Phloretin

Base Information

• Chemical Name: Phloretin
• CAS No.: 60-82-2
• Molecular Formula: C15H14O5
• Molecular Weight: 274.273
• Hs Code.: 29145090
• European Community (EC) Number: 200-488-7
• NSC Number: 407292
• UNII: S5J5OE47MK
• DSSTox Substance ID: DTXSID6022393
• Nikkaji Number: J4.808I
• Wikipedia: Phloretin
• Wikidata: Q2268463
• RXCUI: 1368167
• Pharos Ligand ID: MN9LWXHJDSQR
• Metabolomics Workbench ID: 27000
• ChEMBL ID: CHEMBL45068
• Mol file: 60-82-2.mol

Synonyms:Phloretin

Chemical Property of Phloretin

Chemical Property:

• Appearance/Colour: Crystalline Solid
• Vapor Pressure: 1.4E-05mmHg at 25°C
• Melting Point: ~260 °C
• Refractive Index: 1.573-1.575
• Boiling Point: 534.4 °C at 760 mmHg
• PKA: 7.16±0.40(Predicted)
• Flash Point: 291.1 °C
• PSA: 97.99000
• Density: 1.429 g/cm³
• LogP: 2.32450
• Storage Temp.: 2-8°C
• Solubility.: Acetonitrile (Slightly), Methanol (Slightly)
• Water Solubility.: soluble
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 274.08412354
• Heavy Atom Count: 20
• Complexity: 312

Purity/Quality:

98% ^*data from raw suppliers

Phloretin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1CCC(=O)C2=C(C=C(C=C2O)O)O)O
• Uses: Phloretin 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 As glucose transport inhibitor, Phloretin can inhibits protein kinase C and has been shown to inhibit the entry of five enveloped viruses into human fibroblasts.

Technology Process of Phloretin

There total 40 articles about Phloretin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

(E)-3-(4-benzyloxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one → 3-(4-Hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-on (60-82-2)

Guidance literature:

With triethylsilane; palladium 10% on activated carbon; In methanol; ethyl acetate; at 20 ℃; for 0.166667h;

DOI:10.1021/acs.jmedchem.6b01134

Reference yield: 90.0%

phloridizin (60-81-1,6426-09-1,40816-73-7,130549-93-8,138665-98-2) → 3-(4-Hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-on (60-82-2)

Guidance literature:

With hydrogenchloride; water; In ethanol; at 90 ℃; for 3h;

DOI:10.1016/j.bmcl.2008.11.112

Reference yield: 84.0%

naringenin chalcone (25515-46-2) → 3-(4-Hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-on (60-82-2)

Guidance literature:

With Rhodococcus sp. DSM 364; In acetone; at 28 ℃; for 72h; chemoselective reaction; Microbiological reaction;

DOI:10.1016/j.molcatb.2013.09.009

upstream raw materials:

3,5-dihydroxyphenol

3-(p-hydroxyphenyl)propiononitrile

3-(4-acetoxyphenyl)propanenitrile

4'-(β-D-glucopyranosyloxy)-2',4”,6'-trihydroxydihydrochalcone

Downstream raw materials:

acetic acid 4-[3-oxo-3-(2,4,6-triacetoxy-phenyl)propyl]phenyl ester

5,7-dihydroxy-3-[(4-hydroxyphenyl)methyl]-4H-chromen-4-one

4-hydroxyphenylpropionic acid

3,5-dihydroxyphenol

Refernces

• 1、 Williams. "". . p. 1583. Retrieved 1967.
• 2、 Cala Peralta, Antonio,Helesbeux, Jean-Jacques,Hoff, Daniel,Hofstetter, Robert Klaus,Jordan, Paul M.,Koeberle, Andreas,Kretzer, Christian,Meyer, Katharina P. L.,Richomme, Pascal,Schuster, Daniela,Seraphin, Denis,Stuppner, Hermann,Temml, Veronika,Viault, Guillaume,Werner, Markus,Werz, Oliver. "Natural chalcones elicit formation of specialized pro-resolving mediators and related 15-lipoxygenase products in human macrophages". . . Retrieved 2021/12/24.
• 3、 -. "Quinoid dihydrochalcone dicarbonyl glycoside compound with glucose on A ring, preparation method and neuroprotective activity thereof". Paragraph 0070-0075. . Retrieved 2020/09/23.