CAS Number118525-40-9
Synonyms3,5,7-Trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one; Icaritin; 3,5,7-Trihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-chromen-4-one; BIDD:ER0021; 3,7-dihydroxy-8-prenyl-4'-methoxychrysin; Anhydroicaritin
Molecular FormulaC21H20O6
Molecular Weight368.38
Density1.4±0.1 g/cm3
Boiling Point582.0±50.0 °C at 760 mmHg
Melting Point239ºC
Appearancelight yellow to dark yellow
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 118525-40-9 |
| Catalog No. | 2A-2189669 |
| Chinese Name | 去水淫羊藿黄素； 脱水淫羊藿素 |
| Synonyms | 3,5,7-Trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one; Icaritin; 3,5,7-Trihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-chromen-4-one; BIDD:ER0021; 3,7-dihydroxy-8-prenyl-4'-methoxychrysin; Anhydroicaritin |
| Molecular Formula | C21H20O6 |
| Molecular Weight | 368.38 |
| Density | 1.4±0.1 g/cm3 |
| Boiling Point | 582.0±50.0 °C at 760 mmHg |
| Melting Point | 239ºC |
| Appearance | light yellow to dark yellow |
| Water Solubility | DMSO: soluble5mg/mL, clear (warmed) |
| Storage Condition | 2-8°C |
| Application | Icaritin is a natural compound reported to have anti-cancer activity, possibly by regulating the MAPK/ERK/JNK and JAK2/STAT3/AKT signaling pathways. |
| PubChem ID | 11057945 |
| SMILES | COc1ccc(-c2oc3c(CC=C(C)C)c(O)cc(O)c3c(=O)c2O)cc1 |
| InChI | InChI=1S/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 |
| InChI Key | TUUXBSASAQJECY-UHFFFAOYSA-N |
| Hazard Symbols | transportation |
| Bioactivity | Icaritin(Anhydroicaritin) is a component of Epimedium flavonoid isolated from Herba Epimedii; enhances osteoblastic differentiation of mesenchymal stem cells (MSCs) while it inhibits adipogenic differentiation of MSCs by inhibiting PPAR-g pathway.IC50 value:Target: in vitro: Icaritin was unable to promote proliferation, migration and tube like structure formation by human umbilical vein endothelial cells (HUVECs) in vitro [1]. Icaritin potently inhibited proliferation of K562 cells (IC50 was 8 μM) and primary CML cells (IC50 was 13.4 μM for CML-CP and 18 μM for CML-BC), induced CML cells apoptosis and promoted the erythroid differentiation of K562 cells with time-dependent manner. Furthermore, Icaritin was able to suppress the growth of primary CD34+ leukemia cells (CML) and Imatinib-resistant cells, and to induce apoptosis [2]. icaritin strongly inhibited the growth of breast cancer MDA-MB-453 and MCF7 cells. At concentrations of 2-3 μM, icaritin induced cell cycle arrest at the G(2)/M phase accompanied by a down-regulation of the expression levels of the G(2)/M regulatory proteins such as cyclinB, cdc2 and cdc25C. Icaritin at concentrations of 4-5 μM, however, induced apoptotic cell death characterized by the accumulation of the annexin V- and propidium iodide-positive cells, cleavage of poly ADP-ribose polymerase (PARP) and down-regulation of the Bcl-2 expression [3].in vivo: In mouse leukemia model, Icaritin could prolong lifespan of NOD-SCID nude mice inoculated with K562 cells as effective as Imatinib without suppression of bone marrow. Icaritin could up-regulate phospho-JNK or phospho-C-Jun and down-regulate phospho-ERK, phospho-P-38, Jak-2, phospho-Stat3 and phospho-Akt expression with dose- or time-dependent manner [2]. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Natural Products >> Flavonoids Research Areas >> Cancer References [1]. Yao D, et al. Icaritin, an exogenous phytomolecule, enhances osteogenesis but not angiogenesis--an in vitro efficacy study. PLoS One. 2012;7(8):e41264. [2]. Zhu Jf, et al. Icaritin shows potent anti-leukemia activity on chronic myeloid leukemia in vitro and in vivo by regulating MAPK/ERK/JNK and JAK2/STAT3 /AKT signalings. PLoS One. 2011;6(8):e23720. [3]. Guo Y, et al. An anticancer agent icaritin induces sustained activation of the extracellular signal-regulated kinase (ERK) pathway and inhibits growth of breast cancer cells. Eur J Pharmacol. 2011 May 11;658(2-3):114-22. Chemical & Physical Properties Density 1.4±0.1 g/cm3 Boiling Point 582.0±50.0 °C at 760 mmHg Melting Point 239ºC Molecular Formula C21H20O6 Molecular Weight 368.380 Flash Point 206.7±23.6 °C Exact Mass 368.125977 PSA 100.13000 LogP 4.84 Appearance of Characters light yellow to dark yellow Vapour Pressure 0.0±1.7 mmHg at 25°C Index of Refraction 1.657 InChIKey TUUXBSASAQJECY-UHFFFAOYSA-N SMILES COc1ccc(-c2oc3c(CC=C(C)C)c(O)cc(O)c3c(=O)c2O)cc1 Storage condition 2-8°C Water Solubility DMSO: soluble5mg/mL, clear (warmed) |
| Use of | Properties Name 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one Synonym More Synonyms Icaritin Biological Activity Related Catalog Signaling Pathways >> Autophagy >> Autophagy Natural Products >> Flavonoids Research Areas >> Cancer References [1]. Yao D, et al. Icaritin, an exogenous phytomolecule, enhances osteogenesis but not angiogenesis--an in vitro efficacy study. PLoS One. 2012;7(8):e41264. [3]. Guo Y, et al. An anticancer agent icaritin induces sustained activation of the extracellular signal-regulated kinase (ERK) pathway and inhibits growth of breast cancer cells. Eur J Pharmacol. 2011 May 11;658(2-3):114-22. Chemical & Physical Properties Molecular Formula C21H20O6 Exact Mass 368.125977 PSA 100.13000 Appearance of Characters light yellow to dark yellow Index of Refraction 1.657 InChIKey TUUXBSASAQJECY-UHFFFAOYSA-N |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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