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614-47-1

中文名稱 查耳酮
英文名稱 trans-Chalcone
CAS 614-47-1
EINECS 編號 202-330-2
分子式 C15H12O
MDL 編號 MFCD00003082
分子量 208.26
MOL 文件 614-47-1.mol
更新日期 2025/01/23 16:18:13
614-47-1 結構式 614-47-1 結構式

基本信息

中文別名
查耳酮
苯丙烯酰苯
苯基苯乙烯基甲酮
苯蘇合香稀甲酮
苯乙烯基本基甲酮
芐差苯乙酮
亞芐基代苯乙酮
查爾酮
1,3-二苯-2-丙烯-1-酮
1,3-二苯基-2-丙烯-1-酮
反-查耳酮,苯乙烯基苯基酮
英文別名
1,3-DIPHENYL-2-PROPEN-1-ONE
1,3-DIPHENYL-2-PROPEN-I-ONE
1,3-DIPHENYL-2-PROPENONE
1,3-DIPHENYL-3-PROPEN-1-ONE
1,3-DIPHENYLPROP-2-EN-1-ONE
2-BENZALACETOPHENONE
2-BENZYLIDENEACETOPHENONE
(2E)-1,3-DIPHENYLPROP-2-EN-1-ONE
3-PHENYLACRYLOPHENONE
BENZALACETOPHENONE
BENZYLIDENEACETOPHENONE
BENZYLIDINEACETOPHENONE
CHALCONE
CHALKONE
(E)-CHALCONE
PHENYL STYRYL KETONE
TRANS-BENZYLIDENEACETOPHENONE
TRANS-CHALCONE
(e)-1,3-diphenyl-2-propen-1-one
(e)-benzylideneacetophenone
所屬類別
有機原料:酮類化合物

物理化學性質

熔點55-59 °C
沸點208 °C25 mm Hg(lit.)
密度1.0712
折射率1.5361 (estimate)
閃點>230 °F
儲存條件Sealed in dry,Room Temperature
溶解度可溶于氯仿(少許)
形態(tài)固體
顏色淡黃色
氣味 (Odor)at 100.00 %. floral balsam herbal
香型floral
水溶解性Soluble in chloroform, ether, benzene, and ethanol (slightly). Insoluble in water.
Merck14,2037
BRN509985
LogP4.013 (est)
CAS 數(shù)據(jù)庫614-47-1(CAS DataBase Reference)
NIST化學物質信息Benzalacetophenone(614-47-1)

安全數(shù)據(jù)

危險性符號(GHS)GHS hazard pictograms
GHS07
警示詞警告
危險性描述H302-H319-H335
危險品標志Xn,Xi
危險類別碼R22-R36/37
安全說明S22-S36/37/39-S45
WGK Germany3
RTECS號UD5576750
海關編碼29143990

化學品安全說明書(MSDS)

常見問題列表

應用
反式-查耳酮是一種不飽和酮類化合物,淺黃色斜方棱柱體結晶。有文獻報道其是一種小分子GPR52拮抗劑。反式-查耳酮可由苯乙酮和苯甲醛一步反應制備得到。
制備

614-47-1的合成

在氮氣下,將[Ni(dmpymt)2] 6(5 mol%Ni),KOH(1.0 mmol),苯甲醇(1.5 mmol)和1-苯基乙醇(1.0 mmol)與甲苯(2.5 mL)/ t-BuOH(0.5 mL)加入50毫升Schlenk試管中,將試管置于70°C油浴中,在緩慢,穩(wěn)定的氮氣流中攪拌混合物36小時,將混合物冷卻至室溫,加水(10毫升)。 用CH2Cl2(3×10 mL)萃取水溶液,用無水Na2SO4干燥合并的萃取液,除去溶劑,在短時間快速柱色譜上純化粗產物得到反式-查耳酮。

生物活性
trans-Chalcone 是從Aronia melanocarpa 果皮中分離出來的,是類黃酮前體的雙酚核心結構。trans-Chalcone 是有效的脂肪酸合酶 (FAS) 和 α-淀粉酶 (b>α-amylase) 抑制劑。trans-Chalcone 引起細胞周期停滯并誘導乳腺癌細胞系 MCF-7 凋亡。trans-Chalcone 具有抗真菌和抗癌活性。
體外研究

trans-Chalcone competitively inhibits porcine pancreatic α-amylase with a Ki of 48 μM.
trans-Chalcone (30.23-98.03 μM; 24 hours) induces cell cycle arrest and apoptosis in MCF-7 cells.
trans-Chalcone (30.23-98.03 μM; 24 hours) reduces the expression of the apoptosis-related protein Bcl-2 and induces the expression of the CIDEA gene.
trans-Chalcone (58.25 μM; 6, 24 hours) has greater inhibition of Bcl-2, induction of APAF1 and BAX, and strong induction of CIDEA in 24 hours.
trans-Chalcone (24 hours) inhibits MCF-7 cell viability (IC 20 =30.23 μM; IC 50 =58.25 μM; IC 80 =98.03 μM). trans-Chalcone (48 h) has IC 50 s of 41.53 μM and 48.41 μM for MCF-7 and 3T3 cell lines, respectively. trans-Chalcone exhibits a pronounced cytotoxicity activity.

Apoptosis Analysis

Cell Line: MCF-7 cell
Concentration: 30.23, 58.25, 98.03 μM
Incubation Time: 24 hours
Result: Induced apoptosis of the breast cancer cell line.

Cell Cycle Analysis

Cell Line: MCF-7 cell
Concentration: 30.23, 58.25, 98.03 μM
Incubation Time: 24 hours
Result: Caused cell cycle arrest in G1.

Western Blot Analysis

Cell Line: MCF-7 cell
Concentration: 20, 40, 80 μM
Incubation Time: 24, 48 hours
Result: Reduced the expression of the apoptosis-related protein Bcl-2 and induced the expression of the CIDEA gene.
There was marked degradation of cyclin D1 at 48 h.

RT-PCR

Cell Line: MCF-7 cell
Concentration: 58.25 μM
Incubation Time: 6, 24 hours
Result: Had greater inhibition of Bcl-2, induction of APAF1 and BAX, and strong induction of CIDEA in 24 hours.
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