FComEx: Chalcone (PC000883)

Record Information

Version

1.0

Creation date

2015-10-09 22:33:12 UTC

Update date

2017-01-19 02:36:40 UTC

FoodComEx ID

PC000883

FoodDB Record

FDB023102

Chemical Information

Name

Chalcone

Description

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]

CAS Number

94-41-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2E)-1,3-Diphenyl-2-propen-1-one	hmdb
(e)-1,3-Diphenyl-2-propen-1-one	ChEBI
(e)-Benzylideneacetophenone	ChEBI
(e)-Chalcone	ChEBI
1-Benzoyl-1-phenylethene	hmdb
1-Benzoyl-2-phenylethene	hmdb
1-Benzoyl-2-phenylethylene	hmdb
1-Phenyl-2-benzoylethylene	hmdb
1, 3-Diphenyl-1-propen-3-one	hmdb
1,3-Diphenyl-2-propen-1-one	hmdb
1,3-Diphenyl-2-propenone	hmdb
1,3-Diphenylpropenone	hmdb
2-Benzalacetophenone	hmdb
2-Benzylideneacetophenone	hmdb
3-phenyl-Acrylophenone	hmdb
3-Phenylacrylophenone	hmdb
a-Benzylideneacetophenone	hmdb
alpha-Benzylideneacetophenone	hmdb
b-Benzoylstyrene	hmdb
b-Phenylacrylophenone	hmdb
Benzalacetophenone	hmdb
Benzylideneacetophenone	hmdb
Benzylidenecetophenone	hmdb
beta-Benzoylstyrene	hmdb
beta-Phenylacrylophenone	hmdb
chalcone (ACD/Name 4.0)	hmdb
Chalkone	hmdb
Cinnamophenone	hmdb
Phenyl (e)--2-phenylethenyl ketone	ChEBI
Phenyl 2-phenylvinyl ketone	hmdb
Phenyl styryl ketone	hmdb
Phenyl trans-styryl ketone	ChEBI
Styryl phenyl ketone	hmdb
trans-Benzalacetophenone	ChEBI
trans-Benzylideneacetophenone	ChEBI

Chemical Formula

C15H12O

IUPAC name

(2E)-1,3-diphenylprop-2-en-1-one

InChI Identifier

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+

InChI Key

DQFBYFPFKXHELB-VAWYXSNFSA-N

Isomeric SMILES

O=C(\C=C\C1=CC=CC=C1)C1=CC=CC=C1

Average Molecular Weight

208.2552

Monoisotopic Molecular Weight

208.088815006

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

Retrochalcones

Alternative Parents