Dihydrochalcone

{{chembox | Watchedfields = changed | verifiedrevid = 460786940 | Name = Dihydrochalcone | ImageFile = Dihydrochalcone alternate.svg | ImageName = Chemical structure of dihydrochalcone | PIN = 1,3-Diphenylpropan-1-one | OtherNames = Hydrochalcone Benzylacetophenone Hydrocinnamophenone 3-Phenylpropiophenone Phenethyl phenyl ketone Phenyl phenethyl ketone β-Phenylpropiophenone 1,3-Diphenyl-1-propanone ω-Benzyl acetophenone |Section1={{Chembox Identifiers | CASNo = 1083-30-3 | CASNo_Ref = {{cascite|correct|??}}= | UNII_Ref = {{fdacite|correct|FDA}} | UNII = H5W525SX7Q | CASNoOther = | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 490512 | PubChem = 64802 | SMILES = C1=CC=C(C=C1)CCC(=O)C2=CC=CC=C2 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 58334 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = QGGZBXOADPVUPN-UHFFFAOYSA-N | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI=1S/C15H14O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-10H,11-12H2 | MeSHName = }} |Section2={{Chembox Properties | Formula = C15H14O | MolarMass = 210.27 g/mol | Appearance = white solid | Density = 1.0614 g/cm3 | MeltingPtC = 72-75 | BoilingPt = | Solubility = }} }}

'''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.<ref>{{cite journal |doi=10.1002/(SICI)1097-0010(20000515)80:7<1073::AID-JSFA568>3.0.CO;2-B|title=Flavanones, Chalcones and Dihydrochalcones - Nature, Occurrence and Dietary Burden|year=2000|last1=Tomás-Barberán|first1=Francisco A.|last2=Clifford|first2=Michael N.|journal=Journal of the Science of Food and Agriculture|volume=80|issue=7|pages=1073–1080}}</ref>

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.<ref>{{cite journal |last=Pratter |first=Paul J. |title=Neohesperidin dihydrochalcone: an updated review on a naturally derived sweetener and flavor potentiator |year=1981 |journal=Perfumer & Flavorist |volume=5 |pages=12–18 |url=https://img.perfumerflavorist.com/files/base/allured/all/document/2016/04/pf.8053.pdf}}</ref>

==Natural dihydrochalcones== [[file:Neohesperidin_dihydrochalcone.png|thumb|left|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''.<ref>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}}</ref> ==Uses== A known use of dihydrochalcone is in the synthesis of 3-phenylindene [1961-97-3].<ref>{{cite journal | vauthors = Saito S, Sato Y, Ohwada T, Shudo K | title = Friedel-Crafts-type cyclodehydration of 1,3-diphenyl-1-propanones. Kinetic evidence for the involvement of dication. | journal = Journal of the American Chemical Society | date = March 1994 | volume = 116 | issue = 6 | pages = 2312-2317 | doi = 10.1021/ja00085a010 }}</ref> This in-turn finds application in the synthesis of Indriline & Pyrophendane [7009-69-0]. ==References== {{reflist}}

Category:Dihydrochalcones