カルコン

解説1,3-diphenyl-2-propen-1-one．C15H12O(208.25)．天然には存在せず，アセトフェノンとベンズアルデヒドの縮合により合成される．"橙黄色の柱状晶．融点58 ℃，沸点345 ℃．d624 1.071．n62D 1.646．濃硫酸と無水酢酸により二量体をつくる．広義では，カルコンは天然にある上記化合物とヒドロキシ誘導体を総称し，橙黄色または橙赤色の色素である．カルタミン，ロットレリン，ブテインなどがその例である．皮膚刺激性がある．[CAS 94-41-7]森北出版「化学辞典（第2版）

用途カルコンは，芳香族ケトンに属す有機化合物の一つ。狭義にはベンザルアセトフェノンと呼ばれ、天然に存在せず、ベンズアルデヒドとアセトンから合成される。広義にはその誘導体も含まれ、天然にさまざまな植物色素として存在し、各種フラボノイドの生合成にかかわる。抗菌性、抗炎症作用を示すものもがある。

説明Chalcone is the organic compound C6H5C(O)CH=CHC6H5. It is an α,β-unsaturated ketone. A variety of important biological compounds are known collectively as chalcones or chalconoids.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.

使用Chalcone is used in the preparation of pharmacologically-interesting heterocyclic systems like pyrazolines and pyrimidines. It also inhibits the proliferation of human breast cancer cell lines, MCF-7 and MDA-MB-231 by inducing apoptosis and blocking cell cycle progression in the G2/M phase.

製造方法Chalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are known collectively as chalcones.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 without any solvent at all - a solid-state reaction. The reaction between substituted benzaldehydes and acetophenones has been used to demonstrate green chemistry in undergraduate chemistry education.In a study investigating green chemistry synthesis, chalcones were also synthesized from the same starting materials in high temperature water (200 to 350 °C).

純化方法Crystallise it from EtOH by warming to 50o (about 5mL/g), iso-octane, or toluene/pet ether, or recrystallise it from MeOH, and then twice from hexane. SKIN IRRITANT. [Beilstein 7 IV 1658.]