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614-47-1

中文名称 查耳酮
英文名称 trans-Chalcone
CAS 614-47-1
EINECS 编号 202-330-2
分子式 C15H12O
MDL 编号 MFCD00003082
分子量 208.26
MOL 文件 614-47-1.mol
更新日期 2024/04/30 10:29:56
614-47-1 结构式 614-47-1 结构式

基本信息

中文别名
查耳酮
苯丙烯酰苯
苯基苯乙烯基甲酮
苯苏合香稀甲酮
苯乙烯基本基甲酮
苄差苯乙酮
亚苄基代苯乙酮
查尔酮
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
英文别名
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
所属类别
有机原料:酮类化合物

物理化学性质

熔点55-59 °C
沸点208 °C25 mm Hg(lit.)
密度1.0712
折射率1.5361 (estimate)
闪点>230 °F
储存条件Sealed in dry,Room Temperature
溶解度可溶于氯仿(少许)
形态固体
颜色淡黄色
气味 (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)
NIST化学物质信息Benzalacetophenone(614-47-1)

安全数据

危险性符号(GHS)
GHS07
警示词警告
危险性描述H302-H319-H335
危险品标志Xn,Xi
危险类别码R22-R36/37
安全说明S22-S36/37/39-S45
WGK Germany3
RTECS号UD5576750
海关编码29143990

化学品安全说明书(MSDS)

常见问题列表

应用
反式-查耳酮是一种不饱和酮类化合物,浅黄色斜方棱柱体结晶。有文献报道其是一种小分子GPR52拮抗剂。反式-查耳酮可由苯乙酮和苯甲醛一步反应制备得到。
制备

614-47-1的合成

在氮气下,将[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)与甲苯(2.5 mL)/ t-BuOH(0.5 mL)加入50毫升Schlenk试管中,将试管置于70°C油浴中,在缓慢,稳定的氮气流中搅拌混合物36小时,将混合物冷却至室温,加水(10毫升)。 用CH2Cl2(3×10 mL)萃取水溶液,用无水Na2SO4干燥合并的萃取液,除去溶剂,在短时间快速柱色谱上纯化粗产物得到反式-查耳酮。

生物活性
trans-Chalcone 是从Aronia melanocarpa 果皮中分离出来的,是类黄酮前体的双酚核心结构。trans-Chalcone 是有效的脂肪酸合酶 (FAS) 和 α-淀粉酶 (b>α-amylase) 抑制剂。trans-Chalcone 引起细胞周期停滞并诱导乳腺癌细胞系 MCF-7 凋亡。trans-Chalcone 具有抗真菌和抗癌活性。
体外研究

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.
反式-查耳酮价格(试剂级)
报价日期产品编号产品名称CAS号包装价格
2024/04/30A14734反式-查耳酮, 97%
trans-Chalcone, 97%
614-47-1100g520元
2024/04/30A14734反式-查耳酮, 97%
trans-Chalcone, 97%
614-47-1500g1924元
2024/04/30XW06144711反-查耳酮
trans-benzylideneacetophenone;benzalacetophenone;phenyl styryl ketone;(e)-1,3-diphenyl-2-propen-1-one;1,3-diphenyl-2-propenone;trans-chalcone;chalkone
614-47-125G149元
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