Dihydrochalcone

Last updated
Dihydrochalcone
Chemical structure of dihydrochalcone Dihydrochalcone alternate.svg
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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 Yes check.svgY
    Key: QGGZBXOADPVUPN-UHFFFAOYSA-N Yes check.svgY
  • C1=CC=C(C=C1)CCC(=O)C2=CC=CC=C2
Properties
C15H14O
Molar mass 210.27 g/mol
Appearancewhite 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

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

Neohesperidin dihydrochalcone is a commercial artificial sweetener that features the dihydrochalcone substituent. Neohesperidin dihydrochalcone.png
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 . [3]

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. ↑ Pratter, Paul J. (1981). "Neohesperidin dihydrochalcone: an updated review on a naturally derived sweetener and flavor potentiator" (PDF). Perfumer & Flavorist. 5: 12–18.
  3. ↑ 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


This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.