Dihydrochalcone

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]

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
CAS Number	1083-30-3 Y=
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL490512 Y
ChemSpider	58334 Y
ECHA InfoCard	100.150.317
PubChem CID	64802
UNII	H5W525SX7Q Y
CompTox Dashboard (EPA)	DTXSID7061481
InChI 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 Y Key: QGGZBXOADPVUPN-UHFFFAOYSA-N Y
SMILES C1=CC=C(C=C1)CCC(=O)C2=CC=CC=C2
Properties
Chemical formula	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). Y verify (what is YN ?) Infobox references

Natural dihydrochalcones

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

• 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

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