3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one

• ChemBase ID: 5444
• Molecular Formular: C15H14O5
• Molecular Mass: 274.26866
• Monoisotopic Mass: 274.08412355
• SMILES: c1c(cc(c(c1O)C(=O)CCc1ccc(cc1)O)O)O
• Canonical SMILES: Oc1ccc(cc1)CCC(=O)c1c(O)cc(cc1O)O
• InChI: InChI=1S/C15H14O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-2,4-5,7-8,16-17,19-20H,3,6H2
• InChIKey: VGEREEWJJVICBM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
• IUPAC Traditional name: dihydronaringenin; phloretin; 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
• Synonyms: Floretin; NSC 407292; Naringenin Dihydrochalcone; RJC 02792; β-(p-Hydroxyphenyl)phloropropiophenone; Dihydronaringenin; Phloretol; Phloretin; β-(4-Hydroxyphenyl)-2,4,6-trihydroxypropiophenone; 2′,4′,6′-Trihydroxy-3-(4-hydroxyphenyl)propiophenone; Phloretin; 3-(4-HYDROXYPHENYL)-1-(2,4,6-TRIHYDROXYPHENYL)PROPAN-1-ONE; 2',4',6'-Trihydroxy-3-(4-hydroxyphenyl)-propiophenone; Naringenin chalcone; β-(4-Hydroxyphenyl)-2,4,6-trihydroxypropiophenone; 3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanone; 2',4',6'-Trihydroxy-3-(4-hydroxyphenyl)propiophenone; Asebogenol; Dihydronarigenin; 根皮素

Database IDs

• CAS Number: 60-82-2
• EC Number: 200-488-7
• MDL Number: MFCD00002288
• Beilstein Number: 1887240
• Merck Index: 147326
• PubChem SID: 24278652; 24887442; 99444281; 160968872
• PubChem CID: 4788
• Chemspider ID: 4624
• Unique Ingredient Identifier: S5J5OE47MK
• Wikipedia Title: Phloretin

CALCULATED PROPERTIES

JChem

• Acid pKa: 7.958485
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 3.8940427
• LogD (pH = 7.4): 3.7892191
• Log P: 3.8955405
• Molar Refractivity: 73.7073 cm^3
• Polarizability: 27.944435 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.23
• LOG S: -3.32
• Solubility (Water): 1.32e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: Light Tan Solid; Powder
• Melting Point: ~260 °C; >262°C (dec.); 260-262°C (decomposes); 260-262°C(dec); ca 263°C dec.

Safety Information

• Storage Condition: -20°C; 2-8°C; Refrigerator
• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Antioxidant; Inhibits the stimulation of cAMP accumulation by prostaglandins; Prostanoid receptor antagonist

Product Information

• Purity: ≥98.0% (TLC); ≥99%; 98%
• Salt Data: Free Base
• Biological Source: Found in free state in Helichrysum splendidum
• Application(s): Antibacterial; Antioxidant
• Empirical Formula (Hill Notation): C15H14O5

DETAILS

MP Biomedicals - 02191511

Crystalline

DrugBank - DB07810

Drug information: experimental

Selleck Chemicals - S2342

Research Area: Inflammation
Biological Activity:
Phloretin(Dihydronaringenin) is a dihydrochalcone, a type of polyphenol. It is the phloroglucin ester of paraoxyhydratropic acid. It can be found in apple tree leaves. Phloretin hydrolase uses phloretin and water to produce phloretate and phloroglucinol. [1]

Toronto Research Chemicals - P339000

The aglucon of Phlorizin. A glucose transport inhibitor. Also inhibits protein kinase C and has been shown to inhibit the entry of five enveloped viruses into human fibroblasts.

Sigma Aldrich - 79310

General description
Major polyphenol found in apple; aglycone of phloridzin.
Biochem/physiol Actions
Reacts with vic-dicarbonyl compounds such as glyoxal and methylglyoxal, preventing cytotoxic conjugation with biological macromolecules.1

Sigma Aldrich - P7912

Biochem/physiol Actions
Blocks L-type Ca2+ channels; activates Ca2+-activated K+ channels in amphibian myelinated nerve fibers. Monocarboxylate transporter inhibitor.
Reacts with vic-dicarbonyl compounds such as glyoxal and methylglyoxal, preventing cytotoxic conjugation with biological macromolecules.1
General description
Major polyphenol found in apple; aglycone of phloridzin.

REFERENCES

• Inflammation
• Constantinescu, S.N., et al.: FEBS Lett., 292, 31 (1991)
• Mann, J., et al.: Appl. Physiol., 71, 410 (1991)
• Benga, G., et al.: Eur. J. Cell Biol., 59, 219 (1991)
• Kitanaka, J., et al.: J. Neurochem., 60, 704 (1991)
• Wang, X., et al.: Biochem. J., 290, 249
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 866B, (nmr)
• Eykman, J.F., Ber., 1883, 16, 2769, (isol)
• Zempln, R. et al., Ber., 1942, 75, 645; 1298, (synth)
• Murakami, S., Yakugaku Zasshi, 1955, 75, 573; 603, (isol)
• Batterham, T.J. et al., Aust. J. Chem., 1964, 17, 428, (pmr)
• Farkas, L. et al., Chem. Ber., 1965, 98, 2926, (synth)
• King, B. et al., Phytochemistry, 1975, 14, 1448, (deriv)
• Mancini, S.D. et al., J. Nat. Prod., 1979, 42, 483, (isol)
• Bohlmann, F. et al., Phytochemistry, 1979, 18, 885, (isol)
• Braz Filho, R. et al., Phytochemistry, 1980, 19, 1195, (derivs)
• Hufford, C.D. et al., Phytochemistry, 1980, 19, 2036, (cmr)
• Hutz, C. et al., Z. Naturforsch., C, 1982, 37, 337, (isol)
• Bohm, A., The Flavonoids: Advances in Research since 1980, (Ed. Harborne, J.B.), Chapman and Hall, London, 1988, 346, (rev)
• Barrero, A.F., J. Nat. Prod., 1997, 60, 65, (cmr)