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Dihydrochalcone

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Dihydrochalcone
Chemical structure of dihydrochalcone
Names
Preferred IUPAC name
1,3-Diphenylpropan-1-one
Other names
Hydrochalcone
Benzylacetophenone
Hydrocinnamophenone
3-Phenylpropiophenone
Phenethyl phenyl ketone
Phenyl phenethyl ketone
β-Phenylpropiophenone
1,3-Diphenyl-1-propanone
ω-Benzyl acetophenone
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.150.317 Edit this at Wikidata
UNII
  • InChI=1S/C15H14O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-10H,11-12H2 checkY
    Key: QGGZBXOADPVUPN-UHFFFAOYSA-N checkY
  • C1=CC=C(C=C1)CCC(=O)C2=CC=CC=C2
Properties
C15H14O
Molar mass 210.27 g/mol
Appearance white solid
Density 1.0614 g/cm3
Melting point 72–75 °C (162–167 °F; 345–348 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dihydrochalcone (DHC) is the organic compound with the formula C6H5C(O)(CH2)2C6H5. It is the reduced derivative of chalcone (C6H5C(O)(CH)2C6H5). It is a white solid that is soluble in many organic solvents. Dihydrochalcone per se is often minor significance, but some derivatives occur in nature and have attracted attention as drugs.[1]

Natural dihydrochalcones

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Neohesperidin dihydrochalcone is a commercial artificial sweetener that features the dihydrochalcone substituent.

Dihydrochalcones (3′,5′-dihydroxy-2′,4′,6′-trimethoxydihydrochalcone (methyl linderone) and 2′-hydroxy-3′,4′,5′,6′-tetramethoxydihydrochalcone (dihydrokanakugiol) can be found in twigs of Lindera lucida.[2]

References

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  1. ^ Tomás-Barberán, Francisco A.; Clifford, Michael N. (2000). "Flavanones, Chalcones and Dihydrochalcones - Nature, Occurrence and Dietary Burden". Journal of the Science of Food and Agriculture. 80 (7): 1073–1080. doi:10.1002/(SICI)1097-0010(20000515)80:7<1073::AID-JSFA568>3.0.CO;2-B.
  2. ^ A dihydrochalcone from Lindera lucida. Yuan-Wah Leong, Leslie J. Harrison, , Graham J. Bennett, Azizol A. Kadir and Joseph D. Connolly, Phytochemistry, Volume 47, Issue 5, March 1998, Pp. 891-894, doi:10.1016/S0031-9422(97)00947-3