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]
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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)
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ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.150.317 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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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Natural dihydrochalcones
edit- Aspalathin, a C-linked dihydrochalcone glucoside found in rooibos, a common herbal tea
- Naringin dihydrochalcone, an artificial sweetener derived from naringin
- Neohesperidin dihydrochalcone, an artificial sweetener derived from citrus
- Nothofagin, a C-linked phloretin glucoside found in rooibos
- Phloretin
- Isosalipurpurin
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
edit- ^ 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.
- ^ 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