118525-40-9
3,5,7-Trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
CAS: 118525-40-9;38226-86-7
Molecular Formula: C21H20O6
118525-40-9 - Names and Identifiers
| Name | 3,5,7-Trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one |
| Synonyms | ICARITIN icaritin Icaritin Cycloicaritin Anhydroicaritin b-Anhydroicaritin Icaritin, b-anhydro- Icaritin(Anhydroicaritin) 3,7-bis(2-hydroxyethyl)icaritin 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one 3,5,7-Trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one 3,5,7-Trihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one 4H-1-Benzopyran-4-one,3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)- 4H-1-benzopyran-4-one, 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)- |
| CAS | 118525-40-9 38226-86-7 |
| InChI | InChI=1/C21H20O6/c1-11(2)4-9-14-15(22)10-16(23)17-18(24)19(25)20(27-21(14)17)12-5-7-13(26-3)8-6-12/h4-8,10,22-23,25H,9H2,1-3H3 |
| InChIKey | TUUXBSASAQJECY-UHFFFAOYSA-N |
118525-40-9 - Physico-chemical Properties
| Molecular Formula | C21H20O6 |
| Molar Mass | 368.38 |
| Density | 1.359 |
| Melting Point | 239℃ |
| Boling Point | 582.0±50.0 °C(Predicted) |
| Flash Point | 206.7℃ |
| Solubility | DMSO : 14 mg/mL (38.00 mM; Need ultrasonic and warming);H2O : < 0.1 mg/mL (insoluble) |
| Vapor Presure | 3.82E-14mmHg at 25°C |
| Appearance | Yellow crystalline powder |
| Color | light yellow to dark yellow |
| Maximum wavelength(λmax) | 368nm(MeOH)(lit.) |
| pKa | 6.44±0.40(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.656 |
| MDL | MFCD22422519 |
| Physical and Chemical Properties | Yellow crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from epimedium. |
| In vitro study | Icaritin (4-64 µM; 48 hours; K562, imatinib-resistant cells and primary CML cells) treatment inhibits proliferation of K562, imatinib-resistant cells and primary CML cells . Icaritin (0-64 µM; 48 hours; K562 and primary cells) treatment induces K562 or primary cells apoptosis in an concentration dependent manner. Icaritin (32 µM; K562 cells) treatment increases cell population in the sub-G1 phase in K562 cells. Icaritin (0-64 µM; 48 hours; K562 cells) treatment inhibits MAPK/ERK/JNK downstream signaling and diminishes Jak2/Stat3/Akt expression. Icaritin treatment also significantly inhibits Bcl-2 protein expression and up-regulated Bax protein expression in K562 with a dose-dependent manner accompanied by the cleavage activation of caspase-3 or caspase-9, and a down-regulated expression of Apaf-1. Cell Proliferation Assay Cell Line: K562, imatinib-resistant cells and primary CML cells Concentration: 4 µM, 8 µM, 16 µM, 32 µM and 64 µM Incubation Time: 48 hours Result: Inhibited cell proliferation. Apoptosis Analysis Cell Line: K562 or primary cells Concentration: 0 µM, 4 µM, 8 µM, 16 µM, 32 µM and 64 µM Incubation Time: 48 hours Result: Induced K562 or primary cells apoptosis. Cell Cycle Analysis Cell Line: K562 cells Concentration: 32 µM Incubation Time: Result: Cell population in the sub-G1 phase was increased. Western Blot Analysis Cell Line: K562 cells Concentration: 0 µM, 4 µM, 8 µM, 16 µM, 32 µM and 64 µM Incubation Time: 48 hours Result: Inhibited MAPK/ERK/JNK downstream signaling and diminishes Jak2/Stat3/Akt expression. |
| In vivo study | Icaritin (4-8 mg/kg; intraperitoneal injection; daily; for 10 weeks; female NOD-SCID nude mice) treatment could prolong lifespan of NOD-SCID nude mice inoculated with K562 cells without suppression of bone marrow in mouse leukemia model. Animal Model: Female NOD-SCID nude mice (6-8 weeks old) with K562 cells Dosage: 4 mg/kg and 8 mg/kg Administration: Intraperitoneal injection; daily; for 10 weeks Result: Could prolong lifespan of NOD-SCID nude mice inoculated with K562 cells without suppression of bone marrow. |
118525-40-9 - Risk and Safety
| WGK Germany | 3 |
| RTECS | DJ3100870 |
| HS Code | 29329990 |
118525-40-9 - Reference
| Reference Show more | 1. Tu Shumei, Liu Yuping, Chen Yan. Icariin inhibits exosome-mediated lung metastasis of melanoma and its mechanism [J]. Journal of Pharmacy, 2021,56(03):778-785. 2. Pan, Xiu-Wu, et al. "Icaritin acts synergistically with epirubicin to suppress bladder cancer growth through inhibition of autophagy." Oncology reports 35.1 (2016): 334-342.https://doi.org/10.3892/or.2015.4335 3. Cheng, Tao, et al. "Comparative pharmacokinetics study of icariin and icariside II in rats." Molecules 20.12 (2015): 21274-21286.https://doi.org/10.3390/molecules201219763 4. Liu, Congyan, et al. "Icariin combined with snailase shows improved intestinal hydrolysis and absorption in osteoporosis rat." Biomedicine & Pharmacotherapy 94 (2017): 1048-1056.https:// doi.org/10.1016/j.biopha. 2017.07.163 5. [IF=5.878] Shumei Tu et al."Icaritin ameliorates extracellular microparticles-induced inflammatory pre-metastatic niche via modulating the cGAS-STING signaling."Phytotherapy Research. 2022 Mar 07 |
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