反式查爾酮
| 中文名稱 | 反式查爾酮 |
|---|---|
| 中文同義詞 | 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 |
| 英文名稱 | trans-Chalcone |
| 英文同義詞 | PHENYL STYRYL KETONE;2-BENZALACETOPHENONE;2-BENZYLIDENEACETOPHENONE;3-PHENYLACRYLOPHENONE;TRANS-BENZYLIDENEACETOPHENONE;TRANS-CHALCONE;1,3-DIPHENYL-2-PROPEN-I-ONE;1,3-DIPHENYL-3-PROPEN-1-ONE |
| CAS號(hào) | 614-47-1 |
| 分子式 | C15H12O |
| 分子量 | 208.26 |
| EINECS號(hào) | 210-383-8 |
| 相關(guān)類別 | 羰基化合物;醫(yī)藥中間體;有機(jī)原料;中間體;合成;格氏試劑;化工原料;有機(jī)中間體;化工中間體工業(yè)原料 |
| Mol文件 | 614-47-1.mol |
| 結(jié)構(gòu)式 |  |
反式查爾酮 性質(zhì)
| 熔點(diǎn) | 55-59 °C |
|---|---|
| 沸點(diǎn) | 208 °C25 mm Hg(lit.) |
| 密度 | 1.0712 |
| 折射率 | 1.5361 (estimate) |
| 閃點(diǎn) | >230 °F |
| 儲(chǔ)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 | 淡黃色低 |
| 氣味 (Odor) | 為 花香氣味 |
| 香型 | floral |
| 水溶解性 | Soluble in chloroform, ether, benzene, and ethanol (slightly). Insoluble in water. |
| Merck | 14,2037 |
| BRN | 509985 |
| 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+ |
| InChIKey | DQFBYFPFKXHELB-VAWYXSNFSA-N |
| SMILES | [H]\C(=C(\[H])C(=O)c1ccccc1)c2ccccc2 |
| LogP | 4.013 (est) |
| CAS 數(shù)據(jù)庫(kù) | 614-47-1(CAS DataBase Reference) |
| NIST化學(xué)物質(zhì)信息 | Benzalacetophenone(614-47-1) |
在氮?dú)庀拢瑢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?dú)饬髦袛嚢杌旌衔?6小時(shí)，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(wú)水Na2SO4干燥合并的萃取液，除去溶劑，在短時(shí)間快速柱色譜上純化粗產(chǎn)物得到反式-查耳酮。
trans-Chalcone 是從Aronia melanocarpa 果皮中分離出來(lái)的，是類黃酮前體的雙酚核心結(jié)構(gòu)。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(xì)胞周期停滯并誘導(dǎo)乳腺癌細(xì)胞系 MCF-7 凋亡。trans-Chalcone 具有抗真菌和抗癌活性。
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. |
安全信息
| 危險(xiǎn)品標(biāo)志 | Xn,Xi |
|---|---|
| 危險(xiǎn)類別碼 | 22-36/37 |
| 安全說明 | 22-36/37/39-45 |
| WGK Germany | 3 |
| RTECS號(hào) | UD5576750 |
| 海關(guān)編碼 | 29143990 |
| 存儲(chǔ)類別 | 11 - 可燃固體 |
| 危險(xiǎn)性類別 | 急性毒性 類別4 經(jīng)口 眼部刺激 類別2 特異性靶器官毒性-一次接觸，類別3 |
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