglycon of the substance is phloretin .

properties

The crystalline, white to yellowish, sweet-tasting substance contains four molecules of crystal water and melts at 106-109 ° C. From around 200 ° C it decomposes to rufin. It dissolves poorly in cold water and ether , better in hot water and ethanol . With prolonged exposure to aqueous acid solutions , phlorizin hydrolyzes to phloretin and glucose.

Effect and use

Phlorizin and phloretin block specifically the glucose - absorption by the renal tubules by inhibition of the sodium / glucose cotransporter SGLT1 what a glucosuria ( Phlorizindiabetes causes). Phlorizin was previously used as a substitute for quinine and in experimental physiology.

Individual evidence

  1. ↑ entry to phloridzin in CosIng database of the European Commission, accessed on 7 April 2020th
  2. ↑ Phlorizin data sheet (PDF) from Carl Roth , accessed on March 9, 2010.
  3. ↑ a b Ch. Gerhardt (Ed.): Textbook of Organic Chemistry , 1857, Wigand-Verlag.
  4. ↑ a b Entry on phlorizin in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  5. ↑ a b data sheet phloridzin dihydrate from Sigma-Aldrich , accessed on April 19, 2011 ( PDF ).
  6. ↑ Summary Tables of Biological Tests. National Research Council Chemical-Biological Coordination Center. Vol. 6, p. 226, 1954.