Chalcone

The title of this article is ambiguous. Further meanings are listed under Chalcone (disambiguation) .

Structural formula
Chalcone, ( E ) -isomer
General
Surname	Chalcone
other names	1,3-diphenyl-2-propen-1-one Benzylidene acetophenone Phenyl styryl ketone
Molecular formula	C 15 H 12 O
Brief description	pale yellow prisms
External identifiers / databases
CAS number 94-41-7 (mixture of isomers) 614-47-1 [ (E) -isomer] EC number 202-330-2 ECHA InfoCard 100.002.119 PubChem 637760 ChemSpider 6921 Wikidata Q899416
properties
Molar mass	208.26 g mol −1
Physical state	firmly
density	1.07 g cm −3
Melting point	59 ° C ( (E) -isomer) 57.5 ° C (mixture)
boiling point	346.5 ° C (mixture)
Vapor pressure	14 m Pa (25 ° C) (mixture)
solubility	soluble in diethyl ether , chloroform , benzene , carbon disulfide slightly soluble in ethanol practically insoluble in water (92.9 mg l −1 at 25 ° C)
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 302-319-335 P: 261-305 + 351 + 338
Toxicological data	56 mg kg −1 ( LD 50 ,  mouse ,  iv , mixture) > 500 mg kg −1 ( LD 50 ,  rat ,  oral , mixture) 1048 mg kg −1 ( LD 50 ,  mouse ,  oral , ( E ) -Chalcon)
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Chalcone is an aromatic unsaturated ketone that forms the basic substance of many important biologically active compounds, the so-called chalcones . The substance exists in two different isomers , which differ in their configuration with regard to the double bond.

Manufacturing

Chalcone can be made from benzaldehyde , acetophenone, and a base such as sodium hydroxide by aldol condensation .

use

Chalcone is used in perfumery . Derivatives with hydroxyl groups and halogens in the benzene nuclei have a bacteriostatic effect . Dihydro-chalcone derivatives of naringin and neohesperidin have a sweetener character (see Neohesperidin-dihydrochalcone ). Dihydrochalcones occur as ingredients in plants.

Derivatives

Chalcone can be substituted in several positions. For example, isoliquiritigenin , a natural product , is hydroxylated at positions 2 ', 4' and 4 . The xanthohumol found in hops ( Humulus lupulus ) is a multiply substituted chalcone. The hydroxylated chalcones also include robtein , butein and pedicin .

• 

  Locants at chalconies

• 

  Xanthohumol is a bitter substance from hops

See also

• Anthocyanins: properties
• Anthocyanins: biosynthesis
• Flavonoids: biosynthesis
• Mosses: Ingredients
• Phlorizin
• Cinnamic acid: biosynthesis

Individual evidence

1. ↑ ^{a b c d e f} Entry on chalcone. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.
2. ↑ Entry on (E) -Chalcones in the ChemIDplus database of the United States National Library of Medicine (NLM)
3. ↑ ^{a b c d} Entry on Chalcones in the ChemIDplus database of the United States National Library of Medicine (NLM)
4. ↑ ^{a b} Datasheet 1,3-Diphenyl-2-propenone from Sigma-Aldrich , accessed on March 16, 2011 ( PDF ).
5. ^ US Army Armament Research & Development Command , Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX # 04476
6. ^ National Academy of Sciences , National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, p. 28, 1953.
7. ↑ José A. González, Ana Estévez-Braun: Effect of (E) -Chalcone on Potato-Cyst Nematodes (Globodera pallida and G. rostochiensis). In: Journal of Agricultural and Food Chemistry . 46, 1998, p. 1163, doi : 10.1021 / jf9706686 .
8. ^ Wissenschaft-Online-Lexika: Entry on Chalcon in the Lexikon der Chemie , accessed August 26, 2008.