HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Compound

Phlorizin

HCID 6072
New noteNew reactionRequest quotes
Print preview
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
60-81-1
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
English name
Phlorizin
Molecular formula
C21H24O10
Molecular weight
436.41

Names & synonyms

PhlorizinPhlorhizinPhlorizosideFloridzinPhlorrhizinPhloretin 2'-glucosidePhlorrhizenPhloridzinumPhloretin-2'-O-beta-glucosideCU9S17279XNSC-2833phloretin 2'-O-glucoside
Show more names
PHLORIDZINphlorizinephloridzinePHLORIDZIN DIHYDRATENSC 2833Phlorinin
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

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 · 2 items

Off-white powder; [ChromaDex MSDS]

Solid

Collision Cross Section · 2 items

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]

Physicochemical properties

Melting point
113 · 113-114 °C(lit.)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

Hazards SummaryIntraperitoneal

Safety data

F
3-10-23
wgk
3
rtecs
UC2080000
hs_code
29389090
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
26-36
Storage Class
11 - Combustible Solids
Hazard statements
H315-H319-H335
REACH Registrations
Active
Precautionary statements
P261-P305+P351+P338

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]
Applications · 3 items

UsesIt 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

Usesinduces experimental glucosuria, antifeedant

UsesSodium-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.

Additional notes

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

Related reactions

2 records
New reaction record
HRID 277444 reaction equation
HRID 277444As reactantuspto-grants-2002_03
HRID 1005646 reaction equation
HRID 1005646As reactantuspto-grants-2004_09

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
More actions
New noteNew reactionRequest quotes
ChEMBL
CHEMBL245067
ChEBI
CHEBI:8113
UNII
CU9S17279X
Nikkaji
J4.807K
Boiling point
468.89 °C · 468.89°C (rough estimate)
Density
1.3178 · 1.3178 (rough estimate)
refractive index
-54 ° · -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 · 7.15±0.40(Predicted)
color
Light Yellow to Tan
Merck
14 · 14,7327
Major Application
food and beverages
Cosmetics Ingredients Functions
SKIN CONDITIONING
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|
LogP
0.452 · 0.452 (est)
CAS DataBase Reference
60 · 60-81-1(CAS DataBase Reference)
FDA UNII
9 S17279X · CU9S17279X
EPA Substance Registry System
Phlorizin (60-81-1)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
261 · P261-P305+P351+P338
Hazard Codes
Xi
Risk Statements
36 · 36/37/38
Safety Statements
26 · 26-36
WGK Germany
3 · 3
RTECS
2080000 · UC2080000
F
3 · 3-10-23
HS Code
29389090 · 29389090
Storage Class
11 · 11 - Combustible Solids
REACH Registrations
Active