1.0 2011-09-21 00:24:42 UTC 2015-10-09 22:33:12 UTC FDB023102 Chalcone Chalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are known collectively as chalcones. They show antibacterial, antifungal, antitumor and anti-inflammatory properties. They are also intermediates in the biosynthesis of flavonoids, which are substances widespread in plants and with an array of biological activities. Chalcones are also intermediates in the Auwers synthesis of flavones.Chalcones can be prepared by an aldol condensation between a benzaldehyde and an acetophenone in the presence of sodium hydroxide as a catalyst. This reaction has been found to work in without any solvent at all - a solid-state reaction.[2] The reaction between substituted benzaldehydes and acetophenones has been used to demonstrate green chemistry in undergraduate chemistry education.[3] In a study investigating green chemistry synthesis, chalcones were also synthesized from the same starting materials in high temperature water (200 to 350 degree centigrade).[4] [HMDB] (2E)-1,3-Diphenyl-2-propen-1-one (e)-1,3-Diphenyl-2-propen-1-one (e)-Benzylideneacetophenone (e)-Chalcone 1-Benzoyl-1-phenylethene 1-Benzoyl-2-phenylethene 1-Benzoyl-2-phenylethylene 1-Phenyl-2-benzoylethylene 1, 3-Diphenyl-1-propen-3-one 1,3-Diphenyl-2-propen-1-one 1,3-Diphenyl-2-propenone 1,3-Diphenylpropenone 2-Benzalacetophenone 2-Benzylideneacetophenone 3-phenyl-Acrylophenone 3-Phenylacrylophenone a-Benzylideneacetophenone alpha-Benzylideneacetophenone b-Benzoylstyrene b-Phenylacrylophenone Benzalacetophenone Benzylideneacetophenone Benzylidenecetophenone beta-Benzoylstyrene beta-Phenylacrylophenone chalcone (ACD/Name 4.0) Chalkone Cinnamophenone Phenyl (e)--2-phenylethenyl ketone Phenyl 2-phenylvinyl ketone Phenyl styryl ketone Phenyl trans-styryl ketone Styryl phenyl ketone trans-Benzalacetophenone trans-Benzylideneacetophenone C15H12O 208.2552 208.088815006 (2E)-1,3-diphenylprop-2-en-1-one trans-chalcone 94-41-7 O=C(\C=C\C1=CC=CC=C1)C1=CC=CC=C1 InChI=1S/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H/b12-11+ DQFBYFPFKXHELB-VAWYXSNFSA-N belongs to the class of organic compounds known as retrochalcones. These are a form of normal chalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions. Retrochalcones Organic compounds Phenylpropanoids and polyketides Linear 1,3-diarylpropanoids Chalcones and dihydrochalcones Aromatic homomonocyclic compounds Acryloyl compounds Aryl ketones Benzoyl derivatives Enones Hydrocarbon derivatives Organic oxides Styrenes Acryloyl-group Alpha,beta-unsaturated ketone Aromatic homomonocyclic compound Aryl ketone Benzenoid Benzoyl Enone Hydrocarbon derivative Ketone Monocyclic benzene moiety Organic oxide Organic oxygen compound Organooxygen compound Retrochalcone Styrene chalcone Solid logp 3.63 ALOGPS logs -4.53 ALOGPS solubility 6.16e-03 g/l ALOGPS logp 3.89 ChemAxon pka_strongest_acidic 16.91 ChemAxon pka_strongest_basic -7.3 ChemAxon iupac (2E)-1,3-diphenylprop-2-en-1-one ChemAxon average_mass 208.2552 ChemAxon mono_mass 208.088815006 ChemAxon smiles O=C(\C=C\C1=CC=CC=C1)C1=CC=CC=C1 ChemAxon formula C15H12O ChemAxon inchi InChI=1S/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H/b12-11+ ChemAxon inchikey DQFBYFPFKXHELB-VAWYXSNFSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 66.88 ChemAxon polarizability 23.72 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::NmrTwoD 1858 Specdb::NmrOneD 1923 Specdb::CMs 829 Specdb::CMs 830 Specdb::CMs 1745 Specdb::CMs 16820 Specdb::CMs 27224 Specdb::CMs 27869 Specdb::CMs 30829 Specdb::CMs 30830 Specdb::CMs 31438 Specdb::CMs 166253 Specdb::MsIr 1867 Specdb::MsIr 1868 Specdb::MsMs 2185 Specdb::MsMs 2186 Specdb::MsMs 2187 Specdb::MsMs 5829 Specdb::MsMs 5830 Specdb::MsMs 5833 Specdb::MsMs 303166 Specdb::MsMs 303167 Specdb::MsMs 303168 Specdb::MsMs 346057 Specdb::MsMs 346058 Specdb::MsMs 346059 Specdb::MsMs 374801 Specdb::MsMs 447938 Specdb::MsMs 451484 Specdb::MsMs 2233697 Specdb::MsMs 2233745 Specdb::MsMs 2235182 Specdb::MsMs 2235229 Specdb::MsMs 2252530 Specdb::MsMs 2252643 Specdb::MsMs 2253819 Specdb::MsMs 2254572 Specdb::MsMs 2254679 Specdb::MsMs 2255906 HMDB03066 27618 #<Reference:0x000055ce31bce940> bitter