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480-44-4

中文名稱 金合歡素
英文名稱 Acacetin
CAS 480-44-4
EINECS 編號 207-552-3
分子式 C16H12O5
MDL 編號 MFCD00016936
分子量 284.26
MOL 文件 480-44-4.mol
更新日期 2024/12/19 16:50:44
480-44-4 結(jié)構(gòu)式 480-44-4 結(jié)構(gòu)式

基本信息

中文別名
金合歡素
刺槐黃素
刺槐素
5,7-二羥-4'-甲氧黃酮
阿卡西汀
洋槐素
5,7-二羥基-4'-甲氧基黃酮
英文別名
5,7-DIHYDROXY-4'-METHOXYFLAVONE
ACACETIN
LINARIGENIN
METHYL-4'-APIGENIN
5,7-dihydroxy-2-(4-methoxyphenyl)-4h-1-benzopyran-4-on
5,7-dihydroxy-4’-methoxy-flavon
5,7-dioxy-4’-methoxyflavone
acacetine
apisenin4’-methylether
buddleoflavonol
5,7-dihydroxy-2-(4-methoxyphenyl)-4-benzopyrone
Abietic
ACACETIN(METHYL-4'-APIGENIN)(RG)
5,7-DIHYDROXY-2-(4-METHOXYPHENOL)-1-BENZOPYRAN-4-ONE
1-BENZOPYRAN-4-ONE,5,7-DIHYDROXY-2-(4-METHOXYPHENOL)-
ACACETIN hplc
ACACETIN WITH HPLC
4'-O-Methylapigenin
5,7-Dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one
Linarisenin
所屬類別
天然產(chǎn)物:黃酮類化合物

物理化學(xué)性質(zhì)

外觀性狀黃色針狀結(jié)晶,可溶于甲醇、乙醇、DMSO等有機溶劑,來源于飛機草,大薊,金合歡。
熔點260-265 °C(lit.)
沸點346.76°C (rough estimate)
密度1.2160 (rough estimate)
折射率1.6200 (estimate)
儲存條件2-8°C
溶解度可溶于DMSO(輕微)、甲醇(非常輕微,加熱)
酸度系數(shù)(pKa)6.51±0.40(Predicted)
形態(tài)固體
顏色淡黃色至綠黃色至深黃色
最大波長(λmax)335nm(EtOH)(lit.)
Merck13,13
BRN277879
InChIKeyDANYIYRPLHHOCZ-UHFFFAOYSA-N
LogP2.443 (est)
CAS 數(shù)據(jù)庫480-44-4(CAS DataBase Reference)

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H315-H319-H335
危險品標(biāo)志Xi
危險類別碼R36/37/38
安全說明S26-S36
WGK Germany3
RTECS號DJ3002000
海關(guān)編碼29329990

應(yīng)用領(lǐng)域

用途1
用于含量測定/鑒定/藥理實驗等。
藥理藥效:舒郁,理氣,安神,活絡(luò)之功效。
用途2
金合歡素具有鎮(zhèn)靜,抗癌的作用。

常見問題列表

植物來源

金合歡 (Acacia farnesiana (Linn.) Willd.) (Mimosa) 豆科。灌木,高2-4米;枝具刺,刺長可達(dá)1-2厘米。二回羽狀復(fù)葉,羽片4-8對,每羽片具小葉10-20對,小葉片線狀長橢圓形。頭狀花序腋生,直徑1.5厘米,常多個簇生。莢果圓柱形,長3-7厘米,直徑8-15毫米。種子多數(shù),黑色。 花極香,供提取香精。 刺灌術(shù)或小喬木,二回羽狀復(fù)葉,頭狀花序簇生于葉腋,盛開時,好像金色的絨球一般。

	金合歡素的植物來源

生物活性
Acacetin (5,7-Dihydroxy-4'-methoxyflavone) 是一種口服有效的類黃酮,來自 Tephroseris kirilowii (Turcz.) Holub。Acacetin 停在 PI3Kγ 的 ATP 結(jié)合口袋中。Acacetin 導(dǎo)致癌細(xì)胞周期停滯,并誘導(dǎo)細(xì)胞凋亡和自噬。Acacetin 具有有效的抗癌和抗炎活性,有用于疼痛相關(guān)疾病研究的潛力。
體外研究

Acacetin (5,7-Dihydroxy-4'-methoxyflavone; 10-200 μM; 24 hours) decreases cell viabilities in a dose-dependent manner. Acacetin has little effect on human normal glial cell line HEB and non-tumorigenic epithelial cell line MCF-10A.
Acacetin (50-150 μM; 24 hours) causes G2/M cell cycle arrest and induces apoptosis and autophagy.
Acacetin (50-150 μM; 24 hours) leads to decreases in levels of PI3Kγ-p110, p-AKT, p-mTOR, p-p70S6K, and p-ULK in a dose-dependent manner.

Cell Viability Assay

Cell Line: Breast cancer MCF-7 cells, hepatocellular carcinoma SMMC-7721 cells, lung adenocarcinoma A549 cells, esophageal carcinoma Eca109 cells
Concentration: 10, 20, 40, 60, 80, 100, 150, 200 μM
Incubation Time: 24 hours
Result: Decreased cancer cell viabilities in a dose-dependent manner.
Had IC 50 values of 82.75?μM, 103.9 μM, 157.4 μM, 54.7 μM in MDA-MB-231, MCF-7, A549, Eca109 cells, respectively.

Cell Cycle Analysis

Cell Line: MDA-MB-231 cells
Concentration: 50, 100, 150 μM
Incubation Time: 24 hours
Result: Resulted in increase in percentage of cells at G2/M phase and decrease in percentage of cells at G1 and S phase in a dose-dependent manner.

Apoptosis Analysis

Cell Line: MDA-MB-231 cells
Concentration: 50, 100, 150 μM
Incubation Time: 24 hours
Result: Induced apoptosis.

Cell Autophagy Assay

Cell Line: MDA-MB-231 cells
Concentration: 50, 100, 150 μM
Incubation Time: 24 hours
Result: Induced autophagy.
Resulted in marked increases in EGFP-LC3 puncta formation and a dose-dependent accumulation of LC3-II.

Western Blot Analysis

Cell Line: MDA-MB-231 cells
Concentration: 50, 100, 150 μM
Incubation Time: 24 hours
Result: Resulted in decrease in levels of Bcl-2 and Bcl-xL and increase in levels of p53.
Led to decreases in levels of PI3Kγ-p110, p-AKT, p-mTOR, p-p70S6K, and p-ULK in a dose-dependent manner.
Had little or no effect on expression of PI3Kα, PI3Kβ, PI3Kδ, p-ERK, p-p38, and p-JNK.
體內(nèi)研究

Acacetin (5,7-Dihydroxy-4'-methoxyflavone; 5, 20 mg/kg/day; orally; for 3 days) significantly suppresses microglial activation in an LPS-induced neuroinflammation mouse model.
Acacetin (25 mg/kg/day; orally; for 3 days) reduces neuronal cell death in an animal model of ischemia.
Acacetin (1.8-56.2 mg/kg/day; ip; single dose) decreases visceral and inflammatory nociception and prevented the formalin-induced oedema.

Animal Model: Male C57BL/6 mice, 7 weeks of age
Dosage: 5, 20 mg/kg
Administration: Orally; once a day for 3 days
Result: Significantly suppressed microglial activation in an LPS-induced (ip; 5mg/kg) neuroinflammation mouse model.

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