异甜菊醇
| 中文名称 | 异甜菊醇 |
|---|---|
| 中文同义词 | 异甜菊醇;ISOSTEVIOL 异甜菊醇;异甜菊醇、异斯特维醇;异甜菊醇, 来源于甜叶菊;异甜菊醇标准品;ISOSTEVIOL 异甜菊醇 标准品;异甜菊醇, BR;异甜菊醇对照品 |
| 英文名称 | ISOSTEVIOL |
| 英文同义词 | Isosteviol (NSC 231875);(4α,8β,13β)-13--Methyl-16-oxo-17-norkauran-18-oic acid;Ccris 6121;Nsc 231875;17-NORKAURAN-18-OIC ACID, 13-METHYL-16-OXO-, (4-ALPHA,8-BETA,13-BETA)-;ISOSTEVIOL;(4-alpha,8-beta,13-beta)-13-methyl-16-oxo-17-norkauran-18-oicacid;13-beta-kauran-18-oicacid,13-methyl-16-oxo-17-nor-8-bet |
| CAS号 | 27975-19-5 |
| 分子式 | C20H30O3 |
| 分子量 | 318.45 |
| EINECS号 | |
| 植物来源 | 甜叶菊 |
| 相关类别 | 标准品;提取物;中药对照品;植物提取物;对照品;标准品-对照品;对照品-中药对照品;二萜;标准品 -中药标准品;标准品，对照品;医药、农药及染料中间体;Chiral Reagents;Miscellaneous Natural Products;Intermediates & Fine Chemicals;Pharmaceuticals |
| Mol文件 | 27975-19-5.mol |
| 结构式 |  |
异甜菊醇 性质
| 熔点 | 228.0 to 232.0 °C |
|---|---|
| 沸点 | 455.6±38.0 °C(Predicted) |
| 密度 | 1.15±0.1 g/cm3(Predicted) |
| 储存条件 | Sealed in dry,Room Temperature |
| 溶解度 | DMSO:81.5(最大浓度 mg/mL);255.92(最大浓度 mM) |
| 形态 | 固体 |
| 酸度系数(pKa) | 4.69±0.60(Predicted) |
| 颜色 | 白色到近乎白色 |
| InChI | InChI=1/C20H30O3/c1-17-9-5-14-18(2)7-4-8-19(3,16(22)23)13(18)6-10-20(14,12-17)11-15(17)21/h13-14H,4-12H2,1-3H3,(H,22,23)/t13-,14?,17-,18+,19+,20-/s3 |
| InChIKey | KFVUFODCZDRVSS-MVXPDRGUNA-N |
| SMILES | C12CC[C@@]3(C(=O)C[C@@]1(CC[C@]1([H])[C@](C)(C(=O)O)CCC[C@@]21C)C3)C |&1:3,7,10,12,20,r| |
Isosteviol ((-)-Isosteviol) dose-dependently relaxed the vasopressin (10
-8
M)-induced vasoconstriction in isolated aortic rings with or without endothelium. However, in the presence of potassium chloride (3×10
-2
M), the vasodilator effect of isosteviol on arterial strips disappeared. Only the inhibitors specific for the ATP-sensitive potassium (KATP) channel or small conductance calcium-activated potassium (SKCa) channel inhibited the vasodilator effect of isosteviol in isolated aortic rings contracted with 10
-8
M vasopressin.
The attenuation by isosteviol of the vasopressin- and phenylephrine-induced increase in [Ca
2+
]i was inhibited by glibenclamide, apamin and 4-aminopyridine but not by charybdotoxin. Furthermore, the inhibitory action of isosteviol on [Ca
2+
]i was blocked when A7r5 cells co-treated with glibenclamide and apamin in conjunction with 4-aminopyridine were present.
Isosteviol (1-100 micromol/l) inhibits angiotensin-II-induced DNA synthesis and endothelin-1 secretion. Measurements of 2'7'-dichlorofluorescin diacetate, a redox-sensitive fluorescent dye, showed an isosteviol-mediated inhibition of intracellular reactive oxygen species generated by the effects of angiotensin II.
57817-89-7
27975-19-5
以(2S,3R,4S,5S,6R)-3,4,5-三羟基-6-(羟甲基)四氢-2H-吡喃-2-基((4R,4aS,6aR,9S,11aR,11bS)-9-(((2S,3R,4S,5S,6R)-4,5-二羟基-6-(羟甲基)-3-(((2S,3R,4S,5S,6R)-3,4,5-三羟基-6-(羟甲基)四氢-2H-吡喃-2-基)氧基)四氢-2H-吡喃-2-基)氧基-4,11b-二甲基-8-亚甲基十四氢-6a,9-甲基环庚[a]萘-4-羧酸酯为原料，通过10％硫酸水解反应，合成了Ent-16-氧代吡喃-19-酸。反应条件为常规水解条件，无需额外催化剂或特殊温度控制。产物经纯化后，收率为93％，熔点为228.4-230.8℃。通过IR、1H NMR、13C NMR和HRMS对产物进行了结构确认。IR谱显示特征吸收峰位于3448, 2955, 2924, 2848, 1736, 1692, 1453, 1404, 1373, 1320, 1268, 1214, 1180, 1150, 1108, 973, 950, 796, 589 cm-1。1H NMR (400 MHz, CDCl3) δ: 2.64 (dd, J = 18.64, 3.76 Hz, 1H), 2.17 (d, J = 13.40 Hz, 1H), 1.90-1.37 (m, 13H), 1.25 (s, 3H), 1.22-1.14 (m, 3H), 1.06-1.03 (m, 1H), 0.98 (s, 3H), 0.95-0.88 (m, 1H), 0.78 (s, 3H)。13C NMR (100 MHz, CDCl3) δ: 224.22, 184.33, 56.79, 57.62, 56.09, 54.83, 49.73, 49.59, 44.38, 42.02, 40.42, 38.99, 38.34, 32.80, 29.69, 22.32, 20.57, 19.55, 14.04。HRMS (ESI) m/z: [M + Na]+ 计算值C20H30O3Na 341.2093，实测值341.2085。
参考文献：
[1] Chemistry and Biodiversity, 2013, vol. 10, # 2, p. 177 - 188
[2] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 19, p. 2485 - 2490
[3] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 26 - 40
[4] Journal of Chemical Crystallography, 2009, vol. 39, # 2, p. 108 - 111
[5] Journal of Chemical Crystallography, 2011, vol. 41, # 4, p. 519 - 522
安全信息
| WGK Germany | 3 |
|---|---|
| 海关编码 | 2918.30.9000 |
| 更新日期 | 产品编号 | 产品名称 | CAS号 | 包装 | 价格 |
|---|---|---|---|---|---|
| 2025/12/22 | HY-N0872 | 异甜菊醇 Isosteviol | 27975-19-5 | 5mg | 100元 |
| 2025/12/22 | HY-N0872 | 异甜菊醇 Isosteviol | 27975-19-5 | 10mM * 1mLin DMSO | 110元 |