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578-74-5

中文名稱 芹甙元-7-葡萄糖苷
英文名稱 Apigenin 7-glucoside
CAS 578-74-5
EINECS 編號 209-430-5
分子式 C21H20O10
MDL 編號 MFCD00016787
分子量 432.38
MOL 文件 578-74-5.mol
更新日期 2025/08/05 10:50:48
578-74-5 結構式 578-74-5 結構式

基本信息

中文別名
芹菜素-7-葡萄甙
芹菜苷配基-7-O-葡糖苷
芹菜素-7-葡萄糖苷
芹菜甙元(芹菜素)-7-葡萄糖甙
芹菜甙元(芹菜素)-7-O-葡萄糖甙
芹菜素-7- O -葡萄糖苷
大波斯菊苷
芹菜甙元-7- 葡萄糖甙
芹菜甙元-7- O-葡萄糖甙
芹甙元-7-葡萄糖苷
英文別名
OSMIIN
COSMETIN
COSMOSIIN
APIGETRIN
Cosemetin
Cosmosioside
APIGENIN-7-GLUCOSIDE
Apigetrin, Cosmosiin
APIGENIN-7-O-GLUCOSIDE
Apigenin 7-β-D-glucoside
Apigenin 7-b-D-glucoside
Apigenin-7-O-β-D-glucoside
Apigenin 7-beta-D-glucoside
APIGENIN-7-O-GLUCOSIDE hplc
7-o-(beta-D-Glucosyl)apigenin
APIGENIN-7-O-GLUCOSIDE WITH HPLC
Apigenin-7-O-β-D-glucopyranoside
Apigenin, 7-beta-D-glucopyranoside
APIGENIN-7-GLUCOSIDE (COSMOSIIN)(P)
APIGENIN-7-O-GLUCOSIDE (COSMOSIIN)(P)
APIGENIN-7-O-GLUCOSIDE (COSMOSIIN)(SH)
Apigenin 7-glucoside SynonyMs:Apigetrin
7-O-BETA-D-GLUCOPYRANOSYLOXY-4',5-DIHYDROXYFLAVONE
4H-1-Benzopyran-4-one,7-(β-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)
4H-1-Benzopyran-4-one,7-(b-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-
7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one, 7- (.beta.-D-glucopyranosyloxy)-5-hydroxy-2-(4- hydroxyphenyl)-
4H-1-Benzopyran-4-one, 7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)- (9ci)
所屬類別
生物化工:中草藥成分

物理化學性質

外觀性狀白色結晶體,可溶于甲醇、乙醇、DMSO等有機溶劑,來源于廣藿香、仙鶴草,蓰草,構樹葉。
熔點230-237°C
沸點788.9±60.0 °C(Predicted)
密度1.642±0.06 g/cm3(Predicted)
儲存條件Inert atmosphere,2-8°C
溶解度DMSO(輕微,超聲處理),甲醇(輕微)
酸度系數(shù)(pKa)6.13±0.40(Predicted)
形態(tài)neat
顏色淡黃色至黃色
BRN65669
穩(wěn)定性吸濕性
InChIKeyKMOUJOKENFFTPU-YUVSVTSJNA-N
SMILESC1(C2=CC=C(O)C=C2)OC2=C(C(=CC(OC3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C2)O)C(=O)C=1 |&1:17,20,22,24,r|
LogP-0.040 (est)

應用領域

用途1
用于含量測定/鑒定/藥理實驗等。
藥理藥效:抗腫瘤、消炎、抗病毒。

安全數(shù)據

安全說明34/35
WGK Germany3
海關編碼29389090

制備方法

方法1
4H-1-Benzopyran-4-one, 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]-

119249-30-8

芹甙元-7-葡萄糖苷

578-74-5

在攪拌條件下,將化合物1(CAS: 119249-30-8,150 mg,0.25 mmol)溶于甲醇(20 mL)和30%氨水(5 mL)的混合溶液中。反應混合物在室溫下持續(xù)攪拌12小時。反應完成后,通過減壓蒸餾除去溶劑。所得殘余物通過硅膠柱色譜法進行純化,采用乙酸乙酯/甲醇(3:1,v/v)作為洗脫劑,得到目標產物5-羥基-2-(4-羥基苯基)-7-(((2S,3R,4S,5S,6R)-3,4,5-三羥基-6-(羥甲基)四氫-2H-吡喃-2-基)氧基)-4H-苯并吡喃-4-酮,為黃色固體(78 mg,收率72%)。產物的熔點為234-236°C(文獻值:238-239°C)。紅外光譜(KBr壓片,cm^-1)顯示特征吸收峰:3440, 2918, 1615, 1563, 1452, 1346, 1273, 1245, 1146, 1103, 1072, 1024, 895。核磁共振氫譜(400 MHz, DMSO-d6)δ:12.97(s, 1H, OH-5),10.48(s, 1H, OH-4'),7.96(d, J = 8.8 Hz, 2H, H-2', H-6'),6.94(d, J = 8.8 Hz, 2H, H-3', H-5'),6.87(s, 1H, H-3),6.83(d, J = 1.6 Hz, 1H, H-8),6.45(d, J = 1.6 Hz, 1H, H-6),5.42(d, J = 8.0 Hz, 1H, H-1),5.15(s, 1H, OH-2),5.08(s, 1H, OH-3),5.06(s, 1H, OH-4),4.63(s, 1H, OH-6),3.72-3.70(m, 1H, H-2),3.49-3.18(m, 5H, H-3,4,5,6)。核磁共振碳譜(100 MHz, DMSO-d6)δ:60.6, 69.6, 73.1, 76.5, 77.2, 94.8, 99.6, 99.9, 103.1, 105.4, 116.0, 121.1, 128.6, 156.9, 161.1, 161.4, 163.0, 164.3, 180.1。高分辨質譜(HRMS)計算值[M + Na]+ C21H20O10Na為455.3665,實測值為455.3649。

參考文獻:

[1] Tetrahedron, 2004, vol. 60, # 9, p. 2025 - 2034

[2] Carbohydrate Research, 2012, vol. 357, p. 41 - 46

知名試劑公司產品信息

芹甙元-7-葡萄糖苷價格(試劑級)
報價日期產品編號產品名稱CAS號包裝價格
2025/05/22HY-N0578芹甙元-7-葡萄糖苷
Apigenin 7-glucoside
578-74-51 mg409元
2025/05/22HY-N0578芹甙元-7-葡萄糖苷
Apigenin 7-glucoside
578-74-510 mM * 1 mLin DMSO904元
2025/05/22HY-N0578芹甙元-7-葡萄糖苷
Apigenin 7-glucoside
578-74-55mg950元

常見問題列表

生物活性
Apigenin-7-glucoside (Apigenin-7-O-β-D-glucopyranoside),ROS 清除劑,具有抗增殖,抗氧化活性。
體外研究

Apigenin 7-glucoside exhibits significant anti-proliferative activity against B16F10 melanoma cells after 24 and 48 h of incubation. Apigenin-7-glucoside provoks an increase of subG0/G1, S and G2/M phase cell proportion with a significant decrease of cell proportion in G0/G1 phases. Apigenin-7-glucoside enhances melanogenesis synthesis and tyrosinase activity of B16F10 melanoma cells.
Apigenin 7-glucoside specifically induces the differentiation of CD34 + cells towards the erythroid lineage and inhibited the myeloid differentiation. Apigenin 7-glucoside has strong antioxidant activity against reactive oxygen species (ROS) in vitro in a concentration-dependent manner.

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