Phloretin
Basic information
- CAS
60-82-2- Standard SMILES
O=C(CCc1ccc(O)cc1)c1c(O)cc(O)cc1O- InChIKey
VGEREEWJJVICBM-UHFFFAOYSA-N- Molecular formula
- C15H14O5
- Average molar mass
- 274.27 g/mol
- Monoisotopic mass
- 274.08412354
Overview
Phloretin is a member of the class of dihydrochalcones that is dihydrochalcone substituted by hydroxy groups at positions 4, 2', 4' and 6'. It has a role as an antineoplastic agent and a plant metabolite. It is functionally related to a dihydrochalcone.
Names & identifiers
- Preferred name
- Phloretin
- IUPAC
- 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
- English name
- Phloretin
- Molecular formula
- C15H14O5
- Molecular weight
- 274.27
Names & synonyms
phloretin60-82-2Dihydronaringenin3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-onePhloretol1-Propanone, 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-DTXSID6022393S5J5OE47MKFEMA NO. 4390NSC-4072922',4,4',6'-TetrahydroxydihydrochalconeDTXCID702393
Show more names
FloretinoretinRJC 02792PhloridinAsebogenol
CHEBI:172762',4,4',6'-Tetrahydroxy-DihydrochalconeRefChem:861869200-488-73-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanoneMFCD00002288NSC 407292Phloretin (Standard)
Database identifiers
- CAS
60-82-2- PubChem CID
- 4788
- DTXSID
DTXSID6022393- ChEMBL
CHEMBL45068- ChEBI
CHEBI:17276- UNII
- S5J5OE47MK
- EC Number
- 200-488-7
- Nikkaji
- J4.808I
Properties
Computed structural properties
- XLogP
- 2.6
- Topological polar surface area
- 98 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 312
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Chalcones and dihydrochalcones [PK1212]
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility
0.123 mg/mL at 16 °C
Slightly soluble in water
Sparingly soluble (in ethanol)
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point263.5 °C
Physical Description
Solid
Pearl white powder; Sweet aroma
Collision Cross Section
159.02 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
160.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 72.4% (118 of 163) of all reports.
Warning
H315 (27.6%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 163 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Hazard Classes and CategoriesSkin Irrit. 2 (27.6%)
Safety data
- F
- 3-10
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29145090
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 37/39-26-36
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
Chemistry & industry
Pharmacology
Metabolism/MetabolitesPhloretin has known human metabolites that include Phloretin, 4p-hydroxy-glucuronide and Phloretin, 2p-hydroxy-glucuronide.
Tissue LocationsFibroblasts
Cellular LocationsMembrane
Uses & manufacturing
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Applications
UsesPhloretin has been used:to study its effect on the 2-[N-(7-Nitrobenz-2-oxa-1,3-diazol-4-yl)amino]-2-deoxy-d-glucose (2-NBDG) and 2-[N-(7-Nitrobenz-2-oxa-1,3-diazol-4-yl)amino]-2-deoxy-l-glucose (2-NBDLG) uptaketo incubate microvesicles in order to inhibit GLUT1 (glucose transporter 1)-mediated transport in radioactive ligand up-take assayas a component of KRH buffer to stop glucose uptake by trophoblast cells in vitro
UsesAs glucose transport inhibitor, Phloretin can inhibits protein kinase C and has been shown to inhibit the entry of five enveloped viruses into human fibroblasts.
General DescriptionPhloretin is a dihydrochalcone flavonoid with antioxidant activity usually found in apples and apple-derived products. It is extensively used for peroxynitrite scavenging and the inhibition of lipid peroxidation. It has been found to inhibit the growth of several cancer cells and induce apoptosis of B16 melanoma and HL60 human leukemia cells.
Upstream & downstream products
Downstream products
Suppliers
Loading…
Open inquiries
Loading…
Related reactions
5 records
Compound notes
Loading…