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60-82-2 molecular structure
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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 and InChIs

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

Cite this record

CBID:5444 http://www.chembase.cn/molecule-5444.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

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

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 7.958485  H Acceptors
H Donor LogD (pH = 5.5) 3.8940427 
LogD (pH = 7.4) 3.7892191  Log P 3.8955405 
Molar Refractivity 73.7073 cm3 Polarizability 27.944435 Å3
Polar Surface Area 97.99 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.23  LOG S -3.32 
Solubility (Water) 1.32e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Ethanol expand Show data source
Methanol expand Show data source
Apperance
Light Tan Solid expand Show data source
Powder expand Show data source
Melting Point
~260 °C expand Show data source
>262°C (dec.) expand Show data source
260-262°C (decomposes) expand Show data source
260-262°C(dec) expand Show data source
ca 263°C dec. expand Show data source
Storage Condition
-20°C expand Show data source
2-8°C expand Show data source
Refrigerator expand Show data source
Storage Warning
IRRITANT expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26 expand Show data source
26-37 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Mechanism of Action
Antioxidant expand Show data source
Inhibits the stimulation of cAMP accumulation by prostaglandins expand Show data source
Prostanoid receptor antagonist expand Show data source
Purity
≥98.0% (TLC) expand Show data source
≥99% expand Show data source
98% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Biological Source
Found in free state in Helichrysum splendidum expand Show data source
Application(s)
Antibacterial expand Show data source
Antioxidant expand Show data source
Empirical Formula (Hill Notation)
C15H14O5 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB07810 external link
Drug information: experimental
Selleck Chemicals - S2342 external link
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]
Sigma Aldrich - P7912 external link
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.
Sigma Aldrich - 79310 external link
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
Toronto Research Chemicals - P339000 external link
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.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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