Basic information
- Standard SMILES
O=C(CCc1ccc(O)cc1)c1c(O)cc(O)cc1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O- InChIKey
IOUVKUPGCMBWBT-QNDFHXLGSA-N- Molecular formula
- C21H24O10
- Average molar mass
- 436.4 g/mol
- Monoisotopic mass
- 436.13694697
Overview
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 an antioxidant and a plant metabolite. It is an aryl beta-D-glucoside, a monosaccharide derivative and a member of dihydrochalcones. It is functionally related to a phloretin.
Names & identifiers
- Preferred name
- Phlorizin
- IUPAC
- 1-[2,4-dihydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxyphenyl)propan-1-one
Names & synonyms
PhlorizinPhlorhizinPhlorizosideFloridzinPhlorrhizinPhloretin 2'-glucosidePhlorrhizenPhloridzinumPhloretin-2'-O-beta-glucosideCU9S17279XNSC-2833phloretin 2'-O-glucoside
Show more names
1-(2,4-dihydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(4-hydroxyphenyl)propan-1-one2'-(beta-D-Glucopyranosyloxy)-4',6'-dihydroxy-3-(4-hydroxyphenyl)propiophenoneCHEBI:8113DTXSID30753391-Propanone, 1-(2-(beta-D-glucopyranosyloxy)-4,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1-Propanone, 1-[2-(beta-D-glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-[2,4-dihydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxyphenyl)propan-1-onePhloridzin Phenolic
Database identifiers
- CAS
60-81-1- PubChem CID
- 6072
- DTXSID
DTXSID3075339- ChEMBL
CHEMBL245067- ChEBI
CHEBI:8113- UNII
- CU9S17279X
- Nikkaji
- J4.807K
Properties
Computed structural properties
- XLogP
- 1.2
- Topological polar surface area
- 177 Ų
- Hydrogen bond donors
- 7
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 7
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 581
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Plant Oils and Extracts
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Chalcones and dihydrochalcones [PK1212]
Solubility1 mg/mL at 22 °C
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point110.0 °C
Physical Description
Off-white powder; [ChromaDex MSDS]
Solid
Collision Cross Section
194.4 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
192.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Safety & regulation
Hazard information
Hazards SummaryIntraperitoneal
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
UsesFound in all parts of the apple tree except the mature fruit; Used in animal experiments to produce glycosuria; [Merck Index]
Related reactions
2 records
Linked notes
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