Dihydrochalcone
Chemical compound
From Wikipedia, the free encyclopedia
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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| 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 Ï-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 | 72â75 °C (162â167 °F; 345â348 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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The formation of dihydrochalcones removes the conjugation between the two ring systems (via the ketone) when the double bond is abolished. This causes the visible color of the chalcones to disappear in their dihydrochalcone derivatives.[2]
Natural dihydrochalcones
- 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 (3â²,5â²-dihydroxy-2â²,4â²,6â²-trimethoxydihydrochalcone (methyl linderone) and 2â²-hydroxy-3â²,4â²,5â²,6â²-tetramethoxydihydrochalcone (dihydrokanakugiol) can be found in twigs of Lindera lucida.[3]
